The Rise of Fractional Tech Leadership: Perspectives from Industry Experts | The Pair Program Ep46

In this insightful episode, we dive into the evolving landscape of fractional tech leadership with two seasoned experts, Dan Maccarone and Matt Walnock. As co-founder of Charming Robot, Dan brings a wealth of experience as a fractional Chief Product Officer, while Matt, with nine years of mentoring and coaching cloud companies, offers invaluable insights as a fractional Chief Technology Officer.

Join us as we explore the nuances of fractional tech leadership roles, from aligning engineering and product with business objectives to integrating with teams and establishing trust. Our guests provide valuable perspectives on the market for fractional roles, the difference between fractional leaders and consultants, and the ideal stage of company seeking such expertise.Whether you're considering stepping into a fractional tech leadership role or seeking to understand its impact on organizational success, this episode offers practical advice and valuable insights from industry leaders at the forefront of innovation.

About Dan Maccarone: Dan is the co-founder of Charming Robot, a product design company based in NYC. For the past twenty years, he has been helping startups and media companies shape their online product strategy, including Foursquare, Rent The Runway, Jetsetter, The Block, Blade and Skift. His experience also includes television, music and print media, and he has worked with Late Night with Jimmy Fallon, Gawker, Saturday Night Live, Universal Music and The Wall Street Journal. One of his most noted projects was creating the original strategy and user experience for Hulu. Prior to Charming Robot, Dan co-founded the design agency Hard Candy Shell.

About Matt Walnock: As a consulting technologist with 28 years in the tech industry, Matt has spent the last 9 years mentoring, coaching, and leading early-stage and scaling cloud companies. His focus is on empowering teams, offering personalized guidance to navigate challenges in technology development. His experience includes roles as CTO, VP of Engineering, and Software Architect at companies like Microsoft, Parature, MCI/Verizon Business, and IBM, where he’s earned seven patents. Matt has a Bachelor of Science in Computer Science from Penn State University. He is the co-founder of Longitude 77, a company on a mission to elevate technology teams and optimize their strategic vision and engineering processes.

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Welcome to The Pair Program from hatchpad, the podcast that gives you

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a front row seat to candid conversations

with tech leaders from the startup world.

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I'm your host, Tim Winkler, the

creator of hatchpad, and I'm

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your other host, Mike Gruen.

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Join us each episode as we bring

together two guests to dissect topics

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at the intersection of technology,

startups, and career growth.

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Welcome

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everyone to The Pair Program.

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I am Tim Winkler here with Mike Gruen.

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Mike, we talked about a little

bit earlier, but, uh, we are.

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Uh, entering playoff hockey,

which is a great time of year.

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Uh, the drama is about to unfold

between, you know, both our squads

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matching up in the first series.

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Are you feeling, feeling confident?

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Are you feeling like you

guys, maybe you're sleeping

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Mike Gruen: on us a little bit?

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I don't think we're sleeping on you.

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Uh, no, I'm feeling pretty good.

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Uh, I mean, President's trophy.

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I know there's a lot of people who

think that's like a curse, but like,

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if you actually run the numbers,

it's not feeling pretty good.

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Um, I mean, whatever, it's,

it's the playoffs, it's like

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everything that's about you too.

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Tim Winkler: I'd be feeling good if I

was, you know, you never know what's

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going to happen, but you know, for, for

the listeners, I'm, I'm a big caps fan.

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Mike's a big Rangers fan.

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And by the time everybody listens to this,

uh, the series will probably be over.

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So it doesn't even matter

what you're saying.

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But, uh, the reality is,

uh, it's always cool.

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Cause like, I remember back to our first

episode, You know, uh, you're wearing

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your Rangers jersey and wearing a cap

jersey, so we'll have to, we'll have to

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do a, another episode here after the, the

victor is crowned, do some public shaming.

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But, uh, I'm, I'm pumped.

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We'll, we'll see if we can maybe

get together for, for a game.

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That'd be great.

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Yeah.

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See something in person.

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But, um, cool.

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Uh, so I'm excited for,

for today's episode.

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It's actually, you know, something

that we've, we've talked about,

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uh, on our previous episode, uh,

uh, about fractional, you know,

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a fractional CTO, but we're going

to dive a little deeper into this

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concept of fractional tech leadership.

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Uh, you know, it's an area that, you know,

uh, we at Hatch has, has seen really kind

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of take off and popularity in the startup

world over the last couple of years here.

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Um, and so we want to expand on it,

uh, and build a little bit of awareness

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for, you know, those listeners that

are maybe considering going down that

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path, or maybe we're already down that

path and, you know, want to, you know,

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maybe learn a little something extra.

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Uh, we've got a couple of, uh,

excellent guests joining us, um, today.

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So we've got a couple of folks

that have been navigating the,

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these waters for, for some time.

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And, uh, again, what we love about

our, our kind of format is we get

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to bring on two, um, two guests.

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To catch it from a couple

of different perspectives.

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So, uh, one, one of our guests

is, uh, you know, going to be

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taking the fractional CTO side.

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Uh, we've got Matt Walnock, uh, joining

us on that front and then taking

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it from the product perspective.

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Uh, we have Dan Macaron, uh, guys, thanks

both for joining us on The Pair Program.

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Dan Maccarone: And by the way,

I'm ready to walk off the podcast

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because I'm a Bruins fan and

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Tim Winkler: uh, so all right,

let's, let's just air horn,

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air horn this man out here.

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Dan Maccarone: Sucks to be you.

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Hey man, we can, we can

beat the Leafs I think.

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Tim Winkler: I'll fill you in on how

the, how the playoffs are going on

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our side and we'll compare notes.

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Um, so before we dive in, we, we,

we go through, uh, you know, our

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traditional, uh, first segment

pair me up where we rattle off a

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couple of compliments, complimentary

pairings, Mike, you usually TS off.

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Uh, what do you, what

do you got for today?

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Mike Gruen: So yeah, today I'm

going with a tea and cribbage.

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Um, so cribbage is a great card game.

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I learned it in college, um, to playing

it, play with my wife all the time.

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We drink tea.

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Uh, they just sort of go together.

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It's a nice, relaxing way

to, to spend an evening.

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Um, and, uh, yeah, so

that's my, that's my parent.

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I didn't know you

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Tim Winkler: were an 85 year old woman.

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This is great.

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Have we

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Mike Gruen: just met?

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I

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Tim Winkler: think

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Mike Gruen: you

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Tim Winkler: do.

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I was going to

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Mike Gruen: say maybe knitting.

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Yeah.

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I mean, you remember when I came

to the hockey game and we, I sat

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there knitting the entire time.

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Tim Winkler: Tea and cribbage.

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Yeah.

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Wow.

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That's epic.

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Um, I don't even know if I've

ever played cribbage before.

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Have you guys played cribbage before?

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I have, I have when I was 10.

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Is it like a two person, just two

people could play or is it multiplayer?

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You can play two, three or four.

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Okay.

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I don't have too many more

follow up questions to ask you.

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What kind of tea are

we drinking, Earl Grey?

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No,

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Mike Gruen: I just go, I'm simple.

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Irish breakfast or

something along those lines.

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English breakfast.

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I was gonna say like

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Tim Winkler: with whiskey and tea.

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Cool.

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All right.

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I'll, I'll hop in.

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So I'm gonna, I'm gonna go with

a, uh, a food pairing, um, with

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McDonald's and Krispy Kreme doughnuts.

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So this was, you know, just

recently announced this kind of

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this partnership between these two

fast food goats, in my opinion.

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I think it's a genius move.

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Um, but McDonald's will is.

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For those that don't know,

McDonald's will soon begin offering

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Krispy Kreme donuts on their menu.

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I think it rolls out

later, later this year.

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Is that because the ice

cream is always broken?

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Is that just coming out like soup?

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But, uh, you know, I grew up, it's a

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Dan Maccarone: glaze now.

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It just puts on a donut.

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It's nice.

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Tim Winkler: That's right.

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That's right.

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I mean, I grew up on Krispy Kreme donuts.

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I think it's, I think

they're, they're fantastic.

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And then, you know, I don't eat

McDonald's that often, but if I

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do, there's no doubt I'm going to.

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You know, be adding on

a Krispy Kreme donut.

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So I think it's smart, uh,

little pivot on their side.

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Uh, and now that that's out,

I've been seeing, you know, every

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other fast food chain kind of

offering something else similar.

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So like Wendy's popped up

and they're offering like

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Cinnabons as, as their thing.

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So.

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So anyways, that's, that's my parent.

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I'm have, have you guys, Krispy Kreme?

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Is that, how's that rank?

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If you're, are you a Boston guy?

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So are you a Duncan through and

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Dan Maccarone: through?

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I am a Boston.

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I don't need sweets.

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So donuts don't really mean much to me,

but I do like Duncan, uh, quite a bit.

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I like my coffee.

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My wife thinks it tastes like

swirl and we, um, don't go to

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the same coffee places now.

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Tim Winkler: I've been enjoying the,

the, the Dunking, uh, commercials.

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I think they're pretty creative.

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They're really fun.

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I agree.

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Um, cool.

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All right.

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Passing it along.

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Uh, Matt, how about a quick, uh, a quick

intro and then, uh, you're pairing.

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Matt Walnock: Yeah, very good.

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Um, so Matt Walnut, um, uh, with longitude

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nine years in a fractional capacity.

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I've got a partner that works in a

fractional capacity as with the CEOs.

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I work with, with the CTOs.

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Um, Pairing, I mean, the weather's

getting warm and things are getting green.

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I love being outside.

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So it's hiking and cold beer and

there's, there's a lot of breweries.

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I live in Northern

Virginia, just west of here.

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There's a, you know, throw a rock,

hit a brewery every, every 20 yards.

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Um, so there's plenty of options.

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Um, but.

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Yeah, it tastes better after

you've sort of climbed a hill.

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Tim Winkler: That's solid.

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I can totally agree on that.

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Have you, this is bear chase.

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Have you, uh, been out to bear chase?

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Matt Walnock: I was

just there last weekend.

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Yeah.

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Tim Winkler: Were you?

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Yeah.

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Did you do Raven's rock?

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Matt Walnock: No, we did

Raven's rock two weekends ago.

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We were, we were, um, uh, Sam

more shelter last weekend.

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It was cool.

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We did about a little section

of the roller coaster.

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Tim Winkler: Nice.

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My wife and I got married at,

uh, at bear chase at the house.

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That's connected to the, Oh, very nice.

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Yeah, it is.

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It's a really, really cool, cool brewery.

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But, um, I agree.

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It's something about, uh, a beer

just tastes so much more satisfying

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after, you know, taking on a hike of

some sort, but yeah, Good pairing.

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Good pairing.

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All right.

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Uh, Dan, we're, we're,

we're testing you here.

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You, uh, you're prepared.

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I got

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Dan Maccarone: it.

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I'm prepared.

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I got

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Tim Winkler: this.

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Dan Maccarone: Yeah.

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I agree.

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I love to carry a bunch of years in

my backpack to reach the end of a,

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uh, like, um, what's called a, When

you get the, the, the hike and you

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had to hike back, you can sit by the

lake, have a beer and then watch that.

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Oh, it's the best.

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It's the best.

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Not my pairing, but I'm, I'm with you.

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Um, so, uh, yeah, so, uh, Dan Macaron,

I, uh, I run a company called charming

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robot that is been kind of consulting

in product for about the past 14 years,

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but I've been doing the fractional.

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Chief product officer role for

about four, four and a half years.

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Um, and, and kind of still do a

lot of agency work on the side.

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But what I've found with the CPO is

that it can mean different things to new

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people, which I'm sure we'll dive into.

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Um, but my, my expertise has really been

about helping people launch their products

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and grow them for the first 18 to 24

months as a CPO, and then kind of finding

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my replacement as, uh, as I built the

team, but, um, yeah, that's My pairing

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is, uh, champagne and formula one racing.

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Uh, and the reason they go together

for me are my wife and I, and.

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A couple, another couple of friends of

ours, we watch all the races together.

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Um, not in person, we, we

zoom them or FaceTime them.

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And that when the race kicks off, we

pop a bottle of champagne on both sides.

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And every single race doesn't matter where

it is or what time of day or night it is.

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And generally it's.

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Not a time you want to be awake.

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Uh, but we drink the bottle of champagne

over the course of the hour of the race

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until they pop the champagne at the,

uh, at the, uh, at the end of the race.

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So it's a pairing.

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That's like been a big, a big part of,

uh, that, that tradition for a while now.

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And I, uh, feel like it.

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It fits into this, this, uh,

really you guys have created.

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Tim Winkler: Nice.

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Yeah, that's solid.

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Yeah.

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Most formula one, or is it a

lot of international races?

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Dan Maccarone: Yeah.

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You get a few in North America, like in

Austin or Vegas, uh, Montreal, but you,

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you know, like the one this weekend is

3am it's in China, uh, which, you know,

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it doesn't, it doesn't, it doesn't work

well on the East coast, but, you know,

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it's, you know, it's, it's, you know,

it's, it's, it's, it's, it's, it's.

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It can be fun sometimes you have a 3 a.

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m.

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total darkness and you're popping a

bottle of champagne, you know, it's great.

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Tim Winkler: Is the, the iconic race

I always associate with like kind of

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like a bougie ness, is that Monaco?

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Dan Maccarone: Yeah, Monaco is, is I

think the last race of the year and

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it's, it's uh, it's a, it's a cool one.

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It's in the city, it's not a

track, it's like you're racing

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around Monaco, it's really awesome.

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I've never been like, I'm

not, I was going to say,

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Tim Winkler: it's like the a list of

celebrities all make it to Monaco,

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Dan Maccarone: like 20, 000 a ticket.

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Like I'm, I'm okay.

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I can watch it on ESPN.

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It's totally fine.

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Tim Winkler: Yeah.

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I like it.

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Champagne and formula.

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One.

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I didn't see that coming.

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You, you, uh,

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Dan Maccarone: I feel like a

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Tim Winkler: peasant with McDonald's now.

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I

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Mike Gruen: just feel like I'm a.

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I mean, it is nice to see that they're,

yeah, they're not trying to do, uh,

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health food, like, you know, right, right.

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Tim Winkler: Uh, cool.

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All right.

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Well, let's, uh, let's transition,

uh, into the heart of the discussion.

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So again, you know, we're going

to be peeling back the curtain

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on fractional tech leadership.

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Uh, some of these areas that, that

we're going to be discussing are, you

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know, kind of defining what it means,

uh, to be a fractional CTO or, or CPO.

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Uh, specifically how, how each role is

maybe aligning, uh, engineer and product

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with key, key business objectives,

um, breaking down, uh, like the key

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stakeholders that, that you all are

interacting with and, and also how

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you integrate with the existing teams.

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Um, I'd love to understand a

little bit more about, you know,

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what metrics define success.

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Um, I know Mike's got a slew of other

things here, but, um, and then I'd like

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to also close with just a little bit of

like, you know, let's, let's talk about,

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you know, what we think the fractional

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Um, so the easiest way to kind of

kick this off, I think is just.

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Uh, you know, starting with both, you

know, each of you is we'll start with

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you, Matt, uh, and just from like

the fractional CTO point of view,

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you know, giving us an example or

some reasons when and why a founder,

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you know, loops you, you and you

or, or your, your, your counterpart.

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Matt Walnock: Yeah, happy to, um,

It's a, there's a range of situations,

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um, but largely it's to answer the

question of why isn't my product

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what I thought it was going to be.

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It's, it's a miss in the,

you know, the expectation.

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I work with largely, um,

early stage companies.

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Some of them have just received

their funding and they want to be

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pointing in the right direction.

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Others are through it and not.

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Sort of necessarily seeing the results

they expected so that they can identify

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that maybe something's wrong, but the what

is actually going on and what is wrong.

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Um, that's where somebody like myself,

having seen a number of teams doing

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this for the, the last nine years, um,

as well as prior experience, can kind

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of step in and say, all right, let's,

let's step back from the whole situation.

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Let's look at the team and the process

and how everything's being decided.

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And more often than not, it's, it's a,

it's a, it's gaps in, in, in that process,

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either, you know, at the beginning where

it's so critical to get requirements well

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refined and, um, on point, especially

when you're in a situation often where the

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founder is the, uh, the sort of the anchor

and the engineering team may be offshore.

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You know, that translating the founder

vision to that engineering team via

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those requirements is always critical.

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So that's, that's usually a gap and

then kind of the other end, the quality

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of the operation, and usually it's,

it's situations where they've made

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decisions or had leadership that hadn't

had the experience or got caught off

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guard by some things, or they've had

success in a lot of cases, they've

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had to grow in certain areas and had

to leave other others behind for.

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For the limited resources they've

run, but for me, it's, it's

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largely being able to step in and

go, okay, what, what's missing?

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What, what, what isn't being

fully fulfilled here from a

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software delivery perspective?

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Tim Winkler: Sure.

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And, and we'll, uh, dissect that more,

uh, before I kick over to Dan, though,

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I do have a quick question on, uh,

the bulk of the, um, uh, companies are

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the founders that you're collaborating

with all the bulk of them coming from,

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you know, more of like a go to market

background versus a technical background.

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Matt Walnock: Most of the folks

that I work with, yes, um, they're,

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they're, they're in need of that good

technical partner at the beginning.

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And if there can't be that for

themselves, they're, they're often

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leaning on maybe somebody that can

author the code maybe has run a team,

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but isn't sort of at that level of

business acumen to kind of translate

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what the business needs into the actions

the engineering team needs to take.

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Sure.

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Tim Winkler: Perfect.

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Uh, and Dan, let's kick

it over to you real quick.

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So, you know, talk, talk to us a

little bit more about when and why,

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you know, you're being brought in,

uh, to, uh, uh, to an organization.

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Dan Maccarone: Yeah, I think

there are two scenarios that tend

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to work best for me as a CPO.

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One is, you know, early stage company.

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pre launch.

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Um, they really need to, you have a

founder, who's probably a subject matter

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expert and really knows the problem they

want to solve, but may not know how to

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translate that into an actual experience.

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And so for me, it's like coming on board,

helping, like listening to them, and

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then working with them and their CTO.

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And they have another CRO

or someone who's part of it.

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They're going to translate that into an

actual overall, like, UX and design, uh,

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and work with a CTO to get it launched

and help, help evolve that product after

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launch to see what's working, what's

not probably also partnering with a

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marketing person, a road person, uh,

with the first, you know, like, uh,

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18, 24 months while growing their team.

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Uh, it's really important as part of

the, to me as a fractional CPO to find

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the right people who can work full

time while I'm not there full time.

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But the reason they want

to hire me is because.

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I bring an expertise with the amount of

companies I've helped launch over the past

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couple of decades to, um, to do things

faster and quicker and put a process

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into place that's going to work for them.

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The other audience is some, a company

doesn't even have to be a startup,

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but usually it's probably a smaller

company that exists, but is, has either

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gone off the rails or is going in or

is going up the rails and really needs

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to rethink their approach to product

and approach this digital strategy.

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So coming in there often

means a few things.

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And it's kind of similar to

something you said, Matt, like.

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It's reassessing where they're at,

you know, what's, what's wrong, what's

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the problem, what's your North star.

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And then it's looking at the team and

saying, this is not the fun part and

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saying, who's right for this company?

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She's not, what do you guys need?

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What's missing?

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What's your process?

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Like, do you need a new

process or a process at all?

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Which often it's the latter it's

you have nothing going on and you

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need to get something in there.

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Um, and implementing that.

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And hopefully, you know, you can do

that one in like six to eight months.

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I often find that those are the ones

that move faster, but because they have

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a product that just needs some adjusting.

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But you still need someone who

can come in with an outside

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eye who's not a consultant.

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I think that's a really important thing.

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They're not a consultant.

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They're part of the team.

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They're just part of the team that

just happens to not work, you know,

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40 hours a week, but is doing the

work to get the change kind of

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implemented and get everything on

the right track until a new person

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comes in and fill that full time role.

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I think

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Mike Gruen: that's an important point

that I, that was like one of my questions.

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I think a lot of people have is how

do you differentiate Fractional from

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other types of whether it's consulting

or contracting type work, um, you

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know, I'll let both of you answer.

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Um, you know, Dan, if you

want to take it first,

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Dan Maccarone: I mean, yeah, Matt,

I'm really curious as you've been

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doing this for as much longer than I

have, but the most important thing.

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But one of the most important things

to me is having buy in from that

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kind of C level, um, or overall C

suite, that you are part of the team.

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And that needs to be

communicated to everyone else.

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If there's not buy in from the top,

it does not work in my opinion.

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Like, like you, because people,

I think, if they think you're

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fractional, think you're not focused.

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On the product, and I've actually had,

I've had founders said to me, if you

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don't think about this like 60 hours

a day, then you don't really know what

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it's like to be part of this company.

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And I'm like, well, that's not true.

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In fact, I think it's good that I'm

not thinking about it 60 hours a day.

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So what I am thinking about it, everything

else that's kind of contributed to my

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thoughts is letting me focus on this.

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But that, but that buy in is

so critical because it is a

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bit of a controversial space.

413

I mean, Matt, I don't

know what you believe in.

414

Matt Walnock: Yeah, I mean, when I, when

I meet my, my clients for the first time,

415

starting to get their know their teams,

I treat it like I'm onboarding as if

416

I were their full time CTO, I have to

emote that I have to show the actions

417

I'm taking, I have to kind of start to

understand their culture because the

418

first, I mean, the timing you described

there, Dan is right on that six to eight

419

month window, but those first 30 days

of onboarding and observation, it's

420

not about like, Immediately coming in

and making changes and fixing things.

421

It's getting up next to the team and

understand how they operate and how

422

they can be changed and what, what's

safe to lean on and what's, what's not.

423

And that's to me is the same as if I was

joining them full time, I very quickly

424

get into the mode of saying, you know,

we have issues and we have challenges.

425

And, you know, the support from the

top is, I agree, completely necessary.

426

Tim Winkler: And I, and I imagine too,

that the level of transparency that

427

the founding team is having with the

rest of the team about what's happening

428

here is pretty essential, right?

429

I could feel like if I was an

engineer and you know, you're coming

430

in and you're, you know, you're,

you're, you're asking questions and

431

everything about, you know, processes

and just doing that discovery phase.

432

Um, if I wasn't really, truly clear that,

you know, Hey, look, we're, we're bringing

433

in this fractional, you know, resource.

434

I want you to treat them as if, you

know, like, you know, is, is our CTO, but

435

just knowing like, this is a fractional

individual, like, are you coaching them

436

on how they communicate that to the

team or, you know, because you've maybe

437

seen it time and time again, this might

be their first engagement with one.

438

So how, how are you all, um, I guess this

kind of leads into that next question

439

about like that integration with the

team and, you know, what steps are

440

being taken to ensure more of this like

seamless kind of process flow for you.

441

Matt Walnock: Yeah, I mean, absolutely.

442

It's, it's, it's really

important to get that right.

443

The introduction to the team is

once you've got the support from the

444

leadership, um, the next right in line

is, is the team willing to work with you?

445

So it's, you know, uh, you know,

taking up a non threatening posture.

446

I'm here to help.

447

We're going to work together closely

and here's what we can achieve together.

448

And it's really sort of selling

them as a team that it's worth

449

their time to pay attention to

things that I might have to say.

450

Tim Winkler: How about

451

Dan Maccarone: on

452

Tim Winkler: the product side, Dan?

453

Dan Maccarone: Yeah, I don't, I don't

know that it has to be communicated

454

as this person is fractional.

455

It can be, I think it's, you know, I

think it's okay to tell people that,

456

but I also think that they, if you

have the support of leadership, it

457

should be, here's our product lead and.

458

You know, for the most part, you're

working remotely at this point anyway.

459

So it doesn't, I mean, I don't, I don't

devote hours, specific hours to clients.

460

I'm available whenever they need them.

461

I had my, I might be working on

something else and they hang me

462

or by working for them, but like.

463

To me it's about, this is the person

who's running this, and I'm building

464

a team or working with a team.

465

And so, I don't, I don't like

to be thought of as someone who

466

may not be available mentally

or physically for someone.

467

I think it's more like, I just

happen to be paid fractionally.

468

You know, that's how I look at it.

469

I don't know, I don't know.

470

Matt, can I ask you, like, do you,

Do you think that that makes sense

471

or do you think it's important to

communicate the practical side?

472

I don't want to hijack your show.

473

Matt Walnock: This is what we want.

474

I think it's well, I mean, I have to, it's

more getting into the process with them

475

and sort of showing that I'm going to be

a partner to their current leadership.

476

Um, engineering, that might be a director.

477

It might be a architect, a

team leader of some sort.

478

Cause that's it.

479

It's just important that there's

some instant credibility so we can

480

get to work and that that comes from

just me working with that leader.

481

And in a lot of cases, that's

just what I'm there to do.

482

It's a one on one with

that engineering lead.

483

And that's the level

of engagement we're at.

484

And then from there, it's me and the

team were, you know, a full interim role.

485

Where it's more of what Dan's describing

where it's like, okay, you'll report

486

to me now I'm taking the title.

487

It's I would be labeled interim CTO.

488

Not a lot more communication

needed other than that.

489

Leadership has support and we go to work.

490

But in those cases where there's,

we're looking to keep everybody

491

in place, we're looking to grow

and scale and augment this team.

492

Then getting a good partner just

at that team level team leadership

493

level is really important.

494

And, and for me, Dan, I I would just

finally say that the sort of the

495

boundaries for me are a little bit, I

need to make them more clear 'cause I

496

run right into like operational roles

and touching production systems and

497

things like that, that I need to be,

have bright lines around when I engage.

498

Tim Winkler: I was just gonna say, I'd

imagine too that, you know, for some

499

of these scenarios there could be, uh,

nego an offer to like, hey, like yeah,

500

if it's an interim role, if it goes well

and you like this as well, like you could

501

truly become our full-time, CTO, um.

502

So you, you, you don't want to kind

of spoil that and just kind of like,

503

maybe just set the stages is like, yeah,

you know, here's our, I've been asked

504

Matt Walnock: more than once, but I

try to go into these things with like,

505

no, let's just think of this as the

temporary condition that it's going to be.

506

And we're here to make this a better

situation for the next person.

507

And I talk more about how the

transition will occur and make sure

508

the client understands what the

vision is for this, not get used

509

to me doing this part time for you.

510

I think that's so

511

Dan Maccarone: important

512

Matt Walnock: because I,

513

Dan Maccarone: I definitely have that

same position where people have said to

514

me, so I know you're doing the scratching

right now, but when are you going to

515

be full time person and it's like,

I'm not, that's not what we agreed to.

516

And, and it can become quite

frustrating because they're, that

517

means they're not thinking about

you in the role that they should be.

518

They're thinking about you as someone

who is part time or as a consultant.

519

And that's clearly, you know, not

what Matt's doing, not what I'm doing.

520

Um, and when, I think when you start

having those questions again and again,

521

you have, you have to ask yourself,

is this the right place for me?

522

I don't mean full time.

523

I mean, they're asking

you to be full time.

524

I mean, it's a compliment in some

ways, but it's also like, guys, you got

525

to know people you're going to know,

like, this is not, that's not the.

526

Matt Walnock: I mean, I've, I've

worked with clients where we

527

had to have that conversation.

528

And it's like, we're, we've, we've done

the part where we fix the things and now

529

it's time to move on and get somebody in

here and, and we need to wind it down.

530

Tim Winkler: Matt, you kind of touched on

this briefly, uh, when you're answering

531

the previous question, but you know,

what, what does the, uh, snapshot of the

532

engineering team look like when you're

stepping into some of these engagements?

533

You mentioned there might be a

head of engineering or like a

534

lead engineer or an architect.

535

Uh, what's the What's the common thread

that you see in terms of, you know,

536

what that next hierarchy of a, of a

tech individual internal looks like.

537

Matt Walnock: Um, generally like

small team and most recently

538

it's, it's almost always a mix of

onshore and outsourced engineers.

539

Um, and the state they're in is usually

there's enough process there that it

540

got the attention, it got the funding.

541

And now it's, it's a moment of

decision on how to scale it.

542

Is it, you know, bring on more of the

outsource team higher locally restructure

543

is the architecture going to support

a lot of questions, um, in the air.

544

And when I can start to offer as a

sounding board to that, that leader and

545

say, there's here's options, let's talk

through options and give them a space

546

where they're not doing that in front

of their team or in front of their boss.

547

And we're hashing it out.

548

In the background, building their

confidence, and then we help package

549

that up for delivery with the team that

gets us into talking about process.

550

So there's, if you kind of aim right

at what do you need to deliver?

551

And that could be based

on the product vision.

552

It could be based on the road.

553

It could be contracts that they've

written and made customer commits.

554

And this, this individual is being

told, you know, I need to lead this

555

group forward and grow this product.

556

Usually it's in a moment where

they've never had to grow at

557

that rate or in that way before.

558

Tim Winkler: Dan, how about

yourself on the product side?

559

Are you seeing a product team

currently in place traditionally?

560

Or is there no, you know, lack

of any sort of a product team?

561

Dan Maccarone: For an early

562

Tim Winkler: stage startup,

563

Dan Maccarone: usually there isn't one.

564

Um, usually I try to, I think that

like on the products that you generally

565

you're building a product, you don't

need a full time team on day one.

566

I think that you do over time.

567

And so what I try to do is use my network

of design and UX resources to, you know,

568

find the right people to start, um,

get that product built over, let's say.

569

Somewhere between 8 to 10, 8 to 12

weeks, uh, and then once you launch,

570

you're going to spend some time learning.

571

You can't immediately go into

the next sprint because you

572

don't know what's working.

573

So if you had a full time designer

sitting there doing nothing,

574

it's kind of a waste of money.

575

But I do think that as you planned

out your roadmap and you're looking

576

at things, you know, you start to see

where you're going to need that full

577

time designer or full time UX person or.

578

Full time PM, whatever it might

be, and you kind of layer them in.

579

And I think by the end of the first

year, at that point, you should have a

580

full time person, at least in design,

or at least, you know, um, if you're

581

head of product, if you're me and you're

head of product, maybe you hire a part

582

time PM or a full time PM, because

they can kind of work on the day to

583

day, you know, details of things.

584

Um, but by the time I leave,

I, I, I kind of like to have

585

a full suite of product team.

586

Um, ready to go, uh, at larger companies

or when I come in kind of mid midway

587

through a company's journey, there usually

is, you know, some people are some people

588

on staff and there's probably a reason

I brought in some of them are probably

589

not going to stay and some of them are,

um, and then it's about building out the

590

right team, uh, filling in the gaps where

they exist and, and, uh, and keeping the

591

people who are may may have been like have

been hampered down before and have all the

592

talent, but just weren't able to use it.

593

And so giving them an opportunity to.

594

To really discover, you know, themselves

and get even better at their job.

595

So, uh, that's a great thing is

when you find someone who actually

596

has that talent and you get to

bring them up a little bit and get

597

them excited about the job again, I

598

Mike Gruen: mean, I think that's

one of the things that's really

599

different, like at startups between

say engineering and product is

600

like in the early days, startup.

601

Your CEO, the founders, they're

the product people, right?

602

And you're probably coming in and

really helping them take what that

603

vision and translate it into something.

604

Whereas if you have a technical

founder, they're doing the engineering

605

and now it's, it's sort of helping

them on the business side of things.

606

Not some, you know, they sort of

understand they've been through this,

607

this before they understand like

what a good process looks like, but

608

maybe they've never been responsible

for it or, or whatever else.

609

I imagine that's a big difference.

610

Um, like with regard to like, Matt, you're

pairing, you know, you're working with the

611

engineering leader, whereas, and maybe in

talk, I'm sure to the CEO or whoever, but

612

you're a little more focused on the team.

613

Whereas I'm sure Dan, you're probably

more working with in that gap between.

614

The CEO and the engineering team and

what they probably have a technical

615

founder or CTO or somebody who

you're working pretty closely with.

616

Dan Maccarone: I think it depends,

you know, for me, oftentimes it's

617

helping the founder and this can

be in concert with the CTO, by the

618

way, it depends on the company.

619

But like, oftentimes I find that.

620

If I get to have work with a good

CTO, it's the CTO and myself educating

621

the founder more than anything else.

622

Um, and that education isn't

education around their vision.

623

Obviously they have this idea

of what problem they're solving.

624

It's about.

625

Focus.

626

It's about what, like how to prioritize

things and how not to try to boil the

627

ocean and, and often how not to take right

turns and keep on the path that you've

628

set forward before you even get launched.

629

So that's the biggest thing I

always find is you have wonderful

630

founders with great ideas who.

631

You know, hear about something

that can make the product even

632

better and immediately want

to add that to the roadmap.

633

And you have to be like, look, that

impact product that impact engineering

634

and probably impact marketing.

635

Like, yes, let's do that in six months,

you know, and so those conversations

636

that no one wants to have, but you

got to have are a big part of the job.

637

Um, and it allows, you know, the team

designers, I'm sure that's true on the

638

engineering side too, to get their work

done and not get distracted by things that

639

are kind of shiny objects, you know, yeah.

640

Matt Walnock: Very much so.

641

Yeah.

642

I mean, I often find there's folks

that it's an absence of folks like

643

Dan in the role and you're asking the

engineering lead to stretch themselves

644

all the way to that CEO's vision

and bring back something tangible

645

for those engineers to work on and.

646

I've been asked more often than not.

647

What does a product manager do, Matt?

648

I try to answer that question.

649

I try to demonstrate a few things,

but there's very much a gap,

650

especially when the founder is a

product center wants to be connected

651

to the customer and the application.

652

It feels like they

really want to own that.

653

It's difficult sometimes to say,

Hey, you need a partner to just

654

help you refine that before we

can even Start building the other.

655

So the other

656

Dan Maccarone: thing that's like, I don't

know if you see this, but like, I've

657

noticed this more and more and maybe

it's just, as I get older or let's say

658

I get more experienced, is that a way of

putting it is, uh, that, uh, um, a lot

659

of people are afraid to say no to a CEO.

660

And this is true of big

companies as well as companies.

661

And I was just working on a project

recently where I was a functional

662

practical CPO, and I was talking to

the, one of the marketing people.

663

The CEO had asked for something and

she was like, yeah, I got to do that.

664

I'm like, wait, why did,

why are we doing this?

665

That makes no sense.

666

And she's like, well, he asked for it.

667

And I was like, it's okay to, it's

okay to, you know, uh, question it.

668

Like, just because it's an idea

doesn't mean it has to happen.

669

And she's like, well, I don't feel

comfortable doing that because, you

670

know, I have many of that long, whatever.

671

And I was like, wow, it really, and I've

heard this before and I've seen this

672

before and I'm like, wow, there really,

it really does need to be someone there to

673

kind of help the people who can't say no.

674

Maybe we don't feel comfortable or don't

feel like it's appropriate or whatever,

675

but you've got to be able to have that

conversation and say, listen, Like this

676

needs to be tabled or this isn't right,

or let's have a conversation about this.

677

I'm being negative.

678

I don't mean to be negative,

but like, I mean, I think

679

Mike Gruen: I found when I was,

so I was interim VP of product.

680

I've been, you know, whatever.

681

I found my job was more often than not

like, yes, but like, and it's back to

682

what I think you were saying before,

which is, yeah, that's a great idea.

683

Let's do it in six months or like, here,

let me pull off the roadmap and okay,

684

let's work together and figure out where,

like, where does this actually line up?

685

Um, and then the CEO is always

like, I hate when you do this.

686

I'm like, yeah, Cause you know,

we have to prioritize, like,

687

welcome, welcome to the world.

688

Matt Walnock: And a lot of times

they've been spending those resources

689

in the engineering group without

even really how much realizing how

690

much any of it was really costing.

691

So part of this is surfacing, just the

velocity, the capacity, the dollars going

692

into that saying, do you really want to

spend those dollars this way, or should

693

we focus on the contracts and customers?

694

I mean, opportunity

695

Mike Gruen: cost is a huge one that.

696

You have to bring up a lot like,

okay, cool, we can do that.

697

But you do realize that that means we're

not doing this, this, this, and this.

698

And that means this, you know, all

the things that come from that.

699

Matt Walnock: So I find there's

revelation just in kind of putting

700

all that out on the table in front

of them and going, here's value,

701

here's cost next to resources next

to the value you're intending to get.

702

And that's what having a partner person,

a product person as a partner to do that.

703

It's just, it's night and

day and the experience.

704

Tim Winkler: What's the average,

you know, length of engagement,

705

Matt, that you find yourself in?

706

I know it's kind of a broad question, but,

um, you know, you, again, like I think

707

we kind of alluded to this earlier, you

know, you, they don't want to be on life

708

support here, fractional life support.

709

So what, what kind of, uh, timelines are

you, when you go in and you're scoping

710

something, you know, what are, what are

you usually suggesting some examples?

711

Matt Walnock: Usually we'll break down

something like, you know, that observable

712

observation period, getting to know

them as like a 30 day kind of a window.

713

And then we can move

into planning and fixing.

714

And that is aligned with

what Dan said earlier.

715

It's like a six to eight months before

you can really have the impact and be

716

changing, you know, what's going on.

717

But a lot of these have just

a very long tail on them.

718

I've been with clients that I still talk

to for years and we're in Slack together.

719

And it's more.

720

You know, touch base every quarter type

of a scenario, but the, you know, full

721

attention to sort of interim CTO roles.

722

Those are 6 months to 2 a year.

723

And by the time we get to that

3rd quarter, we're, we're both

724

looking at each other going.

725

Okay, let's start putting the

process together to do the higher.

726

Tim Winkler: From an actual amount of

time that you're spending on, uh, the

727

engagement itself, does it, is it like

heavy in the front end and then it starts

728

to wean down, uh, as you get further along

in the engagement or is it just, you know,

729

part time, like, yeah, I don't know, 20

hours a week or any sort of like, uh, Or

730

do you not even do hourly and just make

it about milestones and deliverables?

731

I

732

Matt Walnock: try to do

just a monthly retainer.

733

So I, similar to what Dan was

describing earlier, that I can, I

734

can chop up my day how I need to,

to get to, to get to everybody.

735

Um, so I, I do, I mean, I put in a lot

of hours, but it's, it's, it's largely

736

based on the style of that engagement.

737

So I'll have like one large one that

I'm focused on and then maybe one

738

or two coaching or mentoring type of

arrangements, and then some maintenance

739

stuff with folks that I touched with.

740

Touch base with much less frequently

in terms of the level of effort.

741

And over the time, it's like getting

on board that observability period.

742

That's, that's kind of nice.

743

We're getting to know everybody, but,

and then it gets busy and then you're,

744

then you're really cranking on the

problem space and you're trying to

745

keep up with a, a fully running team.

746

Um, um, not breaking what they're

doing while helping them, you

747

know, turn in the right direction

and make some positive change.

748

Tim Winkler: So those timelines kind of

align with you, Dan, and on your side.

749

Dan Maccarone: Yeah.

750

And I try to do one to two kind of

bigger clients at a time and then

751

have smaller ones on the side.

752

Uh, my, my timeline generally is, is.

753

I would, I try to do like a 12 month

engagement because I do think that

754

once you start seeing results, like

Mark was saying, you can spend a lot

755

of time fixing more things and, and

seeing, you know, what's working,

756

what's not and hone your strategy.

757

Um, but, you know, I think after like 18

months is my max, you know, my, I mean,

758

my max to say, you got to replace me.

759

Uh, I do love those clients.

760

You stay, you're always kind of.

761

Working with what I often find is that

I'll kind of come back and work on

762

smaller projects with them afterwards

on things that are much more focused,

763

um, or like little strategy pieces

in concert with whoever's running

764

product and marketing like I'm not a

marketer, but these are working as well.

765

But I do, and I love those

relationships because they can

766

last for years and years and years.

767

But for that, like really heavy

lifting piece of it, it's, uh,

768

it's about 12 months digging team.

769

And I think, you know, to

Mark's point, like from Matt's

770

point, like, you know, the.

771

The, um, uh, the, the, the first 30 days,

by the way, the first 30 days is the

772

happiest time because everyone is like,

you know, ah, we're in this together.

773

And then, you know, you start

having those harder conversations

774

and, um, which is not a bad thing.

775

It's like, I think it's quite fun

to get into like actual strategy

776

and getting that stuff done.

777

But it is like.

778

You know, it's not all lollipops

and milkshakes, you know, it is

779

something else, you know, important.

780

Missed an opportunity for, for

pairing or tea and cricket.

781

I was going to

782

Mike Gruen: go with McDonald's and

Krispy Kreme, but it's actually a

783

quarter pounders and Krispy Kreme.

784

Dan Maccarone: It's not all

quarter pounders and Krispy Kremes.

785

I mean, it could have, it could

have been tea and cricket also,

786

I will say not, not you know.

787

I don't know.

788

I don't know.

789

Tim Winkler: I'm curious to know, uh,

when are the, when are these scenarios

790

where you're turning away the engagement,

because I think that's helpful maybe

791

to understand, you know, this good.

792

Personal fit here, the skillset fit.

793

Um, I'd imagine financials have a big

part to play into that, but, uh, generally

794

curious, like what are some of the,

the immediates that can maybe pop up

795

and you're like, this, this isn't going

to be a good, this isn't good for a

796

fractional CTO or fractional product lead.

797

Dan Maccarone: Um, I

mean, red flags for sure.

798

There's a lot of red flags that

come up and it's around, you

799

know, it's our own expectations.

800

It's, I always try to get a good sense of.

801

What is the vision of this person?

802

Not just like, what is their vision

for their product, but what are

803

their expectations for the next,

you know, six months, 12 months

804

and who else they're going to

involve in this experience, right?

805

Like, how have they

thought about marketing?

806

How have they thought about technology?

807

You know, um, how did that all revenue?

808

That's a big part of what

they're doing because.

809

If they want to, I go back to saying,

if they want to blow the ocean and they

810

can't be convinced otherwise, then that's

not something I want to be a part of.

811

If they, if they, um, if they think they

know more about technology than they do,

812

then I don't want to be involved with

them because they're not going to listen.

813

And it's how much they, they actually

trust, you know, my experience.

814

And I certainly am not saying that I'm

right all the time, because I'm not.

815

Bye.

816

To me, like, I, I believe that the

philosophy of trust your generals or

817

lieutenants, like, if ever I figure it's

like I come to Matt and say, Matt, let's

818

talk about this and we end up on the same

page that we go to a CEO and that CEO has

819

no interest in listening to us because it

doesn't align with that person's needs.

820

Like North star, even though like

we've done all the research and if that

821

happens once, fair enough, but if it

happens like six times and that you

822

can tell this in an early conversation

with someone, I don't, there's no

823

point in working with that person.

824

Cause you're never going to be affected

whether you're a program or not.

825

But like, to me, I'm working

with four or five clients.

826

I'd rather work with four or five clients.

827

We're going to listen to what, not

just me, but like the team I bring

828

to the table, you know, has to offer.

829

And they're generally pretty experienced.

830

Um, and it's willing to

have that conversation.

831

Not again, to say that we're going to

dictate what the right answer is, but

832

at least to be like, Listen to what

we're saying, that's my biggest point of

833

playing what they don't want to listen,

then I, I know that it's not like,

834

Mike Gruen: I think the way I, I

phrased that just like, is the idea

835

of like strong opinion, strongly held

versus strong opinions, loosely held.

836

I'm fine with somebody who's got

strong opinions, loosely held, right?

837

Like, I can change your mind.

838

If you've got strong opinions,

strongly held, there's just no

839

point in having this conversation.

840

Right?

841

Dan Maccarone: Right.

842

And I think, you know,

oftentimes that happens.

843

I like to do a small project with someone

first to just the appearance alignment.

844

Right.

845

And sometimes that's a lot of research.

846

And if I come back with research, the

data that says something that either

847

agrees with what they're saying, or

it's slightly off, or maybe totally is

848

like, yeah, he's actually over here and

there, and there is no listening to that.

849

That's a big, big red flag.

850

It's like, you're not going

to listen to the data.

851

If you don't listen to

data, then what are we here?

852

Tim Winkler: Matt, how about yourself?

853

And maybe also another thing to really

add on there is like, you know, the,

854

the stage of the products and, um, you

know, when, when is it too soon for you?

855

Matt Walnock: I mean, I don't not, not

to be repetitive, but the receptivity

856

to what you're saying and how

you're coming to these conclusions.

857

I mean, it's not, you

have to show your work.

858

You have to convince and support

and put the, put the data behind it.

859

But if you don't have a

receptive audience, you're

860

not going to get very far.

861

Um, you know, other things that, that come

to the top of the list on the engineering

862

side, I start to look at compliance.

863

Um, I start to look at obligations.

864

They've got outstanding and

their ability to meet them with

865

the tech they've got deployed.

866

Yeah.

867

Um, we start to look at how

they're handling their data.

868

It just, you start to get into some

very sensitive things very quickly,

869

depending on which vertical they're in.

870

Um, and, and sometimes I've been, you

know, revealing things to leadership.

871

They didn't know we're there, which is an

interesting situation to find yourself in.

872

Um, But for the most part, it's all, it's

all just trying to get transparency to

873

what is being run, how it's being operated

in a, in a space where you, the leadership

874

can see it, start making decisions.

875

Um, so it's, it's just, if you're not

able to kind of surface that in a way

876

that they can understand, that's the

other thing is if you're dealing with

877

a non technical COVID, sometimes it's

really have to put this into a space where

878

you're, you're literally at the whiteboard

for a few hours, just breaking it all

879

down and trying to show dependencies

between Decisions, um, can kind of blow

880

their hair back from time to time when,

when, when you get there, but again, if

881

you can, if you can synthesize and here's

what we can do about it, which is your

882

real value for being there, then sort

of the shoulders come down the street.

883

You can see the stress kind of come

off of them and like, okay, we can

884

do something about all of this.

885

That's great.

886

Let's go.

887

Tim Winkler: What about product stage?

888

Like, uh, I'm just generally curious,

like, are you, when are you coming in?

889

Or it's like, um, What, like

when's the earliest that

890

you've, you've kind of come into

891

Matt Walnock: an engagement?

892

Um, well, I mean, the absolute

earliest was, you know, it was,

893

it was a founder and a developer.

894

That was a very good idea too.

895

They needed some, yeah, no, but the

more, the more typical is, um, yeah,

896

they're, they're in that, you know.

897

Early stage money, series a, maybe I've

worked with a couple of companies that

898

were, you know, 250 to 500 million in

revenue, but that's few and far between.

899

Most of them are much, much, much smaller.

900

I, I like to just get it.

901

And again, when I walk in

there, it's not about, you know,

902

I'm here to do a job for you.

903

It's, it's more, I'm here to help you

over a period of time in your existence

904

and what's the right level of attention

and detail and what's the process.

905

So.

906

I'll talk to anybody having to meet them.

907

And a lot of times it's, it's handing

them off to maybe to somebody like Dan

908

to say, Hey, you don't need me yet.

909

You need somebody like that to kind

of get your roadmap put together,

910

get the vision, go figure out if the

market is even receptive before you

911

start spending engineering dollars.

912

Mike Gruen: How much time do you think

you guys are spending educating your

913

perspective client on what fractional

means and what they're actually

914

getting or by the time you're having,

or they've already sought you out

915

and maybe they know what they're,

they know what fractional means.

916

And so maybe you're not doing that

education because I've talked to a lot

917

of different people in the space and.

918

There's varying, uh, amounts of

education from their perspective.

919

Dan Maccarone: It's a lot up front.

920

It's a lot up front.

921

I mean, at least for me, I mean, I still

think that it goes back to people not

922

understanding the difference between

a consultant and a fractional person.

923

Uh, and, and even if you explain

it to them, I think there's

924

often this skepticism of, but are

you really a part of the team?

925

Um, and I work with so many early

stage companies that I think that it's

926

not just explaining to them, but it's

convincing them and their investors.

927

You know, their investors are

often skeptical that they can't

928

get a good product to the market

with someone who's fractional.

929

And you know, as someone who ran,

I ran agencies for 16 years where

930

we were doing the exact same thing.

931

We just had a team.

932

We thought of our team as our team,

the product, even the box, even getting

933

agent, um, investors on board with hiring.

934

An agency that could actually get the

thing launched faster than trying to

935

hire a team internally was a challenge

until we had until we could prove it.

936

We proved we have four problems

and look at all these things

937

we've launched that have actually

been successful with our work.

938

But I'm a fraction of the same challenge.

939

It's like.

940

You have, but in the end,

like, Matt, I'm sure you've had

941

this experience more than me.

942

It's, you gotta, it's asking

them to have faith in T'Challa.

943

Either they're gonna trust

the idea or they're not.

944

And there's not so much education

as um, understanding and faith.

945

Matt Walnock: Yeah, I agree with that.

946

It is.

947

It is a lot of upfront education, but

I find that once we get started, once

948

there's action being taken, results

being shown that we don't talk about

949

it much anymore, I tend to from time

to time, I mean, it does come up in

950

like the hours that we're working.

951

Like, I'm not going to be available

afternoons in some case, but for the most

952

part, it's, they don't really see me as

fractional once we start working together.

953

Um, and, and I have to sometimes

remind them to go, yeah, I have another

954

client that I'm doing a thing for.

955

I'll see you in a week.

956

And yeah, yeah.

957

Yeah.

958

It tends to just fade into the background.

959

Mike Gruen: Yeah, I figured.

960

But I mean, like at the, at the very

beginning, like when you're first starting

961

setting up that engagement, the sense I'm

getting is that they really don't know

962

what you are doing a lot upfront in terms

of education on what this role looks like.

963

It's not a well enough known.

964

It's not like, I feel like

people understand like a

965

fractional CFO very well.

966

And at this point, like they would

seek that out and they wouldn't have

967

in their head, they wouldn't need to be

educated about what that kind of means.

968

Matt Walnock: I just try to not

keep the label on it for too long

969

and just quickly get to thank you

for introducing me to your team.

970

I'm going to work with this named

individual on these sets of things

971

and your team will see this.

972

And this is the bubble we

call fractional CTO for you.

973

And once they can understand what

to expect, it goes a long way.

974

And again, the label

just sort of goes away.

975

It's now Matt's working with

the engineering team and we're

976

going to do good things together.

977

Awesome.

978

Tim Winkler: And to counter that

too, I think, you know, this leads

979

into another, the kind of like last

question, um, on the topic, but

980

they've probably done some research

to get referred to you to this point.

981

Um, I, I, I.

982

Mike and I were talking about this about

like, you know, how, how are you, how

983

are you sourcing, you know, new work?

984

Right.

985

And I've always seen that

it's usually very, very much.

986

It's just a referral network, right?

987

You did something for

this person over here.

988

They know another founder over there

that's in a similar type of, um, debacle.

989

And they're like, Oh, I used Matt.

990

How, how are you sourcing

your, your, your opportunities?

991

Uh, or are there other outlets out

there that maybe folks aren't privy to?

992

And, um, you know, You can keep

it secret if you want to keep that

993

resource a little golden nugget

to yourself, but I'm curious.

994

Dan Maccarone: I mean, I,

my whole business, my entire

995

career has been through word

of mouth and through referrals.

996

Uh, I don't do any marketing

or advertising other than stuff

997

like this or my own podcast.

998

But even that is generally like

about kind of a layer upon a layer.

999

And so there's always, I would say

95 percent of the time it's, I have a

00:48:18,040 --> 00:48:20,340

contextual warm introduction or referral.

00:48:20,620 --> 00:48:23,180

Um, and I like it that way.

00:48:23,240 --> 00:48:26,030

Uh, I find it so hard to.

00:48:26,495 --> 00:48:30,925

Convince someone who's never heard of

fractional or doesn't trust consultants

00:48:30,925 --> 00:48:34,904

or whatever, um, again, different

things, uh, to, to persuade them, I

00:48:34,904 --> 00:48:38,294

mean, even with a portfolio that I

have, which I'm very proud of, but.

00:48:38,705 --> 00:48:41,035

Um, yeah, that's, that's how

I've always done business.

00:48:41,035 --> 00:48:43,645

I've never done any

sort of, um, marketing.

00:48:44,075 --> 00:48:44,425

So you don't

00:48:44,425 --> 00:48:48,075

Mike Gruen: have like a big LinkedIn

campaign reaching out to, no,

00:48:48,724 --> 00:48:52,074

Dan Maccarone: no, no, I would, I

would, I don't, I, that makes me like

00:48:52,075 --> 00:48:53,434

want to throw up like the idea of doing

00:48:56,494 --> 00:48:57,085

people do it.

00:48:57,085 --> 00:48:58,445

I, I LinkedIn's huge.

00:48:58,445 --> 00:49:02,265

I, I, I don't even like, I don't even

like putting job postings on LinkedIn

00:49:02,265 --> 00:49:06,495

for people I want to hire because you

just get a, just a sea of people, like

00:49:06,495 --> 00:49:08,345

a fire hose of people so far fast.

00:49:08,395 --> 00:49:10,745

And you're like, well, I can't do these.

00:49:10,755 --> 00:49:14,014

So I tend to like use the same thing

when I'm looking for someone, I

00:49:14,015 --> 00:49:16,365

do it in my network and I'm like,

who's going to be great at this?

00:49:16,395 --> 00:49:17,745

And I get three or four people.

00:49:17,745 --> 00:49:20,339

And usually one of them is that diamond

in the rough you're looking for.

00:49:22,450 --> 00:49:23,580

Matt Walnock: That's

been my experience too.

00:49:23,670 --> 00:49:26,790

It's a lot of, a lot of warm leads

and doing good work for folks and

00:49:26,790 --> 00:49:29,240

your name gets around and then

you get some, you know, you're,

00:49:29,240 --> 00:49:31,910

you're walking in with credibility,

having done good work for folks.

00:49:31,910 --> 00:49:32,140

And

00:49:33,079 --> 00:49:36,120

Tim Winkler: have you guys seen

an uptick in, uh, inbounds,

00:49:36,390 --> 00:49:38,340

uh, in the last year and a half

00:49:38,449 --> 00:49:39,230

Matt Walnock: or two?

00:49:39,230 --> 00:49:42,090

A lot more receptivity to it.

00:49:42,190 --> 00:49:42,590

Yes.

00:49:42,590 --> 00:49:45,510

I think it's, they've been asked

to talk to a lot more folks and

00:49:45,510 --> 00:49:48,690

introduced to a lot more companies

in the last couple of years.

00:49:48,740 --> 00:49:49,570

Yeah, definitely.

00:49:51,400 --> 00:49:52,230

Dan Maccarone: Yeah, I think that's right.

00:49:52,230 --> 00:49:54,459

I think it's, it's more that the

idea that people are actually.

00:49:55,145 --> 00:49:59,875

Considering fractional people versus

not, um, and I certainly think that

00:49:59,985 --> 00:50:02,905

there are rules that they're considering

fractional and rules are not as well.

00:50:03,004 --> 00:50:07,435

Like, they're like, definitely, um,

I see a lot more fractional CMOs and

00:50:07,435 --> 00:50:11,895

I see CBOs, for example, um, but I

think that just means we're at the

00:50:11,895 --> 00:50:17,859

beginning of this kind of, for lack

of a better word, movement, um, I

00:50:18,820 --> 00:50:22,679

Tim Winkler: think paired with

a pretty drastic change in

00:50:22,680 --> 00:50:24,840

venture funding, uh, no doubt.

00:50:24,869 --> 00:50:30,959

And a bit in a tighter grasp on, uh,

you know, budgets, uh, has certainly,

00:50:30,970 --> 00:50:36,570

you know, created a wave of things,

one, uh, a downtick and hiring up larger

00:50:36,590 --> 00:50:38,360

engineering teams that maybe wants.

00:50:38,725 --> 00:50:44,045

Would have done to more folks offshoring

or outsourcing development, and then three

00:50:44,085 --> 00:50:49,535

more, more engagement with consulting

or fractional types of, uh, resources.

00:50:49,584 --> 00:50:51,115

I've seen that across the board.

00:50:51,355 --> 00:50:53,775

I don't know if that's been

some of the themes that you all

00:50:53,775 --> 00:50:55,444

have seen, you know, as you're.

00:50:55,980 --> 00:51:00,240

Building your teams, if they're,

you know, are they less has you

00:51:00,470 --> 00:51:02,510

maybe maybe it's still too soon.

00:51:02,510 --> 00:51:06,270

But have you seen a shift of

folks maybe wanting to come off of

00:51:06,300 --> 00:51:10,489

outsource development or staying on

the path of outsource development?

00:51:10,489 --> 00:51:14,280

Because, you know, for financial

reasons or anything like that.

00:51:17,250 --> 00:51:20,770

Matt Walnock: I don't think that's changed

a lot for the companies that I work with.

00:51:20,770 --> 00:51:22,480

It's always had an outsourced component.

00:51:22,500 --> 00:51:23,320

Most of them do.

00:51:23,450 --> 00:51:30,299

Um, I have seen, um, uh, interestingly

enough with, um, AI, I get a lot of folks

00:51:30,299 --> 00:51:34,289

now wanting to have those conversations,

um, even if their product wasn't

00:51:34,289 --> 00:51:35,890

necessarily pointed in that direction.

00:51:36,349 --> 00:51:39,260

Um, so we start talking

about growing the team.

00:51:39,270 --> 00:51:40,770

Where do those skill sets come from?

00:51:40,780 --> 00:51:42,960

But it's much more specialized than it is.

00:51:43,400 --> 00:51:45,300

I need a front end developer,

back end developer.

00:51:45,995 --> 00:51:46,335

Yeah.

00:51:47,505 --> 00:51:47,775

Dan Maccarone: Yeah.

00:51:47,775 --> 00:51:49,115

And the product that

it's not the same thing.

00:51:49,115 --> 00:51:51,515

I mean, at least I still see where you're

saying that, which is the outsourced.

00:51:52,745 --> 00:51:57,405

Dev team, but when it comes to designing

UX, I don't usually as one person

00:51:57,455 --> 00:52:01,725

that is somewhere domestic, doesn't

have to be in New York where I am.

00:52:01,725 --> 00:52:04,994

But, um, yeah, I don't, we haven't,

we haven't really outsourced that

00:52:04,995 --> 00:52:06,724

and I don't think ever really.

00:52:08,495 --> 00:52:08,644

Tim Winkler: Yeah.

00:52:08,644 --> 00:52:10,615

I've seen downtick in, in product roles.

00:52:10,795 --> 00:52:16,675

Um, as far as like, you know, we used

to see a lot more of them, uh, those

00:52:16,705 --> 00:52:21,145

product teams kind of being a little bit

more trimmed down, uh, you know, Across

00:52:21,405 --> 00:52:24,365

some of the series, a series B startups.

00:52:25,005 --> 00:52:28,105

Um, but again, I think there's a

lot of that's just an aftermath of

00:52:28,325 --> 00:52:34,264

a different economic time as well.

00:52:34,264 --> 00:52:35,824

As far as I think it's awesome because

00:52:36,275 --> 00:52:37,734

Mike Gruen: you have trimmed

down engineering teams.

00:52:37,734 --> 00:52:42,335

I mean, it's one of those things where

there's a ratio of the number of people.

00:52:42,710 --> 00:52:46,190

Engineers and the number of product

managers and if you're trimming down

00:52:46,190 --> 00:52:49,300

the engineering side, you probably

don't need as many product people.

00:52:50,040 --> 00:52:50,150

Dan Maccarone: Yeah.

00:52:50,310 --> 00:52:53,749

I mean, you don't need, I think that

the number of people to make a good

00:52:53,750 --> 00:52:57,420

product team, isn't a lot, especially

for a startup, even in a series,

00:52:57,440 --> 00:53:01,020

they're like, you just don't need that

many designers or UX people or PMs.

00:53:01,040 --> 00:53:04,220

Like, you know, I mean, as you get

bigger, for sure, as you have different

00:53:04,390 --> 00:53:05,510

protocols, whatever, have them PM.

00:53:05,510 --> 00:53:06,100

So that makes sense.

00:53:06,100 --> 00:53:10,240

But like you can survive as a

startup to a certain extent with

00:53:10,240 --> 00:53:13,670

like one designer, one UX person.

00:53:14,115 --> 00:53:17,335

Maybe not even one full time

UX person for a long time.

00:53:17,485 --> 00:53:21,755

Um, and when you add that second

designer, you better be hoping

00:53:21,765 --> 00:53:22,911

you have a lot of work for them.

00:53:22,911 --> 00:53:24,905

It's like, you know, I mean,

the way I was hiring, I'm sure

00:53:24,905 --> 00:53:26,065

this is not like a new idea.

00:53:26,075 --> 00:53:29,764

It's like, you want that person to

be personally at the seams so that

00:53:29,764 --> 00:53:33,335

when you hire that next person,

there is that, that need for that.

00:53:33,335 --> 00:53:33,535

Right.

00:53:33,545 --> 00:53:35,165

Not that I want to, I never

want to overwork people.

00:53:35,165 --> 00:53:36,255

I believe in work life balance.

00:53:36,255 --> 00:53:39,955

I actually hate companies that don't,

it makes me angry, but I do believe

00:53:39,955 --> 00:53:43,615

that you need to like, Be smart

about hiring and not waste money.

00:53:43,615 --> 00:53:46,805

And when people are sitting there

doing nothing, it's, it's pretty,

00:53:46,975 --> 00:53:47,945

it's, it's a lane for everyone.

00:53:47,945 --> 00:53:48,815

Cause they get bored too.

00:53:48,885 --> 00:53:50,155

You don't want your team being bored.

00:53:52,155 --> 00:53:54,714

Mike Gruen: You know, I, uh, you

can definitely survive a long time

00:53:54,715 --> 00:53:56,604

with a very thin product team.

00:53:56,774 --> 00:53:59,295

Um, you have the right

senior engineers in place.

00:53:59,464 --> 00:54:01,065

They can do a lot of that translation.

00:54:01,065 --> 00:54:04,045

Um, They take on a lot of ownership.

00:54:04,055 --> 00:54:05,015

I totally agree.

00:54:05,155 --> 00:54:08,455

Like the, some of the worst places

I've worked have way too many product

00:54:08,485 --> 00:54:10,055

people and not enough engineers.

00:54:10,505 --> 00:54:14,765

Um, just, we spent a lot of time

talking about the work that we could

00:54:14,774 --> 00:54:16,824

be doing, or we could do the work.

00:54:21,405 --> 00:54:24,695

Tim Winkler: Well, I know that we've got

a couple of minutes left, so, um, Mike,

00:54:24,705 --> 00:54:25,985

did anything else you wanted to add?

00:54:25,985 --> 00:54:28,555

Uh, yeah, I think we covered quite a bit.

00:54:28,565 --> 00:54:32,175

That was really, really informative

and, uh, you know, really helpful stuff.

00:54:32,175 --> 00:54:34,465

So appreciate you guys

shedding light on it.

00:54:34,485 --> 00:54:38,975

Let's, let's transition to a, to our

final segment, the five second scramble.

00:54:38,984 --> 00:54:43,114

So just a quick kind of rapid fire

on, uh, some Q and a some business,

00:54:43,125 --> 00:54:48,895

some personal, um, Mike, you, you lead

us off, uh, with Dan and then Matt,

00:54:48,895 --> 00:54:50,815

I'll, I'll jump off, jump with you.

00:54:51,205 --> 00:54:51,415

So,

00:54:51,415 --> 00:54:52,335

Mike Gruen: yeah, so let's do this.

00:54:52,565 --> 00:54:53,105

Yeah, let's do it.

00:54:53,105 --> 00:54:53,415

You ready?

00:54:53,515 --> 00:54:53,755

All right.

00:54:53,755 --> 00:54:54,664

Here we go.

00:54:54,845 --> 00:54:55,215

All right.

00:54:55,685 --> 00:54:59,245

Uh, explain fractional leadership

as if I were a five year old.

00:55:00,995 --> 00:55:04,485

Dan Maccarone: So, you know how

you have a teacher that comes to

00:55:04,485 --> 00:55:07,365

your school every day and you have

to spend time with that teacher?

00:55:08,035 --> 00:55:11,584

Well, imagine if that teacher

had to teach multiple students

00:55:11,585 --> 00:55:13,324

at once, but it was individually.

00:55:13,325 --> 00:55:15,585

So they teach you, they teach

your friend, they teach your other

00:55:15,615 --> 00:55:16,965

friend, but they're going to spend.

00:55:17,400 --> 00:55:20,690

Three hours a day with each of you,

but every single day you get to spend

00:55:20,790 --> 00:55:24,450

time with that teacher and ask them

anything you want and you get their

00:55:24,450 --> 00:55:27,490

full attention for that time period

and the next day and the next day.

00:55:27,895 --> 00:55:29,415

That's what I do, but with companies,

00:55:29,875 --> 00:55:30,475

Mike Gruen: that's awesome.

00:55:30,495 --> 00:55:33,445

Although I don't think you get three hours

cause there's 30 kids in the class, but

00:55:35,505 --> 00:55:36,755

Dan Maccarone: it's a

private Montessori school.

00:55:42,435 --> 00:55:43,335

Practically cheap, man.

00:55:44,625 --> 00:55:46,824

Mike Gruen: What, what's your

favorite stage company to work with?

00:55:48,224 --> 00:55:48,364

Dan Maccarone: Great.

00:55:48,424 --> 00:55:49,094

Uh, early stage.

00:55:49,195 --> 00:55:53,205

I love, I love pre product to, uh,

to, to taking a idea from nothing

00:55:53,205 --> 00:55:53,955

and bringing it to something.

00:55:55,190 --> 00:55:57,650

Mike Gruen: Uh, what's the

biggest challenge or what do you

00:55:57,660 --> 00:56:01,620

think is the biggest challenge

00:56:02,790 --> 00:56:04,170

Dan Maccarone: in general

tech exec leaders?

00:56:04,570 --> 00:56:09,759

Uh, I think it's, I

think it's marrying the.

00:56:10,305 --> 00:56:14,685

The vision you're trying to create

to an actual product that's going

00:56:14,685 --> 00:56:18,734

to resonate with users because

there's so much out there right

00:56:18,735 --> 00:56:20,545

now overwhelming people with tech.

00:56:20,555 --> 00:56:21,995

And I don't care what industry it is.

00:56:21,995 --> 00:56:25,814

If you look at AI as just one example,

like everyone's launching an AI company.

00:56:25,814 --> 00:56:27,305

So why does yours matter?

00:56:27,635 --> 00:56:30,935

And I think the question that someone

always has to ask is why does this matter?

00:56:31,325 --> 00:56:32,145

What am I solving?

00:56:32,365 --> 00:56:34,225

And why does someone want to

use this versus something else?

00:56:34,225 --> 00:56:36,145

And every leader needs to

be asking that question.

00:56:36,415 --> 00:56:37,785

Otherwise they shouldn't be doing the job.

00:56:38,355 --> 00:56:38,625

Absolutely.

00:56:39,580 --> 00:56:42,090

Mike Gruen: Um, what's the best piece

of advice you've ever been given?

00:56:44,380 --> 00:56:46,820

Dan Maccarone: Best piece of advice

I've ever been given is, uh, it

00:56:46,820 --> 00:56:50,260

might sound silly, but it's, is

this the hill you want to die on?

00:56:50,910 --> 00:56:53,290

Meaning, what fights are you,

what fights do you feel are worth

00:56:53,330 --> 00:56:54,980

fighting, and what fights are not?

00:56:55,310 --> 00:57:00,550

Because we have them every single

day, and it's made me smarter

00:57:00,560 --> 00:57:02,529

about how I approach conversations.

00:57:02,970 --> 00:57:06,330

And where I will fight and I

will fight, um, for things and

00:57:06,330 --> 00:57:07,440

where it's like, you know what?

00:57:08,020 --> 00:57:09,800

Let's just let this, let's just go.

00:57:11,350 --> 00:57:13,800

Mike Gruen: Uh, what book

should every entrepreneur read?

00:57:14,780 --> 00:57:15,240

Mine.

00:57:19,290 --> 00:57:19,459

Dan Maccarone: Go

00:57:19,459 --> 00:57:21,069

Tim Winkler: ahead and plug it.

00:57:21,069 --> 00:57:21,860

Shameless plug.

00:57:21,880 --> 00:57:23,070

Dan Maccarone: I'll give you two actually.

00:57:23,110 --> 00:57:24,719

So my book is called The Marshall MBA.