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The One Person You Need to Scale Your Business with Jen Goldman (stage 3) - Ep. 334
Episode 3347th October 2025 • The Start, Scale & Succeed Podcast • Scott Ritzheimer
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In this feasible episode, Jen Goldman, Founder of My Virtual COO, shares operational strategies for scaling teams. If you struggle with team frustration or management overload, you won't want to miss it.

You will discover:

- Why hiring aligned talent prevents management headaches in stage 3

- How to implement lean processes for efficient scaling

- How to implement lean processes for efficient scaling

This episode is ideal for for Founders, Owners, and CEOs in stage 3 of The Founder's Evolution. Not sure which stage you're in? Find out for free in less than 10 minutes at https://www.scalearchitects.com/founders/quiz

Jen Goldman brings 30 years of experience as a Business Transformist for Small Businesses. She has transformed hundreds and trained thousands of service businesses on how to scale up teams, profits, and clients through operational, skill, and mindset improvements. Jen’s expertise includes strategic business planning, staff and provider recalibration, change acceleration, tech integration optimization, Lean® process creation, and implementation and high adoption of operational efficiencies. Her philosophy includes Visualization, Productive Collaboration, 4W and 4Ps Purpose Documentation, and IDEOS ™.

Want to learn more about Jen Goldman's work at My Virtual COO? Check out her website at https://myvirtualcoo.com/

Mentioned in this episode:

Take the Founder's Evolution Quiz Today

If you’re a Founder, business owner, or CEO who feels overworked by the business you lead and underwhelmed by the results, you’re doing it wrong. Succeeding as a founder all comes down to doing the right one or two things right now. Take the quiz today at foundersquiz.com, and in just ten questions, you can figure out what stage you are in, so you can focus on what is going to work and say goodbye to everything else.

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Transcripts

Scott Ritzheimer:

Hello, hello and welcome. Welcome once again

Scott Ritzheimer:

to the start, scale and succeed podcast, the only podcast that

Scott Ritzheimer:

grows with you through all seven stages of your journey. As a

Scott Ritzheimer:

founder, I'm your host, Scott Ritzheimer, and this episode is

Scott Ritzheimer:

for all you reluctant managers out there, you know who you are.

Scott Ritzheimer:

I just actually had a call with a small business owner who was

Scott Ritzheimer:

ready to throw it all away. She was done. And like, with a

Scott Ritzheimer:

capital D, and she was so frustrated with the team that

Scott Ritzheimer:

she'd built. There were about 20 people at this point. They just

Scott Ritzheimer:

added several more, and that was the tipping point. And to be

Scott Ritzheimer:

honest, like they were super frustrated with her. And so she

Scott Ritzheimer:

had just had enough, and was asking for advice on how to

Scott Ritzheimer:

sell, because in a moment of, you know, just genuine honesty,

Scott Ritzheimer:

she shared that she was she had given up hope that it could get

Scott Ritzheimer:

any better than it currently was. And if you felt that way,

Scott Ritzheimer:

if you feel that way, it can get a whole lot better. In fact,

Scott Ritzheimer:

most folks who are in this position are just a couple turns

Scott Ritzheimer:

of the dial, and we're going to talk about one of those

Scott Ritzheimer:

important ones in this episode, from just a completely different

Scott Ritzheimer:

experience, completely different growth, and a whole lot of fun

Scott Ritzheimer:

and that with a capital F and so here to help us have a little

Scott Ritzheimer:

more hope, and for all the right reasons, is Jen Goldman, who

Scott Ritzheimer:

brings 30 years of experience as a business transformation. A

Scott Ritzheimer:

transformist for small businesses, she has helped

Scott Ritzheimer:

hundreds and 1000s of service businesses to learn how to scale

Scott Ritzheimer:

up teams, profit and clients through operational skill and

Scott Ritzheimer:

mindset improvements. Jen's experience includes strategic

Scott Ritzheimer:

business planning staff and provider recalibration, change,

Scott Ritzheimer:

acceleration, tech integration and optimization, lean process

Scott Ritzheimer:

creation and implementation and high adoption of operational

Scott Ritzheimer:

efficiencies. Her philosophy includes visualization, product

Scott Ritzheimer:

collaboration, the 4w and four P's, purpose documentation and

Scott Ritzheimer:

IDEO. She's here with us today. Jen, welcome to the show. Very

Scott Ritzheimer:

excited to have you on. A question for you coming out of

Scott Ritzheimer:

the gate here is, what would you say to the founder like her,

Scott Ritzheimer:

who's waking up pretty much every morning wondering what's

Scott Ritzheimer:

wrong with these people? How can a COO help?

Jen Goldman:

Yeah. So first off, I hear you certainly, I'm a

Jen Goldman:

business owner too, so I'm smiling with you, and I'm

Jen Goldman:

feeling the pain. Secondly, to be perfect, there's a middle

Jen Goldman:

person missing off the team, and so just to be as transparent as

Jen Goldman:

possible, I think what you're missing is that COO or Chief of

Jen Goldman:

Staff, and there is a slight difference between the two, but

Jen Goldman:

we're going to blend them together today.

Scott Ritzheimer:

Yeah, I'm so glad you brought that up, and I

Scott Ritzheimer:

actually do want to separate those just momentarily, and then

Scott Ritzheimer:

we'll lump them together, because it was actually a

Scott Ritzheimer:

question that I had, and I didn't know if we'd be able to

Scott Ritzheimer:

get into it. But what do you mean by that? Because most folks

Scott Ritzheimer:

probably haven't had either. So in you as short as you can, I

Scott Ritzheimer:

know that's a lofty ambition, but what's the Chief of Staff?

Scott Ritzheimer:

How's that different than a COO?

Jen Goldman:

Yeah, so a chief of staff is going to come in very

Jen Goldman:

people oriented, bringing the team together, aligning and kind

Jen Goldman:

of sit between you, the CEO, biz dev, and the team's day to day

Jen Goldman:

operations. Okay, so, but they're going to lead with

Jen Goldman:

people. A COO is going to lead with operational efficiencies.

Jen Goldman:

So they're going to be a little more tech geeky. They're going

Jen Goldman:

to be a little bit more into processes that kind of guide the

Jen Goldman:

people they care about, the people, don't get me wrong, but

Jen Goldman:

their their first and highest calling is more around systems

Jen Goldman:

than it is around people.

Scott Ritzheimer:

Right, how do you know which one you need?

Jen Goldman:

That's a great question. I think if you think

Jen Goldman:

the culture is lacking, like, let's say you have turnover or

Jen Goldman:

low retention, or everybody seems a little basically fried

Jen Goldman:

out, I would say you need a Chief of Staff first, or

Jen Goldman:

somebody that will put that first and then kind of come in

Jen Goldman:

the unicorn. This is what everybody wants. I want it,

Jen Goldman:

right? You want the Chief of Staff and the COO in one person,

Jen Goldman:

yeah? So you can try for that if you want. But I would say again,

Jen Goldman:

if culture is dragging, mood is dragging, everybody's just

Jen Goldman:

struggling, bring in the Chief of Staff first, then bring in

Jen Goldman:

like a COO mentality, or hopefully groom up from somebody

Jen Goldman:

on the team.

Scott Ritzheimer:

Yeah, so let's talk a little bit about what

Scott Ritzheimer:

this COO role does. You talked about operational efficiency.

Scott Ritzheimer:

How does that role, that second in command in a COO mindset,

Scott Ritzheimer:

help a founder to scale? How's it different from what the

Scott Ritzheimer:

founder is doing themselves?

Jen Goldman:

Well, first of all, they're the day to day, so the

Jen Goldman:

founder gets to be especially if you're a biz dev founder, which

Jen Goldman:

you understand you know more than anyone, right? If you're a

Jen Goldman:

biz dev founder, and you get your energy from relationship

Jen Goldman:

building outside of the office, outside of the company, with new

Jen Goldman:

leads or referral sources, right then that COO is the one that

Jen Goldman:

does in the office. They're the one that runs the team meetings.

Jen Goldman:

They're the one that looks for ways to cut down on the workload

Jen Goldman:

so your team can stay lean and not. Mean, but happy. And so

Jen Goldman:

basically, as a COO, you're freed, like once they're

Jen Goldman:

onboarded and ingrained, you're free to go out and do your thing

Jen Goldman:

and bring out your vibe and sell and let the COO deal with the

Jen Goldman:

day to day.

Scott Ritzheimer:

Yeah, one of the things that I've found, and

Scott Ritzheimer:

I'd probably venture to say it's the most important thing you

Scott Ritzheimer:

might push back on that. I'd be interested in your thoughts. But

Scott Ritzheimer:

it seems to me that the biggest contributor to success is trust

Scott Ritzheimer:

in the relationship between COO and CEO. You could have an

Scott Ritzheimer:

unreal COO, it's just a Jedi at all the process. But if you

Scott Ritzheimer:

don't trust them, you're going to go in and undermine every

Scott Ritzheimer:

last one of them. So I'd love to know from you, what do you see

Scott Ritzheimer:

as the role of trust, and how do you start to build that from

Scott Ritzheimer:

even before day one in an interview process?

Jen Goldman:

Yeah, I'm a very big proponent of documentation.

Jen Goldman:

So if you met any one of my quote, business friends, or even

Jen Goldman:

our clients, they would understand trust comes not only

Jen Goldman:

with the verbal but the written. So for example, you asked about

Jen Goldman:

even before hiring, how do they cross communicate

Jen Goldman:

asynchronously? Are they clear? Are they understandable? Do they

Jen Goldman:

respond in a timely manner? All that matters in an interview

Jen Goldman:

process, I don't know. I look at it, I care about it, because

Jen Goldman:

that's how they're going to be when they're working with you,

Jen Goldman:

hopefully, right? And and if they're poor in the interview

Jen Goldman:

process, let me tell you, they're not going to fit, right?

Jen Goldman:

We know that automatically, because you get better, not get

Jen Goldman:

better, that's right. So things like that when they're on

Jen Goldman:

boarded trust weekly meetings. Do they come prepared? Is there

Jen Goldman:

a set agenda? Are they documenting what they're doing?

Jen Goldman:

And I think also too, let me flip this the person that's

Jen Goldman:

documenting that gives you dopamine hits, it makes you feel

Jen Goldman:

jazzed up, and it gives you a list of saying, Hey, this is

Jen Goldman:

what I just accomplished for the business. So there's a win on

Jen Goldman:

both sides. It's not supposed to be a drag, right? That builds up

Jen Goldman:

a ton of trust, another thing. And actually, somebody did this

Jen Goldman:

to me. My wing man in the past, actually would write an end of

Jen Goldman:

the week summary and say, These are the top five things I

Jen Goldman:

accomplish. Obviously, she was getting the dopamine hit writing

Jen Goldman:

it, but I automatically went into the weekend and a mindset

Jen Goldman:

of this person is on it, and they care, and they're doing the

Jen Goldman:

work.

Scott Ritzheimer:

That's so powerful, because it's the

Scott Ritzheimer:

weekends where we go crazy. Yeah, it's like, Monday morning.

Scott Ritzheimer:

I have some interesting calls, you know, and I get it, you

Scott Ritzheimer:

know, because it's you, you have a little time, you get into a

Scott Ritzheimer:

project, you kind of start poking around and stuff, and

Scott Ritzheimer:

then, boom, your whole weekend's gone because you just went down

Scott Ritzheimer:

19 rabbit trolls, of of what feels like awful. And so to be

Scott Ritzheimer:

able to just set that up and say, Hey, we're good, right?

Scott Ritzheimer:

Going into the weekend, we're good, it'll all be here. Monday

Scott Ritzheimer:

will be okay, is, I mean, from a life impact standpoint, it's

Scott Ritzheimer:

massive for founders.

Jen Goldman:

No, I mean, that's we don't get our energy in those

Jen Goldman:

moments, whether it's weekends or nights. We're not good

Jen Goldman:

leaders, whether they're whatever direction we're heading

Jen Goldman:

in. And that's where you get the owners that say, I'm out, like

Jen Goldman:

I'm just done, like I'm burnt. And the reason they're they're

Jen Goldman:

burning themselves out because they don't have, to be frank,

Jen Goldman:

the systems in place, and they don't, and it's okay because you

Jen Goldman:

don't know, like, this is stuff that I took for granted, and

Jen Goldman:

then I realized most people don't know this, but that also

Jen Goldman:

burns out the team. So then you're wondering, why, why are

Jen Goldman:

these people on my team, and why are they not, like, kicking it

Jen Goldman:

up, and you haven't given them a method or a way to communicate

Jen Goldman:

up the ladder or to take credit and advocate. Yeah, yeah. So

Jen Goldman:

systems matter in that in that instance.

Scott Ritzheimer:

And I love the way that you describe systems,

Scott Ritzheimer:

because most founders wouldn't describe them that way. They

Scott Ritzheimer:

describe it as like, prison. You know, go back and listen to it

Scott Ritzheimer:

again. It's just fantastic. There's a lot in there. I want

Scott Ritzheimer:

to kind of stay on this thread with CEOs, though. So let's say

Scott Ritzheimer:

someone's like, Yes, that's what we need. We need someone to

Scott Ritzheimer:

bring some more structure to this thing. I'd love to have

Scott Ritzheimer:

someone looking inside my business so I can look out on

Scott Ritzheimer:

the horizon and create some growth. What do they need to

Scott Ritzheimer:

look for in a great COO, what are some of the qualities that

Scott Ritzheimer:

you've seen make those folks successful?

Jen Goldman:

I'm going to give the answer, but I know the

Jen Goldman:

follow up question would be, well, Jen, what question would

Jen Goldman:

you ask in an interview? So let me give the answer first. It's

Jen Goldman:

called, I call it constellation thinking. So we believe in this

Jen Goldman:

thing called the four Ps. And I made that up for myself, just to

Jen Goldman:

be fair. And now I teach it that when we think of anything in a

Jen Goldman:

business, we think about, how is it going to affect the people,

Jen Goldman:

the productivity, the profits and the presence, internally and

Jen Goldman:

externally. Okay, so public presence and internal presence.

Jen Goldman:

So that's constellation thinking automatically that everything

Jen Goldman:

you do has an impact and has a trickle effect. You need to see.

Jen Goldman:

See that in that person. So you need to give them an instance or

Jen Goldman:

a story and say, What did you take away from that story? And

Jen Goldman:

they see if they connect the dots between all the areas of

Jen Goldman:

the business and the impact of what was going on, yeah, you

Jen Goldman:

need that. You need to know they can articulate it, right? I'm

Jen Goldman:

trying to think what else you can ask them, but I do think

Jen Goldman:

it's going think it's constellation. Thinking you're

Jen Goldman:

looking for that. You're looking for an eagerness to learn. They

Jen Goldman:

really have to be learning junkies. So and how they learn,

Jen Goldman:

that's a big one. If they learn verbally, that's going to slow

Jen Goldman:

you down, because the fact is, you don't have the time you're

Jen Goldman:

busy on your calls or talking to clients, or for whatever you're

Jen Goldman:

doing, CEO out there, leading, presenting, it doesn't whatever

Jen Goldman:

your business is. You have to make sure they can learn without

Jen Goldman:

the verbal Yeah. So it might be on their own, through video, on

Jen Goldman:

their own, through written word, on their own, through some other

Jen Goldman:

way. Are they resourceful? I think that's another, another

Jen Goldman:

big one.

Scott Ritzheimer:

This idea of constellation thinking is is

Scott Ritzheimer:

really profound, because as you look back at like, who are the

Scott Ritzheimer:

hires that precede this? You don't really hire them for that,

Scott Ritzheimer:

right? You might hire them for one, maybe two of these, but

Scott Ritzheimer:

it's like you're you the first handful of folks you hire for

Scott Ritzheimer:

them to get stuff done and and to some extent, the less they're

Scott Ritzheimer:

worried about all the connection points, the more efficient or

Scott Ritzheimer:

effective they'll be in their particular role. But then that

Scott Ritzheimer:

leaves you like doing the juggling number, you know, and

Scott Ritzheimer:

trying to hang it all together. And so where I've seen folks

Scott Ritzheimer:

struggle here is that they don't apply that switch, right? They

Scott Ritzheimer:

try and bring in somebody else to solve what they think is a

Scott Ritzheimer:

single problem. I need someone to connect me in the team, or

Scott Ritzheimer:

something like that, and it's missing that constellation

Scott Ritzheimer:

thinking. That's very, very clever way of putting it, but

Scott Ritzheimer:

very, very important. So there's another thread to this that I'm

Scott Ritzheimer:

very interested in hearing what you have to say, and that is,

Scott Ritzheimer:

how do you figure out the the full time in person, virtual How

Scott Ritzheimer:

do you know what's right for you in terms of how much coo you

Scott Ritzheimer:

need and in what format?

Jen Goldman:

Yeah, that's a great question. I would say most

Jen Goldman:

of the time. I'll get let me give a real example. So we were

Jen Goldman:

talking to a business that was sent to us through a connection

Jen Goldman:

at strategic coach. And they were probably, I'm thinking,

Jen Goldman:

looking down to think about maybe 1819, people on the team,

Jen Goldman:

two owners, right? One was like the head of sales. One was

Jen Goldman:

operations, and they were maxed out the story like you started

Jen Goldman:

with, just by showing them all the different pieces. And we

Jen Goldman:

show visuals, by the way, we're huge individuals around people

Jen Goldman:

and systems and everything. We literally have a map for each

Jen Goldman:

item the minute. We actually showed them that, in probably

Jen Goldman:

under five minutes, they were like, Whoa. I didn't realize I

Jen Goldman:

was thinking that way. No wonder my brain hurts trying to figure

Jen Goldman:

this all out and make it better for the next scale up, we need a

Jen Goldman:

full timer. They instantly knew that, because when they saw it,

Jen Goldman:

they're like, I want that. So I think you don't know. Well, you

Jen Goldman:

don't know Right? Like, you just know you're burning out, right?

Jen Goldman:

Or you just you're tired of everything. That's one thing. If

Jen Goldman:

you think that you want to touch on your people and your systems

Jen Goldman:

and your processes, and, God, there's so much to go your

Jen Goldman:

finances, like I want to project my profitability through all

Jen Goldman:

this. Then I think you need a full timer. Then the question

Jen Goldman:

is, do you do virtual or in house? Well, first of all,

Jen Goldman:

depends on your company model. I'm going to tell you virtual

Jen Goldman:

works with a quarterly visit in house, because, frankly, a lot

Jen Goldman:

can get done, and you can get better talent, maybe not in your

Jen Goldman:

backyard. And also budget matters, right? Like, maybe

Jen Goldman:

you're in I'm in the Northeast. Let me tell you what people like

Jen Goldman:

this make, right? They make a lot. Maybe you can't afford

Jen Goldman:

that. So I would say to do the virtual and have them visit you

Jen Goldman:

quarterly type of thing. If they're good communicators this

Jen Goldman:

way, like we're even communicating and in written

Jen Goldman:

it's not a problem. Yeah, it's your problem,

Scott Ritzheimer:

And it's it's so much better than just sitting

Scott Ritzheimer:

and waiting you, because really it's like, even if you don't

Scott Ritzheimer:

think that virtual is ideal with the end, with the tools, and not

Scott Ritzheimer:

just like zoom, but like the organizational tools that are

Scott Ritzheimer:

available to us. Now, it's remarkable what you can do

Scott Ritzheimer:

virtually. But on top of that, even if it were an intermediary

Scott Ritzheimer:

step toward a full time in person, whatever that might look

Scott Ritzheimer:

like, it's going to rapidly accelerate that process for you.

Scott Ritzheimer:

Would you agree?

Jen Goldman:

Absolutely, I say to businesses, if you want to

Jen Goldman:

continue to grow healthy. You need this role. You need it.

Jen Goldman:

Otherwise you're going to burn out, you're going to miss and

Jen Goldman:

make costly missteps, or you're going to stagnate the growth. I

Jen Goldman:

can't tell you. This will pain you more than you know how many

Jen Goldman:

businesses come and I'm starting to see them flat line. It's not

Jen Goldman:

that maybe the revenues are down, but they're just not. To

Jen Goldman:

uptick, and that's a bad you're already on the you're already in

Jen Goldman:

a bad place. And so I just don't think, I think businesses I care

Jen Goldman:

to make an impact and help more, whatever that is, whether it's

Jen Goldman:

other businesses, individuals, I don't really care. But if you

Jen Goldman:

want that, this is the role you need. So the difference between

Jen Goldman:

hiring full time or doing a fractional I'd say, Listen, that

Jen Goldman:

comes down to how you feel, what your budget is, and if you want

Jen Goldman:

to dip your toe in, but dip your toe and I'm not, you know, and

Jen Goldman:

people say, Oh, I'm self serving, because this is what I

Jen Goldman:

do. I really, honestly, I really don't I love for people to reach

Jen Goldman:

out to us. I'd love for people to reach out to anybody that's a

Jen Goldman:

COO and do this, because when you do, you hear the great

Jen Goldman:

stories, and you then you become the great story of success.

Scott Ritzheimer:

What, Yeah, what a way. So I want to end on

Scott Ritzheimer:

that note, but I've got one more question for you, and that is,

Scott Ritzheimer:

what is the biggest secret that you wish wasn't a secret at all?

Scott Ritzheimer:

What's that one thing you wish everybody watching or listening

Scott Ritzheimer:

today knew?

Jen Goldman:

The one that came to mind is something you would

Jen Goldman:

say, and not me, but I'll say it because I live in it. No, no,

Jen Goldman:

no. Saying no is crucial, even when you're a startup and you

Jen Goldman:

need that extra client, or you like that person you wanna add

Jen Goldman:

them to the team? You gotta I think we all need to trust our

Jen Goldman:

gut a little bit more and say no, because I think what happens

Jen Goldman:

is we dilute the business and our own personal health. So if I

Jen Goldman:

would leave it on that secret no is important right at the

Jen Goldman:

beginning.

Scott Ritzheimer:

Oh, it's so important. It's so scary,

Scott Ritzheimer:

especially early on. It's terrifying, but it's terrifying

Scott Ritzheimer:

for all of us. And there's just a you're saying no, whether you

Scott Ritzheimer:

want to or not. It's just a question of whether you're doing

Scott Ritzheimer:

it or it's happening to you. So take the initiative and do it.

Scott Ritzheimer:

Jen, we could go on for a really long time and help a whole lot

Scott Ritzheimer:

of people doing it, I'm sure, but they can get a lot of help

Scott Ritzheimer:

by reaching out to you directly. How can folks find more out

Scott Ritzheimer:

about the work that you do and connect with you?

Jen Goldman:

Yeah, if you just want to go to My Virtual COO,

Jen Goldman:

we're there. We've got some freebies. Feel free to jump on

Jen Goldman:

and then you can reach out to us if you want.

Scott Ritzheimer:

Fantastic, myvirtualcoo.com We'll get it in

Scott Ritzheimer:

the show notes for you so you don't have to go find it. Jen,

Scott Ritzheimer:

thanks for being on today. What a fun conversation. It's a

Scott Ritzheimer:

privilege and honor having you here for those of you who are

Scott Ritzheimer:

watching and listening, you know your time and attention mean the

Scott Ritzheimer:

world to us. I hope you got as much out of this conversation as

Scott Ritzheimer:

I know I did, and I cannot wait to see you next time. Take care.

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