CTO Wisdom with Barnaby Dorfman | Beyond the Program

Welcome to CTO Wisdom. In this series, we interview technical leaders who have stepped into executive positions.

Today’s guest host, Eric Brooke, speaks with Barnaby, Dorfman, a visionary technology executive with decades of leadership experience in the tech industry.

In today’s episode, they discuss:

• The importance of learning how to sell ideas in a way your audience understands
• How to lead through layers of abstraction
• The importance of considering the Product Lifecycle in the way you build the Team
• The toughest part of technical leadership
• And much more!

About today’s guest: Barnaby Dorfman is a visionary technology executive with decades of leadership experience in the tech industry. His career spans a broad spectrum of roles, including founding startups, leading innovative projects at Amazon.com, and driving growth as a CTO for several companies. He is currently supporting multiple CEOs with tech strategy and execution. His role at Go1 as CTO was marked by remarkable achievements in building a global team and securing investments from top-tier venture capital firms, contributing significantly to the eLearning platform's hyper-growth. Barnaby's tenure in technology leadership positions, such as his time at Payscale.com and his groundbreaking work at Amazon.com, reflects his passion for creating high-performance teams and innovative products. He is credited with launching the first version of Amazon Marketplace, developing IMDbPro.com, and inventing search technologies used globally. With a deep commitment to fostering a culture of innovation, collaboration, and excellence, Barnaby continues to influence the tech industry through his advisory roles and speaking engagements, sharing insights drawn from a rich and diverse career. Barnaby graduated magna cum laude from San Francisco State University and has an MBA from the Tuck School at Dartmouth.

About today’s host: Eric Brooke has a rich and varied leadership career - leading up to 21,000 people and Billions in revenue, throughout 14 countries. In their career, they have been an Executive six times (e.g. President, CEO, CMO, and CTO) and a Board member of multiple organisations. Eric has been a CTO of scaling startups from 0 to 120 engineers. As an adviser and mentor, they have helped multiple other startups scale both in Canada and the US. As well as supporting multiple startup incubators such as 1871 in Chicago and TechStars.

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Eric Brooke: Welcome to CTO Wisdom.

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My name is Eric Brooke.

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This series will talk to leaders

of technology at organizations.

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We'll understand their career, what

was successful and what was not and

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what they learned along the way.

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We'll also look at what the

tech market is doing today.

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We'll understand where they gather

their intelligence so they can grow

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and scale with their organizations.

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Hey, Barnaby, welcome to CTO wisdom.

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Barnaby Dorfman: Hi,

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Eric Brooke: great to be here.

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Um, could you give me the elevator

pitch of yourself, please?

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Barnaby Dorfman: Sure.

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I am a serial chief product

and technology officer.

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Been doing it for 25, 30 years.

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Um, grew up, sort of cut my teeth in

early Amazon, worked on, uh, everything

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from the first version of the Amazon

marketplace to, to core search technology,

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uh, recommendations, personalization,

and a few things in the middle.

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And then.

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Since then, I've spent just decades

in early stage startups and then

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more recently kind of, um, scale ups.

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So kind of going from 10, 20

million annual recurring revenue

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up into north of a hundred million.

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A lot of that in the HR space, HR

information, human resources, uh, but

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a lot of experience with media as well,

and really take an integrative approach

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between, uh, product design engineering

Uh, and then also just as a C suite

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executive, kind of the connection

between the tech org and the rest of the

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company is something that I've really

been leaning into in the latter years.

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Awesome.

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Eric Brooke: Could you tell us about

your journey to becoming an exec?

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So maybe go back to when you're a manager,

you choose which point you want to do.

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Um, what was that like?

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And what did you learn about

at that point of your career?

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Barnaby Dorfman: Sure.

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I mean, it's, it's a constant evolution

and in some ways be hard to pick a

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single point, but I guess I would say.

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I would, I would pick a couple of things.

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One, I went to business school, I have

an MBA, and I think that really creates a

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lot of the foundation for what you need.

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Uh, you know, people ask me frequently

today if they still think it's relevant.

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And I use things that I

learned in business school from

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decades ago on a daily basis.

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Um, so I think that's

a foundational piece.

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Uh, but you know, I think

again, back to my time.

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At, at, uh, I want, you know, I went

up at Amazon as part of an acquisition.

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I was essentially in the C suite of

a small startup that then went up at

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Amazon, but Amazon was very small.

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And I mean, I think there were maybe

200 people in corporate in Seattle

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at the time, most, if not the whole

time I was there about seven years,

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my managers reported to Jeff Bezos.

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So while I wasn't in the C suite as a C

level executive, I was physically present.

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So I kind of in the room

where it happens, if you will.

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Um, and I got to see.

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You know, incredibly smart people

figuring it out as they went, because

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they were also junior and doing it for

the first time, um, and in some ways

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kind of catch up to the industry and

in some ways go beyond and invent new

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things, you know, like some of the

things that are pretty famous about

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Amazon today, you know, it was amazing

to watch them unfold and unfurl.

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Um, that's, that's, that was kind of

a step function that I would say if

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I jumped forward, you know, was it a

number of smaller startups, um, where the

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difference between being an individual

contributor and, and, uh, you know, in

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a C level executive was not that great.

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Um, but then when I got into kind

of, again, the scale ups where we

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went from tens or a hundred people to

hundreds of people and tens or sub 10

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million in revenue to over a hundred

million, that's where I really learned.

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kind of what it takes to be that

connective tissue that, you know, becoming

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a, you know, a C level executive requires.

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Eric Brooke: Okay.

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So when you think about, um, your

management journey, what are some of

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the powerful things before you got to

C suite that you learned along the way?

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Barnaby Dorfman: You know, I think a

lot of it was around pitching my ideas.

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You know, one of the things I

love about software development

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is everything's possible.

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You know, the, the feasible

region, if you will, of what can

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be done is essentially infinite.

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But the problem with that is that, you

know, it's, if you're talking about,

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Oh, I want to build a bridge or I want

to build a building, you know, it's

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kind of the, the set of things that are

possible is much more limited by physics.

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And, you know, History of

architecture, things like that.

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But, uh, tech is so unlimited.

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And so one of the things I struggled

with early on was having these ideas and

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communicating them and basically selling

my ideas, selling myself and my ideas.

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And frankly, I think showing

up in a way that was, you know,

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emotionally intelligent and.

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You know, I think early on, even though

I was right about some things that turned

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out to be absolutely massive monster

businesses over time, I did not present

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that in a way in a way that helped other

people understand, sort it relative to all

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the other great ideas, because the whole

thing is just exploding in the early web.

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Um, so that, that was a, that's a

kind of a really important piece.

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Uh, you know, I mean, an example of that

would be again, the Amazon marketplace,

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which was very controversial internally.

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And.

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Yeah, you can understand why you have

an established business selling books

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and suddenly you want third parties

to sell books and treat your customers

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as well as you would and not mess up

your relationship with publishers.

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Um, But the way that we were going

about it, frankly, wasn't working

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because we had them separate and, um,

and again, I, I just got frustrated

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and I just like expected people

to see things the way I saw them.

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And it was, it's really been kind

of in growing and learning that,

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Hey, everybody's doing their best,

you know, almost all the time.

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All people are trying to do

their best work and the best

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thing for less themselves, but

their, their company, their team.

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Um, and if you can.

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Find ways of relating to them and

figuring out where their objections

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and they may just be right.

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It's the other thing you may be wrong.

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Your idea may not work, but I guess the

thumb it's really around being better at,

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um, also just using metrics and analytics

to present in a very objective way and

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then really getting into the shoes of the

person that I need to get buy in from,

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um, rather than just sort of wanting to

shake them and say, can't you see it?

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Eric Brooke: So, yeah, what I heard

was like, you went from here's the idea

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and people would, you get a resounding

silence to what are the people I'm

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trying to convince, who are they, what

do they want, what do they need, what

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convinces them, whether it be metrics and

improving that influencing capability.

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Barnaby Dorfman: Absolutely.

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Yeah.

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Good summary.

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Cool.

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Eric Brooke: Okay.

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So you've been, you've kind of like

building up this skill set, you're

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becoming a manager and then you

eventually get to managing of managers.

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Do you have any thoughts or

recommendations for people

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that are like getting to manage

managers for the first time?

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Barnaby Dorfman: That's a good question.

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People usually ask me about managing for

the first time, but managing managers,

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I think, I think it really is, you

know, you have to think you have to lead

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through more layers of abstraction, right?

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Like, you, you can't, you can't

influence people directly,

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especially as the org gets larger.

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If you're managing hundreds of,

you know, have an organization with

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hundreds of people and managers

and managers reporting into you.

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The, the ability to kind of stand

next to somebody and help them through

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a problem or, you know, work with

them directly basically goes away.

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There's just not enough

time in the day or the week.

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Um, so you really have to think

about how you can simplify.

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Even more, I mean, simplification is

always important, but I think that

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again, if I can stand there face

to face and explain my half baked

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idea and, you know, and how do you

ask questions till we get there?

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That's 1 way of working with

somebody as a manager or the inverse

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there and perfect ideas and you're

helping them get get it fully baked.

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But once you get into the

managing managers, I think

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that's the best way to go.

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Now communication becomes harder and

something you have to be much more

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thoughtful about and put more effort into.

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I like to say that the transparency,

which I believe is super important, is

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not the opposite of keeping secrets.

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Transparency, you know, requires effort.

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You have to work at it.

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You have to craft the message.

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You have to think about the delivery

mechanism, the timing, the audience.

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All of these things become

much, much more important.

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Everything around communication

becomes a much bigger issue.

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I think one of the advantages that,

um, people should lean into is

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now you actually have a portfolio.

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You're, you're essentially working

with a portfolio of talent versus,

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you know, a toolbox of talent.

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You know, I think, and if you think

about kind of investment theory, that

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diversification is, You know, almost

always a benefit, you know, in the

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stock portfolio, same thing with, with

a talent portfolio and how you think

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about how you balance that and you think

about the, um, the makeup of that talent

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pool and how well it meets the needs

of your organization, the strategy, the

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various stakeholders, there's, you know,

there's kind of this, um, much more.

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Zoomed out view that you have

to take and think about sort of

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how the pieces all fit together.

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Uh, and it'd be planning, you

know, thoughtful about that.

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I think, you know, one of for as an

example Having a strategy for hiring,

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you know, i've scaled Engineering

product tech teams from single digits,

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you know, into triple digits or,

you know, very fast growth at times.

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And, you know, we're depending

on where we are in the cycle.

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And I've made some terrible mistakes.

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Like, 1 of the ones that I've really

been leaning into, you know, now for

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quite some time is just, um, thinking

hard about the ratio of senior to junior.

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And at one company where we got a funding

round and, you know, we're expected to

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grow the team and do some acquisitions and

some integrations and just tons of growth.

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Um, I was strongly encouraged by a

variety of, uh, stakeholders that

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I should hire a bunch of senior.

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Particularly in engineering.

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And so I did that and they all

wanted the title of architect.

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So I had, you know, I had a friend of

an architect and a backend architect

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and a mid tier architect and a lunch

architect and like everybody was an

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architect and, you know, and then

eventually they just, they, they, they

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all thought, you know, like cats in a bag.

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I mean, it was, it was not

a good situation because.

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So often with technology, there

isn't a right architecture,

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more important than anything.

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It's everybody's agreed on and

following the patterns that,

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you know, have been set forth.

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And if you've got three or four or

five people who believe it's their

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job to define those patterns, you

wind up in a really bad place.

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And so I think, um, being very thoughtful

about that ratio of junior to senior.

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Uh, and always role

clarity is super important.

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It's important at all levels.

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But again, if you've got a larger

organization having good clean lines

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of separation of who owns what, where,

where's, where is the separation

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between two orgs or two teams,

because if there's a lot of overlap,

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you wind up with a lot of Problems.

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And if there's no overlap, you

wind up with a lot of problems.

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So you want, you know, kind of, you

want them sort of adjacent or, or

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touching shoulders, but not, um, you

know, trying to sit in the same chair.

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Eric Brooke: So you talked

about the ratio of, like, over

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employing in terms of senior, and

that having a lot of architects.

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So what do you actually

use as a basis now?

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Because obviously, the implicit of

what you're saying is that you should

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hire juniors as well as seniors.

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How do you think about that now?

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Barnaby Dorfman: It really depends

on what you're building, where

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you are in kind of the lifecycle

of the technology, the company.

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So if you're, you know, if you're earlier

stage or you're building completely

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new stuff, um, you know, that you're

going to need to start with some senior

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people who can design an architect.

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If you're just maintaining something,

you probably don't need an architect.

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You know, and there are everybody

always in this business wants

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to, you know, kind of be moving

quickly and changing and replacing.

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And sometimes it's just

not the right thing for the

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business or in the marketplace.

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Um, so if something is in

maintenance mode, uh, or,

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you know, some other kind of.

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Mode, say lots of integrations and

connections with third parties is

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another thing that I've experienced.

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You, again, you don't really need to

be building stuff, whole cloth and

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you don't need architects, but also if

you've got a lot of serious tech debt

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and or, um, a need to evolve a product

because of some technical innovation,

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I mean, artificial intelligence, large

language models, where, you know, Huge

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right now, and they are going to impact

a lot of business and businesses, and

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they are going to require reworking and

refactoring many, many, many applications.

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So those are some examples of places

where, again, I think you'd lean

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into some, some more senior folks.

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I will say also, you know, there are a

number of, for a number of reasons, I

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believe that more junior people are more

capable than they ever have been, and

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it's not, that's not a slight against more

senior people and their unique abilities.

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But I think the.

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The change, there's a few

things that have happened.

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One, the knowledge base that's available

online, you know, not in books, you

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know, those, remember those big, thick

Q books that, you know, we were expected

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to read, to learn how to use Excel.

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Yeah.

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Right behind you.

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It's sound installation now.

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Right.

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Um, and, um, and so that's

all available online.

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And now also with, you know, like

a chat GPT, you can actually.

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Sort of interrogate that knowledge

base in ways you never could before.

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So that's what's available from

a knowledge perspective has

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really come a long ways and

continues to, to, to accelerate.

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Then I would say also the tool set, right?

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Like the number of, um, I mean, low

code, no code cloud, you know, when a,

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when a new software development engineer

sits down at their desk for the first

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time, they are empowered with a master,

skill level set of tools on day one.

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Um, and that's also a change.

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And I think within that is also

some architectural processes things.

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So, you know, continuous employment,

continuous, um, you know, CICD, continuous

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integration, continuous deployment,

um, is something, and, and, and then

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also kind of like the ability to launch

things, Uh, you know, into a branch, um,

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on production, but, um, you know, behind

a feature flag so that it's internal

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users, only testers, and then do a canary

release where the, you know, the number

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of external users ramps from 0 to 1, you

know, not up to 100 percent means that.

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Whereas, say, 20 years ago, a new grad

out of software, uh, out of a software

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development engineering program,

computer science program, might be

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expected to spend months learning, you

know, the architecture and, uh, custom

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tools and language modifications and,

and the business before they check

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in any code that goes to production.

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Also, the development and

deployment cycles were much longer.

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Now, you know, I, I believe in a lot

of companies like, like Meta, I think,

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you know, you're expected to check

in code to production on day one.

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Um, and so all of that means that I

think you can, if you're thinking about

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that portfolio of talent I mentioned,

um, you can get a lot more done with

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more junior people than you used to.

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The ratios of like sort of straight out

of school, you know, Uh, 1 to say, you

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know, 3 or 5 years, 5 to 8 or 10, you

know, 10 to 15 and then more senior.

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I think the, um, you know, you can get

a lot more done with more people at

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the junior end than you could before.

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Eric Brooke: Yeah.

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And to add to that, and I think you

included this, there's so much better

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tooling that we don't have so much

complexity that we used to have.

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Um, And we don't need to create

everything custom, right?

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Okay.

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So, um, managing managers,

you talked about transparency.

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You talked about getting the right, um,

ratio of junior and seniors considering

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the context of the business and what

the business needs heard that all.

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Um, what else would you say is

important for helping managers?

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Um, managing managers?

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Barnaby Dorfman: I think it's the,

your role as connective tissue to

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other parts of your organization.

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And I, you know, I tend to think of these

things as con concentric circles, right?

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So one of the ways that I've des sort

of describe career progression to,

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to people, especially young people

outta school, is it's little bit like

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dropping a upon a pebble in a pond.

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You're the pebble and when the pebble

first drops, you know, there's that one

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little circle and that's, that's your

first year, you know, out of school and

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then over time, those rings go out and out

and out and by the time you're, you know,

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you're at the C suite, you've reached

the edges of the pond, all edges, right?

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Like, you're touching everything,

your wrinkles and your, your,

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the energy that you put out

reaches the whole organization.

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So.

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As you're in that, that journey,

think about kind of where you are.

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And so let's say you're a

new manager of managers.

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Um, you've got one, you know, one sort of

skip level below the, your direct reports.

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Um, and you're one of say five

direct reports to You know, a VP

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or a C level executive, or, you

know, sort of senior director.

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Um, you know, you need to really

think about how you help your teams.

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Um, assuming that each manager you

manage represents an individual team,

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how are they connecting with each other?

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What, you know, what mechanisms

have you created for them to be.

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Aligned, um, have transparency with each

other, uh, you know, hold each other

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accountable, celebrate each other's

successes, all of those things, then,

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and that's kind of your oversight

within the, your group of people that

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you manage, then there's, okay, now I,

as a manager of, you know, as a senior

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manager or maybe a director level,

um, how do I effectively connect with.

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My peers within, you know, the, the,

all the people that report to the,

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my manager, so that's, and that's, I

really liked the idea of the first team.

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Um, the author, Patrick Munchione,

uh, kind of, I think he introduced it.

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That's where I learned it.

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It's the notion that your first team

is not the people who report to you or

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the, in this case, the managers that you

manage, but it's actually the people.

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Your peers who report into your

manager and you're accountable, you

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know, that your success is dependent

on their success and vice versa.

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And so making sure that you have, you

know, really good collegial, hopefully

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friendship level relationships with those

folks, because that the alignment or lack

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thereof is what's going to determine.

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The success of, you know, your immediate

organization and your manager's success,

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the organization, you know, that success.

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And then I think you start thinking about,

um, you know, okay, where else in the

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organization do I need to be connecting?

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So, you know, I think like

relationships between tech org

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and, um, product marketing sales.

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support, sometimes legal, um, are

kind of notoriously not great.

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And I think that one of the things that

as people start to move up, they can

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have a very positive impact on, but

they can also learn for themselves is

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how do I effectively in a positive way

with as much emotional intelligence as

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I can engage with those other functions?

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So that, you know, let's say legal,

for example, you're going through GDPR

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issues or, you know, other, uh, maybe,

you know, contractual kinds of things.

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IT and security can be another

area of either friction or

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wonderful collaboration.

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Um, but like.

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Building a relationship, understanding,

you know, why the legal department has

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created, you know, whatever structures

that has, you know, why they think

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it's important that I do or not do

these things, um, and, and just really

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show up and be present to understand.

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Kind of things from their

perspective on the support side.

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I think that's an area that, uh, you know,

if you don't have a good relationship

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with the support org, you're not going to

have quality software in my experience.

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Like they're, they're the tip of

the spear of where, um, so many

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of the quality problems that are,

that our users, our customers are

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experiencing, um, comes in contact.

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And if we think about.

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For yourself, like how upset and

angry and frustrated you have to

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be before you file a ticket, right?

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Like, you'll like, most of us just because

it's so painful for so many organizations.

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So, by the time somebody's

actually filed the ticket, um.

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You know, they've already gotten to

a level of, of, you know, frustration

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and if the support org is saying, and

I'm getting a lot of these, or I'm,

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I'm having to do these workarounds

to help our customers or whatever, I

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think it's really important to really

listen to that and, and be extremely

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empathetic and try everything you can

to fully understand what the issue is.

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And not fall into the temptation of, oh,

you know, people just don't understand

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or don't know how to use it or whatever

it is, or you need to do a better job

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of explaining it and just think about

how can you incorporate that into.

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Your daily work, monthly work, you

know, your planning, et cetera.

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And again, finding that, that

balance, because one of the back

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to the point about in software,

the possibilities are endless.

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So are the demands, right?

376

Like, and so you leveraging, and I

think, well, I don't think I know

377

software development, engineers,

programmers, they like building high

378

quality software, they don't like bugs.

379

And one of, you know, you can, you

can, I've seen relationships go from.

380

Oh, we just, you know, the support org

just doesn't get it to, Oh, the support

381

org gives me the data that I need to

be able to then go work with my product

382

managers, my, you know, business, um,

you know, stakeholders, whoever it is

383

and say, Hey, I know that you think

that feature would be really cool.

384

Um, but we've got a, you know, a large

number of users who are actually trying to

385

use this feature we built that they want,

and they, you know, Like, but it doesn't

386

work correctly because there is a bug or

there's an exception or whatever it is.

387

I'm going to put time and resources

into fixing this or making this

388

better before I build that new

thing that you're excited about.

389

And, you know, there's a lot you can

talk about how to manage that, but.

390

Um, there's an interplay, I guess

is what I'm trying to say between

391

the, the interactions and the,

the data and anecdotes that you

392

get back from other organizations.

393

And I just chose support

as one to focus on.

394

But sales is another

mar marketing product.

395

Marketing is another finance, uh,

you know, living in your budget.

396

That, that's another one that I

think is like just deer in headlights

397

for a lot of first time managers.

398

Managers in particular where

now you're actually allocating.

399

Things like dollars between, you

know, teams and people in, in a much

400

more, um, expansive and dynamic way.

401

Uh, and so, you know, your partnership

with, with finance can become a really

402

important part of, of your role.

403

Eric Brooke: So setting up a community

for your peers is an important thing.

404

So you can learn from each other,

give each other feedback, um, and

405

also expanding beyond technology into

the other departments to understand.

406

One, what are they doing?

407

Why are they doing it?

408

Building empathy for them.

409

And then also building stronger

relationships is the kind of things.

410

And customer success is like, obviously

the one that you primarily use.

411

And I 100 percent agree with you.

412

They are the best bug hunters because

your consumers are finding things.

413

So that's great.

414

So, and also the first team mentality.

415

So moving to the, your first team moves.

416

So you're now in the exec.

417

How, what was that transition like

for you, if you can remember it and

418

what are the important things to

think about when you're in the VP role

419

before you've got to the CTO role?

420

Barnaby Dorfman: Yeah, I,

I, a bunch of failures.

421

You know, uh, ranging from just, again,

not doing a good job of building bridges.

422

And, you know, I, I, there's a thing

that happens a lot in tech, which is that

423

tech tech builds up technology moves on.

424

And I think the human instinct is you sort

of out with the old and with the new and

425

like, let's, let's, you know, let's just

bring cleaning and we're going to do,

426

you know, we're going to go from V1 to V2

and that also used to be how software was

427

built right when we had to put, put it on

to disk and mail it out to people you had

428

multi year development cycles because you.

429

You know, you couldn't test, you

didn't know what people were doing

430

or how they were using it, and you

couldn't fix bugs, uh, you know, once

431

they went out, so you just really

had to go, you know, slow and steady.

432

The web is just not like that.

433

Um, but the, I think kind of this, this

notion that it's time to just rip and

434

replace is something that I've, I've

embraced and failed at several times.

435

I've resisted and failed in being

effective at communicating the why and.

436

So, I think that, I'm thinking about

it as an example of places where I

437

had conflict or lack of alignment

with other people within, you know, or

438

other VPs, um, and, you know, either

didn't succeed in what I was doing

439

or caused general failure to spread.

440

Um, and, and it really just,

again, comes down to relationships.

441

I think, um, Yeah, just being really,

really thoughtful about my interpersonal

442

relationships and, you know, in some

ways I'm repeating kind of what it

443

was as I went from, but it just, it

just gets more important as you go.

444

And, uh, I'm trying to think of other

things that sort of definitively change.

445

Well, your time horizons change a lot.

446

I guess that's something I

didn't I haven't mentioned yet.

447

I think that, you know, you tend to.

448

You're an individual contributor.

449

You know, you're, you're heads down

focused on what I'm doing today.

450

And, you know, kind of what's expected

of me, you know, the sprint, um, you

451

know, and I'm probably curious about

the company strategy, you know, what's

452

going on and stuff, but, you know, I

don't really pay that much attention

453

unless there's a really healthy, well

developed OKR quarterly kind of system.

454

But most of my day to day is like focused

on the here and now, and then as you

455

move up, you know, you maybe you're,

you're thinking, you know, you're,

456

you're responsible for if you're, if

you've really leaned into agile, uh,

457

two experience, you know, you're, you're

sort of, that's, you know, like the last

458

sprint and, and sort of this sprint, and

maybe you're thinking about next sprint.

459

Right.

460

So that's kind of a six

week spread, if you will.

461

Um, yeah.

462

I think that, you know, then once you

become kind of a VP level, you tend to

463

think about like quarterly OKRs, quarterly

QBRs, quarterly business reviews, um,

464

and then, you know, once you get into

the, to the C suite, um, or, or kind

465

of go further, then now you tend to

think about, you know, there's an annual

466

planning cycle that you spend months on,

um, there's, you know, kind of mid year

467

review and, you know, there's an annual,

um, Planning, um, budgeting, you know, the

468

budget planning becomes that frame that

you work inside of, um, and then you also

469

tend to worry about things, you know, at a

strategic level out, you know, 3 5 years,

470

um, hopefully you're in an organization

that does that kind of thoughtful stuff.

471

At least every couple of years is

kind of, you know, I think people tend

472

to work with a strategy too often.

473

Uh, don't give enough time to execute,

which tends to lead to a little

474

too much, um, context switching.

475

Uh, but a thoughtful balance of

really long term, you know, where

476

is this company going to be?

477

You know, in 20 years, um, if, if, you

know, if that's, if that's an appropriate

478

frame, it doesn't always, but you know,

somebody like that was something that

479

I definitely learned from Jeff Bezos,

you know, and he's pretty famous slash

480

infamous for that long term thinking.

481

Um, but.

482

Yeah, those time horizons expand.

483

And in that time you spend thinking

about working on, um, producing

484

work product, you know, analytics,

frameworks, documents, presentations,

485

um, that spreads over a longer period.

486

And it's more forward looking,

uh, is a big, big piece of it.

487

I think also, Yeah.

488

Metrics, you know, if you're just if

you're building software, you maybe

489

you're maybe you're responsible for,

you know, some dashboards and monitoring

490

services or those kinds of things.

491

But typically, you're, you're not

looking at a larger, broader dashboard

492

and the connectivity again between, um.

493

You know, unit sales or, or, um,

subscriptions and things like churn and

494

average revenue per user and, uh, customer

acquisition costs and, uh, hosting costs,

495

the cost of goods, you know, everything

that goes into cost of goods sold.

496

Cost of, of, uh, headcount, the

biggest, you know, the biggest

497

chunk of all the budgets that I've

managed, you know, in C, CPCTO roles.

498

Um, you know, and then again, the

connectivity that to profitability

499

and then typically, you know,

whether it's a startup or a PE backed

500

company, and I've been in both.

501

You do have some sort of a horizon,

you know, uh, uh, event, an exit,

502

a sale that you're thinking about.

503

And, and you may be actively working

on that, or you just may be like,

504

we just got acquired by a PE.

505

And so we know their average hold

period is four or five years.

506

So, you know, they're going to

come in and there's going to

507

be an immediate action plan.

508

And then there's going to be a

series of years of execution.

509

And then we're going to get it ready

for sale where you are in that cycle.

510

But again, these longer time horizons,

there's a few examples of how that can

511

work that I think becomes part of your

day to day as you get more senior.

512

Eric Brooke: So, when you think

about it, Barnaby, what does

513

success look like for you?

514

And what has helped you be successful?

515

Barnaby Dorfman: You know, I think

for me, uh, you know, I mean, I'm

516

not economically rational, rational.

517

I'm economically rational,

so I care about money.

518

Um, but You know, i've also realized

that If you spend a lot of time thinking

519

about it or worrying about it, you're

probably not actually going to be

520

successful in making a lot of money.

521

And most, most of the really wealthy

people that I know don't spend a whole

522

lot of time thinking about, you know,

what it takes to make money or how they

523

made the money or how to make more money.

524

Um, they think about how to

create value in the world.

525

And so for me, you know, whereas money

and title maybe were more important to

526

me now, it's really, am I creating value?

527

Um, and am I creating value on

probably two primary vectors?

528

One is it just for customers in the

world, I'm highly customer centric.

529

And so am I building, improving, creating,

maintaining, whatever it is, a product

530

solution that large numbers of people.

531

You know, find valuable impacts

their lives in positive ways,

532

reduces some pain somehow, um, makes

things easier for them, helps them

533

cut costs or be more successful.

534

The other vector is how well am I doing

internally in terms of, um, having,

535

You know, happy, healthy employees

who are in themselves being successful

536

in whatever, however, they define it,

whatever their goals are, their growth,

537

um, you know, the fundamentals of the

Maslow's hierarchy stuff of, can I

538

feed myself and take care of my family?

539

Um, and then, you know, up into self

actualization of like, you know, that

540

classic thing that a lot of engineers

hit, which I really love coding, but I've

541

been at it for, you know, 12 years and

I'm getting asked to, you know, manage a

542

team and I'm not sure if I want to, and

how can I, you know, and, and, and so

543

I'm at that fork in the road and, um, you

know, how can I help them through that?

544

Uh, which can be, you know, scary and

lead to people leaving companies because

545

of, you know, that can be handled

poorly, or it can lead to, you know,

546

I've had, you know, I've seen people

step into leadership who were kind

547

of resistant to it and didn't think

it was for them and they've blossomed

548

and been incredibly successful at it.

549

I've seen people who you would think

because of their personality, you

550

know, they seem, you know, sort

of outgoing, gregarious, whatever.

551

Turns out, no, you know what their

best uses is, you know, Sitting

552

at a keyboard most of the day.

553

Um, coding.

554

Uh, and I've seen, I've seen hybrids and

I've seen people, but I've, I've also seen

555

people leave companies because of how that

transition was handled or how the need to

556

go back the other direction was handled.

557

Uh, so that's a little bit of a deep

dive into my definition of success

558

is, is really the success of my,

Organization and, and, and, and again,

559

like I said earlier, not just the people

in the report up in the mirror in my,

560

in my immediate, um, team, but also,

you know, if, if engineering is doing

561

great, but sales can't sell anything,

or they're not hitting their quotas.

562

It doesn't, you know, it doesn't work.

563

So it's, it's how, how well is the

collective doing and what's helped you be

564

Eric Brooke: successful?

565

Barnaby Dorfman: Well, I would say

mistakes and failure and learning

566

from them that, you know, that's

always really, really important.

567

I think curiosity, just be curious.

568

And if you don't know the answer to

something, maybe also being a little

569

bit impatient to get an answer.

570

And sometimes that's just a Google

search, but sometimes there is no answer.

571

Nobody's ever thought of the question.

572

Um, because nobody's been in the

situation you're in, uh, having been,

573

you know, Working in internet powered

technologies since a really long time,

574

the, uh, in my life, but a very short

period and, you know, in the span of

575

human history, um, there's just, uh,

you know, I've been lucky to be on,

576

you know, kind of out of the front

of the frontier of so many things.

577

And so, so often.

578

There is no answer.

579

The only way to get an answer is to do an

experiment and explore and try, try new

580

things that nobody's ever done before.

581

Um, so I think back to the

question of what makes me

582

successful is I seek that out.

583

You know, if somebody

tells me, Hey, go do this.

584

And I'm like, that's,

that's a solved problem.

585

Like, you know, There are lots and

lots of people who've done that

586

probably done it better than me.

587

I'm not going to gravitate towards that.

588

I'm going to gravitate more towards the

thing that is like, nobody's ever done it

589

probably isn't going to work, but if it

does, you know, you can change the world.

590

Um, and that's part of

that curiosity thing.

591

Um, I think a few other things that come

to mind are really, really focusing on,

592

on sort of the human side of things.

593

I just, I think a lot of engineers.

594

Consider themselves to be highly

analytical and that they make

595

decisions based on data and facts.

596

They also tend to be more introverted

than extroverted sort of on the

597

spectrum on on that spectrum.

598

They tend to, you know, sort

of turn towards that side.

599

And what I, what I've seen is that that

can lead to somebody who thinks that they

600

are a non emotional creature, um, And,

and then they sort of deny their feelings

601

about a thing about, Hey, that reorg was

the fifth this year, and I don't even

602

understand why I'm building what I'm

building, or, you know, they just, they

603

just promoted this guy's been sitting

next to me for two months, you know, just

604

joined the company two months ago, and

I've been here for two years and I have

605

more experience and I don't understand it.

606

And, you know, whatever it is.

607

And, and I think as a result, they

can often bottle up some, some of the

608

emotions and feelings about, um, how

things are going and then, and then it

609

can explode in a, in a nonproductive way.

610

So, you know, being really, really

thoughtful about the people.

611

And I think, listen, I have this

sort of working hypothesis right

612

now that, um, we've, we've.

613

As an industry created so many of

the building blocks, foundational

614

technologies, ways of working, uh,

infrastructure, you know, we, we

615

can rely on high speed, you know,

ubiquitously available bandwidth

616

pretty much anywhere on the planet.

617

Now, um, we don't have to buy expensive

software to build software, the open

618

source, you know, operating systems and

frameworks, you know, cloud computer.

619

We don't have to, I have to rack them.

620

Hardware have people get up in the middle

of the night to switch out hard drives.

621

I mean, I can keep going, I think,

you know, mobile and now the gen AI is

622

kind of that next step function of, of

building blocks and yet based on, you

623

know, despite all of that, most, most

applications, most web applications,

624

mobile applications are mediocre at best.

625

And, and there's some good ones that

drag up the average, you know, sort of

626

mainly the big tech companies, not that

they don't still have their usability

627

problems, but you get to the average,

um, bank, airline, government, school,

628

hospital website, and it can be almost

impossible to get basic stuff done.

629

Uh, and why is that?

630

Well, the why is it still requires

human beings to be aligned.

631

Um, focused on the customer heading

in the same direction with agreed

632

upon ways of working and executing,

and that's still really hard.

633

And so back to the question of why

am I successful is I've put a lot

634

of time into focusing on how, how

to help a team, um, really do the

635

thing, you know, those things have

that customer focus and, and, and, you

636

know, it'd be a whole nother series

of podcasts, really probably to share.

637

A lot of the little things that

I've learned through trial and error

638

and, you know, adopted from other

people that make the difference.

639

And I do think it's also worth noting

that so much of what is, um, traditional.

640

Instinctual, uh, and intuitive does

not work when it comes to software

641

development and the web and usability

and design and those kinds of things.

642

And so, if you just rely on sort

of human intuition, that's why a

643

lot of these websites don't work.

644

That

645

Eric Brooke: a lot of people

have cognitive biases that they

646

don't know how to manage them.

647

Like categorization, we love to

categorize things, label things,

648

and that's not always helpful.

649

Um, and actually can cause more problems.

650

So thank you for that.

651

Um, so thinking about what are you

seeing in the wider tech market today?

652

Barnaby Dorfman: I think there are a

number of things that are worth noting.

653

Uh, I, I, I mean, I think, so

obviously Gen AI, super hot topic.

654

I think that it is.

655

In a place that's similar to, you know,

like what happened, let's say with

656

cloud computing, um, whatever, however

long, 15, 20 years ago that really

657

started, uh, where the hype exceeded

the reality for some initial period.

658

And then there was a little bit of

a like, Hey, you know what marketers

659

are just putting that name on

something that's not really a cloud.

660

There's nothing cloud

about that, whatever.

661

Um, this is, you know, a lot of

people concluded wrongly that,

662

that it really was just fluff.

663

In the long run, cloud truly

represented a step function in

664

the way that we, um, do our work.

665

And I would say that the long term

impact has exceeded the initial hype.

666

I think that where we're at right now,

I mean, Chet GPT is 14 months old.

667

Um, The hype last year

was, you know, massive.

668

The hype now is massive, but I'm

starting to see people like, Oh, it's

669

not really that big a deal or whatever.

670

And, you know, and, and we have yet to

see the killer app beyond chat GPT, right?

671

Like in terms of something that's really,

really changing the world, I think

672

we're going to see some killer apps by

before the end of this calendar year.

673

Um, and I, I think it's going to

be, you know, in a variety of areas,

674

but for example, customer service

and, and chatbots replacing the

675

Madlibs chatbots with something that.

676

Actually could be better than humans,

um, because you've trained it on all

677

of your, your, your documentation,

your actual code, every single support

678

ticket you've ever had, um, that, that

chat bot powered by an LLM is going to

679

do better than somebody who had, you

know, maybe a few days of training,

680

you know, in a culture different

than where the user is, et cetera.

681

Um, so that's, that's something I'm

excited about, like lots of people, but

682

that's her buying out my, my thought.

683

Those are my thoughts

on where that thing is.

684

I think the others were

in an interesting place.

685

You know, there were obviously

a lot of layoffs last year.

686

We've seen, I think a lot of people

thought, okay, that's over, but then

687

we've seen a bunch more this year.

688

Some of it tied to a transition

from kind of shutting down things

689

that weren't actually working.

690

I mean, you just think about like

how big Alexa, you know, the, the,

691

the Alexa team was at Amazon, but you

know, and the equivalent, you know,

692

at Google and Siri at Apple, it just

completely missed the boat and did not.

693

You know, get it done relative to

what the LLMs are capable of doing.

694

So there's thousands of people who

were toiling away on things that were

695

pointing in the right, wrong direction.

696

Um, and I think, you know, we

also, we had, I mean, I've been

697

through enough recessions that I

remember the dot com bubble burst,

698

you know, very, very vividly.

699

And that was a long, low slog back.

700

And then the Great Recession,

again, Pretty long, slow slog back.

701

And then we didn't really have

any sort of a correction as an

702

industry, um, or an economy.

703

Um, you know, since say 2012 ish, up

until kind of last year, and these,

704

you know, these things were companies

would just hire massive teams to prevent

705

competitors from getting them and

then they'd have them doing work that

706

was of questionable internal value.

707

Um, so I think this correction was needed.

708

Ultimately will be healthy, but

it's also led to a lot of froth,

709

a lot of froth in the marketplace.

710

I, you know, I, I, um, I currently

am, uh, you know, kind of doing some

711

advisory work and, and kind of part-time

fractional C-P-T-O-C-T-O type jobs.

712

So I'm talking to a lot of people and

I, you know, I, I company after company,

713

I see, you know, they're on LinkedIn,

you know, premium, they've got the

714

insights graph, and, you know, the, the

hiring curve is basically an inverted v.

715

Over and over and over again.

716

I see, you know, it's it went from 200

to 400 down to 250 or some version of

717

that, you know, whatever scale and, um,

you know, I talked to a CEO recently who,

718

uh, you know, product that I've used, um,

they, uh, raised a bunch of money kind of

719

in that during the pandemic, uh, sort of.

720

Everything's shifting to online.

721

Everything's got to be

automated more so than before.

722

And just this displacement caused

money to flow in new directions.

723

And so this company was the

benefactor of that raised.

724

It's lots of money, got a unicorn

status valuation, uh, and the CEO is

725

like, I spent 80 million, you know,

dollars on, uh, you know, basically

726

development, you know, over a period.

727

And I have essentially

nothing to show for it.

728

Uh, can you come help me figure

out why and how I fix it?

729

And I think there's a lot of

that out there and just general

730

kind of froth, um, around it.

731

Thanks.

732

Do you know, do I, what kinds of people

do I need, um, what are the market

733

opportunities with gen AI and how do I

adapt to the sort of new environment?

734

And again, trends are trends, right?

735

Like the trend, you know, there, there

I've been in, I've been in a board

736

meeting where an investor said, I just

invested a huge amount of money and

737

it's not for you to earn interest.

738

Well, at the time interest

rates were basically zero and

739

everything was about growth.

740

I guarantee you that same investors like

I want to see your layoff plan, uh, you

741

know, if you don't need to spend it, you

know, you can get 5 percent on your money.

742

Um, so, you know, you got to sort

of play with what is happening

743

in the environment today.

744

And so those are some of the

dynamics that we're dealing with.

745

And as interest rates come down, um.

746

That will change the dynamics of

investment and the funding environment.

747

That's, I guess, that's another piece

that I would mention is that a lot of

748

folks are made around is fully keyed

into is when, you know, when interest

749

rates are essentially zero, high net

worth individuals, um, retirement

750

funds, sovereign funds from governments,

et cetera, um, they pour their money

751

into private equity, even though

private equity, you know, the top end,

752

you know, 20, 30 percent of Um, you

know, the middle tier is going to be

753

10, 12 and the bottom quartile, you

know, it can be 5 percent or below.

754

And so with when you can get five

or six or even higher percent risk

755

free without also the long term

commitment, because those funds, you

756

know, you're getting in that for 5, 10

plus years, five quick 10, 10 years.

757

Um, The risk reward ratio is out of whack.

758

And so much of what we all live

on in the tech industry is the

759

flow of investment from VC and PE.

760

But I think, you know, because inflation

is moderated, you know, so many people

761

are counting on betting on is interest

rates will come down this year, long

762

term rates have already come down.

763

Um, and then, you know, the investment

flow will, the spigot will open up again.

764

Um, so that's another piece I would

say that I'm seeing out there.

765

Cool.

766

Hopefulness.

767

Eric Brooke: That's great to hear.

768

Um, Barnaby, thank you.

769

My last question for you

is what do you do for fun?

770

Barnaby Dorfman: I had a long

list of things I do for fun.

771

I love to cook.

772

Um, I've always been into food, uh,

born and raised in New York City.

773

And, you know, sort of my family

really embraced the multicultural,

774

uh, culinary aspects of the city.

775

And I've.

776

Traveled and lived in a

bunch of parts of the world.

777

And I, I, I like to say that, um, cooking

is the only perfect art form because it

778

is the only art form that uses all of the

human senses of, you know, taste, sight,

779

sound, even the crunch, um, obviously the

smell, uh, you know, all of that matters.

780

Uh, so I just, and it's infinite, right?

781

There's always something

new to try to learn.

782

Uh, and, um, It is a great way

of connecting with people and,

783

uh, spending time and learning.

784

And it's a little bit also, I think

because we eat every day and multiple

785

times a day as humans, typically,

um, it's kind of like the ability.

786

One of the things I love about working

on the web is the ability to do, to

787

run experiments, AB tests, right.

788

If you've got enough traffic, you know,

you think it should be around, but I

789

think it should be a square button.

790

Let's just, you know, let's AB test it.

791

And whoever's right is right.

792

Well, you know, in my family, you know, I.

793

Try addition and everybody hates it.

794

Maybe not going to do it again.

795

Or maybe everybody's like, well,

just lay off the garlic or, you know,

796

whatever it is, like, try it again.

797

Oh, everybody loves it.

798

It's got that same sort of.

799

Opportunity for

experimentation and learning.

800

Uh, that's multi sort of

multidimensional that I enjoy.

801

Eric Brooke: Awesome.

802

Barnaby, thank you very much for your

time today and the wisdom and all

803

of the journey that you've shared.

804

Deeply appreciate

805

Barnaby Dorfman: it.

806

Thank you.

807

Thank you.

808

My pleasure.

809

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