CTO Wisdom with Joel Schlundt | 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 Joel Schlundt, CTO at TextUs, a business texting software.

In today’s episode, they discuss some of the key learnings from Joel’s career journey to becoming a CTO:

• Giving your managers room and space to take risks and be there to support them as they need it
• Creating empathy between you and your other partners throughout the business, to create strong business value
• Being a force multiplier for all parts of the business not just Engineering and Product
• Balancing the needs of product delivery, platform, and people

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 organizations. 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,

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and 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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Welcome to Joel, who we'll

be chatting with today.

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Hey, Joe, would you like to

introduce yourself, please?

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Joel Schlundt: Thanks Eric.

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I'm Joel Schlundt.

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I'm the CTO at TextUs.

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Um, we're a There's this SMS platform

that specializes in conversational

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as well as campaign based messaging.

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Awesome.

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Eric Brooke: Joel, could you tell

me a little about your journey to

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becoming an executive in technology?

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Sure.

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Joel Schlundt: Um, I've always

had technology around in my life.

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Um, I've had a father who was an

early adopter, so, you know, we always

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had the newest technology, whether

that was, uh, Or a personal computer

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in the house at a very early age.

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I was always encouraged to explore

and I think that just really founded a

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natural curiosity around technology and.

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Um, a lot of things in that space and

from there, um, you know, I was given

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the opportunity to participate in.

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In programming camps and in

other software related, uh.

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Activities that, um, really

kind of fostered this, this

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love of technology starting even

as early as elementary school.

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And from there, um, just really

went on to, uh, a more traditional

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computer science education, and then,

uh, started my development career.

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Um, and through that, uh, experience.

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Um, I've had the opportunity to do

a lot of different types of things.

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Um.

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And whenever opportunities arise, I

always volunteered, um, again, just I

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have a real natural curiosity around.

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Uh, technology and in different

types of platforms or or systems.

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And so that gave me a really

interesting, interesting perspective

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and experiences that I might not have

normally been able to have otherwise.

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So now I have I done software development,

but I've worked on more system

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implementations system integrations.

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Through these different experiences, I've

been able to, um, really learn what I'm

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more, more passionate about in, in what I,

what I excel at and also the areas that,

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um, aren't as, as interesting or, or,

uh, fulfilling for me, which has really

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helped me kind of guide my career as well.

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Eric Brooke: I'm interested,

you talked about that you had

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a computer in the early days.

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Um, can you remember what

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Joel Schlundt: it was?

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Yes, so, um, our first computer at

the house was a Commodore VIC 20.

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Oh.

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Uh, and then from there, we, uh,

moved to an Apple II, um, and then

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had a Commodore Amiga, and then,

uh, eventually an IBM PC clone.

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Eric Brooke: Okay.

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And you mentioned in that you like to jump

into things that you didn't necessarily

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know or understand, like, how did that

help you progress in terms of your career?

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Sure.

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Joel Schlundt: Sure.

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So, I think You know, very early on in

my career, even at my 1st job, we had a

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systems administrator for our work group.

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And, um, what was really interesting

is that a lot of the development.

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Team didn't interface or

interact with them very often.

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That didn't make a lot of sense to me.

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I mean, we had to work closely in concert

with with 1 another, but there was like

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this natural or or almost a barrier.

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Uh, in between the groups, and

I just was curious about what

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they did and how they did it.

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And, um, what work.

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Uh, looked like for them, and that gave

me a much better understanding of of

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what they were trying to accomplish,

how they're supporting our team.

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What it looked like to support

kind of a work group of our size

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and some of the challenges that.

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That they would run into on a regular

basis, I think that just gave me a

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great, a greater sense of empathy.

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For for the work that they do in open

up, you know, more information in

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in, um, different technologies that

I had never seen or been exposed to.

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Yeah,

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Eric Brooke: knowing the stack and

being having no fear of the stack.

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I definitely say is a good mark of a

good engineer when you kind of like.

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Um, when was the 1st time

you started doing management?

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Joel Schlundt: So I started

to, um, take on more software

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architecture responsibilities.

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Um, you know, at a point in my

career, and that really kind of led

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me down this path to to management.

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I had to start coordinating

and collaborating across.

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A large number of different

technology teams had to have a much

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better understanding of of business

requirements in in what we were

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trying to deliver for the business.

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And that that sort of work was

really energizing for me and really,

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um, kind of put me on that path.

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And from there, I started to take

on engineering team responsibilities

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and started to run in and lead

engineering teams and then started to

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get responsibility for other groups,

um, like QA and databases and, uh,

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DBAs, um, and then systems, um, And

since was administrators and so on,

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Eric Brooke: how was that transition for

you from say, an individual contributor

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as a software engineer to management?

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Was it easy?

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Was it hard?

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Joel Schlundt: It wasn't something

that I ever expected to do.

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Um, it wasn't something that

I, I planned or set out.

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What I found was interesting is,

um, I really enjoyed the people

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side of, of the, of that work.

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And I take a lot of satisfaction

in helping others succeed

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and grow professionally.

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And that was something that I,

I really didn't understand kind

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of before getting into this.

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As much, um, you know, there, there's

always a drawback to, you know,

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hands on keyboard kind of work.

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Um, there's ways that that.

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That desire to be more

directly involved or or.

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Closer to the technology, but I found

that I, I've been able to balance that

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with, you know, a lot of the other

things that that come with this job.

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The people side, the scaling

challenges, be able to have a

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greater purview over the business.

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I think, um, make up for some of

those, um, times where I'm not as

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close to the tech as, as I used to be.

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Eric Brooke: And so then you went

from management management and

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eventually you were managing managers.

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How

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Joel Schlundt: was that?

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Um, that scaling was challenging.

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Um, and I think like as you progress and

get higher, I think those, those types

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of challenges where you're learning how

to delegate in And distribute work more

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appropriately are hard to do, um, and,

you know, take time and in more energy

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than I think a lot of people realize and.

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You know, when done well, it, it

feels really, really, really good.

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And when it's challenging, you know,

it's sometimes hard to diagnose,

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especially when, when groups are

getting really, really large.

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Yeah.

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Um,

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Eric Brooke: are there any bits

of wisdom that you can talk about?

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Cause obviously you said

it was a little harder.

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So were there things when you, uh,

kind of more in that managing managers

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that you didn't know at the beginning

and then you felt, and then you

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started to find your way with it.

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Sure,

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Joel Schlundt: I think the, the big

learning for me was you have to give

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people room in, in space to take risks,

um, and, and make their own decisions.

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Um, you can help guide them, but

the more that they can decide

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and work independently, the,

the better off you both will be.

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And that was hard for me.

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You know, I'm sure there are a number

of cases, a number of occasions

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when I was more of a manager than

I would have ever wanted to be.

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And in those situations, you know,

the, the team doesn't move as fast

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or as successfully as they could.

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And, um, you know, the, the other

thing about being able to take

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risks is, is again, making sure that

they understand that you, you are

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supporting them all the way through.

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And if mistakes are made, we'll deal with

those in a reasonable and logical way.

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And, um, when something bad does

happen that you will have their back

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and get them through that situation.

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And typically people will learn a

lot more going through those, those

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types of mistakes, um, and end up in

a much better place long term anyway.

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Um, and it's hard because you need

a real sense of trust, you know,

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with your managers, um, and you

have to be willing to let go and and

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see mistakes happen along the way.

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And that's hard, and it's not always

pleasant and there are going to be some.

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Awkward situations or difficult

situations that you're faced with.

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Um, and and that's, you know, really, um,

what I found to be the most successful

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for me is, is again that that strong

support system and be able to give

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them independence in in some decent

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Eric Brooke: guidance.

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Yeah, Joe, I would agree.

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It is hard that part of the journey is

probably 1 of their real shifts away,

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but there's definitely a shift from.

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Um, individual contributors and

engineer to managing people.

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But that next one to like managing

managers is hard, but it gives

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you many more opportunities, as

you say, getting business value,

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being able to influence the team.

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Um, and then watching people grow

is a beautiful thing as well.

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Like they've got this, this is awesome.

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Cool.

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Okay.

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So the next step, um, from like your

managing managers and now you're an

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executive, how was that journey for you?

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Joel Schlundt: It was an interesting one.

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Um, again, it was one of

those situations where.

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It seemed like a very

natural progression, but

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it wasn't necessarily something

that, that I was planning for.

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Um, and the, the thing that I've,

I've liked most about, about that

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is again, being able to have a

wider purview, um, and to be able

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to learn more about, you know, how a

business is structured, how it runs.

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You know, what are, are more

effective ways to do things.

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And then just, I really liked

the sense of partnership, you

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know, with other business teams.

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Um, I, I, I really feel like

technology is an enabler.

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Um, I, I am a big believer in, in not

doing technology for technology sake.

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And it's like, how can we provide, you

know, value and be a force multiplier for.

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All the other business teams that we're

interacting with and, um, you know, that

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that moved to more of an executive level,

you know, really gave me that that kind

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of experience and was able to to really

teach me a lot about, um, those business

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areas and really develop those, those

type of relationships and partnerships

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with the other business teams.

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Eric Brooke: That's awesome.

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Were there kind of skills that you had

to learn at that stage of the job beyond

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like the business domain and obviously

what the other teams are doing and other

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departments, were there other skills that

going back in time, this would have been

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really good to have all kind of like build

up, as I would say, like a director of

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Joel Schlundt: sure.

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Um, I wish I would have known more about,

um, budgeting and In budget cycles, um,

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that has come up in in is something that

I, I deal with on on such a regular basis.

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I would have wish I would have

had more knowledge around how that

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works and typically works in in

different kind of business scenarios.

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I've seen it done a bunch of different

ways and in there are reasons for those

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different ways, but I wish I would

have known and understood that better.

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Um, you know, public company

reporting versus private venture

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backed versus private equity.

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You know, those, there are all kinds of

different scenarios that you run into.

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Um, but understanding kind of how

all that works and it ties together

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really leads to a lot of other

things from a business perspective.

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Yeah, absolutely.

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Eric Brooke: I think finance

is really helpful to know.

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Joel Schlundt: It drives a lot of

decision making, and the more you

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know about it, the better you are.

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Um, the other thing is just really

understanding communication styles

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and, um, understanding how to

communicate at that level and more

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strategically versus tactically.

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Um, that was another kind of big

shift that I saw in, in moving from.

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You know, very minute details, which

like engineering is all about to more

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strategic views and be able to talk more

directionally was something else that I,

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I wish I would have understood more and

better in getting into this because that's

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super important, especially when you're

trying to justify some decisions or help

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push push the team in a new direction.

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Yeah,

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Eric Brooke: absolutely.

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I think I learned a lot myself from

like sales teams, um, about how to sell,

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to be honest, and learned a lot from

marketing teams about how to show the

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return on investment along with product.

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Um, I agree.

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So what does success look like for you

and what has helped you be successful?

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Joel Schlundt: Um, success for me, like

I said, is, is really having technology

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be a partner to the rest of the business.

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Um, and, and that partnership

is really important.

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The, the things that that really

facilitate that is having a high level

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of empathy for, for those other groups.

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Like, you mentioned sales, being

able to actually go through a

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sales demo and see where the

platform shines where it doesn't.

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Understanding the struggles they

go through in, in, um, kind of.

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Addressing those sales objections,

um, and, you know, I think that's

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important for for technology

groups to really understand.

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And I think it again

just makes them better.

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Um, same goes for, like,

customer experience.

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Understanding, like, what your

customers are going through,

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how they're using the product.

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Um, what their what their

day to day use looks like.

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Is is so absolutely

important in and again.

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You want to build and deliver

the best quality price you can

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without having that understanding.

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I don't see that how that's possible.

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And what I found, too, is

engineers want to do a good job.

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In general, and they want to make

sure that they're delivering value.

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And the more insight you can give them

into how your customers are using it, or

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how the team has to support it, or how

sales has to sell it goes a long way.

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And typically they have.

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A lot of great ideas to help

make all of that better.

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Um, it's just enabling them to, to have

that voice and to gain that empathy.

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Um, and when those teams

have that empathy, I think I,

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I've seen the most success.

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The other thing, too, is balancing.

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The needs of the business versus the

needs of the, the team and to make sure

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that we're pairing up opportunities

for individual and professional

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growth as we're, we're building

product or, or delivering features.

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And, you know, there's often

a lot more flexibility.

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That you have in being able to

craft experiences for for your

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team to to experience that growth.

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Um, then you realize, and I've, I've been.

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Um, very fortunate that we've,

you know, through the course

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of my career have been able to.

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Um, a lot of folks in ways that were.

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Very specific to them and allow

them to either get into new areas

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of technology or or new focuses or.

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Um, you know, complete career

switches and and do that in a way

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that was positive for everybody.

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Like, there was a positive outcome.

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And I think that's that's super

important to me to, um, success is not

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just delivering the future on time.

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It's also delivering it in a way that.

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That the team can grow in,

in, in develop as well,

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Eric Brooke: um, in terms of like

success, like, obviously, at the exact

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level, we also get pressure around,

like, how is the team performing?

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Um, we often hear particularly

recently in the last year, a

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lot about productivity, um.

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What is you?

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How do you balance?

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Because you've talked a lot about

empathy, and you've also rightly

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said there's a balance between

the team and the business needs.

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How do you find balancing the pressure

that comes from, whether it be from the

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board, the CEO, sales, marketing, with

what your team is capable of delivering?

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Joel Schlundt: That I think is

one of the biggest challenges.

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Um, and, and, and problems to solve, you

know, in this, in this type of position.

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Um, and, and I think it

really is around balance.

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Um, you can't just focus on product

delivery, um, without worrying

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about the platform or the people.

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Um, because eventually you will fail,

and I think most people understand that

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deep down, but super willing to admit it.

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Um, and I think, you know, what has

helped me, you know, in these types

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of areas is just to be able to have

frank conversations and really explain.

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You know, why we have to balance and why

we have to spend time in other areas.

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And make sure that that is understood

sometimes it takes a number of

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conversations to make that happen.

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Sometimes we have to approach

it in different ways.

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You know, being able to

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find and strike that balance of

work, I think is really the key.

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Um, what has also helped is understanding.

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And to be able to understand again, like.

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The finances of the business, the

pressures that sales are under.

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Understanding kind of what the sales goals

look like, um, how we're supporting this,

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how we're marketing it so that you can

fit into those natural cycles that those

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other groups have and understanding that,

um, helps really tie the technology work

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more closely to the rest of the business.

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And again, you know, really helps with

that, that overall partnership as well.

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Yeah, I love what you

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Eric Brooke: said about the cycles because

each part of the department has different

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cycles they have to worry about, even

whether it's the people team and the end

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of the year or the finance at the end

of the month, like, yeah, absolutely.

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You need to have a good understanding

of your partners in the exec.

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Okay.

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So what is something that you're

trying to figure out at this moment?

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Joel Schlundt: Just like you

said, uh, the, um, problem around

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striking that balance, you know,

we're, we're a very ambitious team.

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We have lots, lots that we'd

like to get accomplished.

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We do have limited resources.

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How do we maximize the return on our

investment in terms of, of, of money

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and people, and, um, that's tough.

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You know, we, we, we want to

maximize developer productivity

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that requires investment.

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Which is going to delay features,

which potentially could could help

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fund, you know, additional resourcing.

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So, you know, we're working through

kind of finding the right balance

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for the team in, in making sure that.

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Our engineering team is as

productive as it can be.

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And we're delivering what we need

to and still keeping the platform.

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I'm stable and operational

for our customers and that's.

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That's tough.

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Um.

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The other kind of thing that, um, has been

top of mind is, is working on, you know,

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building and scaling the team and dealing

with some of the diversity issues in tech

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that, that we, you know, commonly see.

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Um, and, you know, this has been

something that, that I've thought

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about and worked on for a long time.

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Um, there's a lot of kind of systemic

issues just in technology with.

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With the type of people it attracts

and is able to to keep inside of

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tech, um, versus being able to

bring more, um, more diversity.

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And I've also learned that it's,

it's really more a more holistic

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picture of of how businesses run and

how they can attract non traditional

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candidates to these types of roles.

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You know, whether that's like,

flexibility in terms of of working

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hours and in location or better

benefits for family and medical leave.

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Um, maternity and paternity leaves all

of those things play a huge part in that.

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In order to, to really make a

difference in terms of diversity in

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engineering, um, hiring, you really

have to think about the bigger picture

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and in all of those things together.

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Yeah, um,

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Eric Brooke: I think engineering

obviously is interesting at the moment

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because we're going through big changes

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chat ttbt for, um, and people are

interested in see how much this, um.

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Predicting of the next word, um, will

actually really help and obviously

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it does great at summarization.

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So I feel like we're in for a big

shift, um, over the next few years,

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which I think will be interesting, may

open up opportunities for diversity

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in a way that it didn't exist before.

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But I also agree with you, it

should be a goal for all of us.

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Okay.

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Um, what is your

interaction with the exec?

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What does that look like?

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Could you give us like an example of what

it's like an exec to work with other exec?

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Joel Schlundt: Sure.

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So the, I keep using the word partnership.

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I really like that.

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Um, I like to have partners across

the table, um, that I'm working with.

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Um, and not for, um, I don't think you

can be successful if, if you're in an

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order taking or a role, um, it really has

to be an equal and equal conversation.

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And I've been super fortunate

that I've, I've been able

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to work with a lot of great.

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Um, peers and, you know, the, the

thing that I, I, I find really

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interesting, you know, folks that,

that are willing to share and, and

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let you into more of their space.

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And give you more information

about what they're doing,

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what they're struggling with.

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I think it's been, um, super enlightening

to me and really helpful in understanding

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ways I can help or, or just even be

more empathetic or, or, um, helping

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in, in more strategic ways in, in

terms of like longer term roadmap

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planning or, or technology initiatives.

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And, and the other thing too, is, um,

You know, at this level, we have to be

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pretty, um, candid with one another.

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Um, there are usually lots of really

difficult decisions that have to be

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made in, in, um, in those situations,

you really want to be able to, to have

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a high level of trust and to be able

to, to put everything out on the table.

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And that was not something that that I

completely expected or really understood

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coming up, but the better executive

teams and better groups really have

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a candor that that is special in in

can really make a huge difference.

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Um, and, you know, when you don't have

that, it can be a more toxic environment.

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And much more difficult

to get things done.

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Yeah,

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Eric Brooke: I agree with you, like,

the candidness is very important,

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and the ability to give each other

feedback and not take it personally.

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Because often you're giving feedback, not

just about the person, but sometimes the

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department and people in the department.

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Um, but partnership, absolutely.

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I love it when you hear them talking about

either the thing that they've discovered

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or the thing they're trying to solve.

416

And like, as engineers, our

core kind of like skill sets,

417

problem solving in the end.

418

And I don't think that ever goes

away, regardless of what level you

419

need, um, and being very open minded

to understanding of a trade that you

420

don't know as well as your partner.

421

Um, but yes.

422

Okay.

423

So what about the

interaction with the board?

424

How does that feel different?

425

And what kind of experiences do you have

426

Joel Schlundt: around that?

427

In dealing with a board, I've, I've

seen and heard horror stories around

428

very adversarial relationships or,

or, um, very misguided relationships.

429

I've had really good

experiences in, you know.

430

Being held accountable and in

really, um, questions around how

431

and why we're doing things, but

also in a very constructive way.

432

I think that the best boards

really will push, push you to think

433

harder and different about the

problems that you're faced with.

434

Um, and also provide just such a level

of experience that, that, you know,

435

if, if you're seeing a problem, they

most likely have had an experience

436

with it or, or something similar.

437

Um, or no people that have and can

help direct you to those, those

438

folks to, and it's really being

able to use them as a resource.

439

And, and, you know, there's just a lot

of learning that typically goes on, um,

440

in the board interactions that I've had.

441

Um, which has been great, um,

and super, super helpful for.

442

For not only me, and my function,

but but the business in general.

443

Awesome.

444

Eric Brooke: Yeah, I feel bored.

445

They ask questions a lot about finance

and how the return investment relates,

446

and it's an amazing growth opportunity.

447

Um, both the technical and non technical.

448

Um, I've certainly also seen them

being very helpful in recruitment.

449

Um, so they are, um, a different

environment, but something worthy

450

learning about and supporting.

451

Okay.

452

What are you seeing in the

wider tech market these days?

453

Joel Schlundt: Um, like we've

talked about, um, I think A.

454

I.

455

N.

456

G.

457

B.

458

T.

459

And and kind of advancements

that have been made over

460

such a short period of time.

461

I think it's really, really interesting

what software engineering looks like, you

462

know, even next year could be dramatically

different than what we're seeing today.

463

And I think that's exciting

and a little bit worrisome.

464

Um, just because it's not clear

how all of this will play out.

465

I do think it does have this interesting

effect in terms of being able to to

466

make like software development and

and even technology more accessible

467

to many more people, which I'm all

for and, you know, I think the other

468

thing, you know, just from a, from a.

469

Tech market perspective, you

know, we have a lot of very

470

cyclical, um, things in technology.

471

Um, we, we tend to repeat, um,

on a pretty frequent basis.

472

And, and, you know, I think we're,

we're kind of at the next cycle in

473

terms of understanding where front

end development is going to go.

474

Um, is that going to kind of

continue on its current course

475

or make kind of a radical shift?

476

You know, we're starting to see just the

starts of folks moving away from cloud

477

based hosting to more self hosting again,

which again, I think is an interesting

478

scenario and may have some merits, you

know, in very particular situations.

479

But I think we're going through again

another one of these change cycles where

480

we're going to see a lot of different,

uh, different ways to think about how

481

we deploy applications again and how

we think about front end development

482

and web development in general.

483

I mean, I think that's going

to be interesting over the

484

next, you know, 24 to, uh.

485

36 months.

486

Thank you.

487

Eric Brooke: What helped you grow

or helps you grow and scale now?

488

Like, what are the things that help you,

whether it be books, podcast mentors?

489

What are the things that

are helping you scale

490

Joel Schlundt: and grow?

491

Sure.

492

I, I try to listen and consume

as much content as I can.

493

Um, so I, I don't have a particular

podcast in mind, but I, I

494

listened to a lot of them and

I try to try to look for again.

495

Opinions or views from, from folks that,

that are in different spaces than my own.

496

Um, so either really, really large

organizations or, or startups in different

497

markets, those types of situations.

498

Um, I've also had a number of mentors

that have been super helpful, like

499

to me, you know, over the course

of my career and just understanding

500

management in general and, and,

and how to deal with team structure

501

and organization change management.

502

Um, and.

503

They have been instrumental in helping

kind of set that set that groundwork

504

up and being able to talk with kind of

ongoing and I try to listen to everybody

505

that I can, um, you know, whenever there's

an opportunity, like, again, I, I really

506

like to see what people are thinking and

how people how different people are going

507

through these same sorts of challenges.

508

And I just really try to keep

my ears open as much as I can.

509

Awesome.

510

Eric Brooke: Thanks, Joe.

511

Joel Schlundt: What do you do for fun?

512

Sure.

513

So, um, I have 3 daughters

and, um, they're, they are, um.

514

With my wife, what we spend a lot of

our free time doing spending time with

515

them participating in their activities.

516

We've gone through marching band and

lacrosse and now we're into debate.

517

So, a lot of different types of

things like that outside of outside

518

of family, we, we are a Disney family.

519

We like to go to Disney world and

Disneyland and enjoy that that side

520

of things as well as traveling.

521

And then, um.

522

You know, I, I, uh, have always been

around, um, technology, but always

523

have had, um, kind of interactions

with video games and end up

524

doing a fair bit of, uh, gaming.

525

When I get a chance, so, um,

classic consoles and and older

526

arcade games is my preference, but

still have the next generation.

527

Consoles as well.

528

Eric Brooke: Cool.

529

Is there a favorite ride at Disney that

you like, or a favorite place to go?

530

Joel Schlundt: Um, I

love the Haunted Mansion.

531

That is probably my favorite go to.

532

And then, um, you know, we just have

family traditions around certain things.

533

Uh, and, um, you know, we always make sure

we have at least one Mickey ice cream bar.

534

While we're at the parks.

535

Awesome.

536

Eric Brooke: Joel, thank you very much

for your time today and your transparency.

537

Really appreciate your time.

538

Thank you.

539

Thanks Eric.

540

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