Navigating the Career Jungle Gym: Tips from Sidecar Health CTO Rod Barlow
“The Blind Ambition with Jack Kelly” provides a candid look into the top tech companies. Go behind the scenes with tech and workplace leaders and explore engineering and work culture, what it takes to land a role at these companies, and how to build, scale and succeed as an engineer or technologist.
Rod Barlow is the chief technology officer at Sidecar Health. Sidecar Health offers a new kind of health insurance, which aims to be more personalized, affordable and transparent by giving people the ability to pay directly for care. The startup has raised more than $175 million from investors, including BOND, Drive Capital, Menlo Ventures and Tiger Global, at a $1 billion valuation.
Below are some highlights of the podcast featuring Rod. Listen to “The Blind Ambition with Jack Kelly” above or on your favorite podcast app.
How to become a chief technology officer
… I was in a highly technical [role] writing a lot of code into architecture, and then started learning how to lead in a technical and consumer-driven organization.
I actually took a little bit of a gamble [joining Ticketmaster from Shopzilla] because I went to a role where it was a much smaller team. I took on a team of about 10 people, but this team of 10 was inside a massive technology organization… with a steeped history, a 40-year-old technology company.
… I took a bet that I could come in and help transform and shape the culture. And this was a really big breakout opportunity for me.
What I learned… was that in a bigger company, there are so many bright and capable people that might be hiding under a bushel; part of the culture has squished or squash[ed] them into this corner. But really, these are talented, incredible people with tons of potential, and they’re just looking for folks to recognize that, promote them, pull them out of the shadows and help them do great work.
… I took a bit of a 50% bet on myself and a 50% bet on [my manager], and I did well. Soon enough, he was faced with new challenges and needed some big help. So shortly, I was running a team of more than 150 people with some big challenges… for all of the customer touch points for Ticketmaster.com.
How to get recognized at work
… It boils down to the business. Everything we do as an engineer, or a quality assurance engineer, or a data scientist, or data engineer, or native app engineer, it can all be mapped—every single bit of it, whether you’re working on CI/CD, or some concurrent algorithm, or some messaging queue, or whatever—it can all be mapped back to customer value.
So, figuring out how you can shape the product, and the customer or the member experience as an engineer, partnering closely with your product owner, having them recognize you… these are all really, really great opportunities as an engineer to shine and to show what you’re capable of from a customer, member [or] business perspective.
It isn’t always better to work at a large tech company
I know a few folks working at some of the larger engineering organizations, and the challenges they are faced with are just… at a different scale. And as a result, they’re stacked full of engineers, and the challenge there is different. So you might be working on something that’s very, very deep in the technical bowels of a problem and translating that into customer or business value could be more difficult.
But I think the same philosophy is still there: You need to be able to share your worth as an engineer [and] how what you’re doing contributes to the broader company mission, whether in some small way or in some bigger, more noticeable way.
Making the decision between staying on the individual contributor vs. management career track
… You can grow in your career along that engineering individual contributor track, and this is certainly true of all of the companies I’ve worked at since I’ve been here in Los Angeles.
… This means, as an individual contributor, you can continue growing your impact; you can continue growing your comp[ensation] along that individual contributor track… There’s no need to jump over to management to continue advancing your career and advancing your situation for yourself and your family.
And so this is really, really great. Because by the way, management may not be for everyone; it is a really tough job. The expectations of a manager are completely different than the expectations of someone on the individual contributor track.
One piece of advice that I would love to give here is to find a way to test it out. Internal mobility is a really, really great thing at an organization. If you like the organization you’re with, I would encourage you to find a way to test out a different track, jump on that jungle gym… and find a way internally to test out [and] jump into a leadership role some way, somehow.
What is it like being an engineering manager or leader?
It’s hard to make that pivot… It’s kind of no longer about you, and a lot of people have difficulty making that transition. It’s [leadership] about you empowering, unlocking, coaching, challenging, guiding [and] mentoring your people.
What some folks also don’t recognize is that now you have two teams. You’re not just getting one team; you have two teams. Imagine a capital “T:”
- You have your people down the “T.” Down the line vertically, they’re your people; you are entrusted with these people… that’s your direct team.
- Imagine the horizontal on the top of the “T.” They are the folks like the product owner, the business stakeholder, the designer, the project manager, whoever that might be across that horizontal on the team—that’s your second team. They have a whole bunch of expectations for you now as a manager.
Important skills every engineering leader should have
… A really, really important thing if you’re interested in management is having a growth mindset, particularly where you see talent…
Another skill that I believe is important is being decisive. If you have a poor performer, help and support them, but also get yourself to the point where you can make a tough decision if it comes to that.
… As a manager and a leader, it is super important to be able to recognize and challenge the status quo so that [y]our teams and [y]our people can continue getting better.. If leaders aren’t in [a] place… to recognize and challenge that status quo, the cruft will just continue accumulating.
Quit your job when you are “pickled”
Sometimes you see people… that [say], it can’t be done or the problem with that is… and the way to frame it is they’ve been sitting in the brine too long. They’re pickled…
And those people, in order to reset, they need to go elsewhere; they need to go to a different company to kind of shake it off and do something different and to be able to start afresh and reinvent themselves.
Every time you start a new role or [at] a new company is a really good opportunity to reinvent yourself.
The need for career confidants
My number one thing is finding your career confidant. Who are your three to four career confidants?
I would encourage folks that are feeling pickled to reach out to their career confidants and leverage these folks in your decision-making process [to] help you find a path to something you’re going to love…
If I call these people up, they’re there… I can count on them to hear me out and give me advice… I would encourage you, if you’re pickled, or you’re thinking about making a move, to find these career confidants and beat up the idea that you’re thinking about.
How much coding engineering leadership actually does day-to-day
I think back to when I moved over to a management role; I found myself on the weekends doing coding challenges by myself because I felt uncomfortable moving away from the code.
As an engineering manager at Sidecar Health, you’re probably writing a little bit of code around the edges, maybe around 25%. Your responsibility is really the people that entrusted to you their growth and development, ensuring they’re challenged and satisfied and looking after themselves and able to contribute effectively.
As a tech lead, you’re coding probably 25% to 50% of your time and then mentoring through working on the code or mentoring through designing a part of the system. Tech leads do[n’t] have direct reports. It’s a way of testing out… the management track.