Lee Matos

This week – and I’m thrilled to have tracked him down – let’s absorb some of the learnings of Lee Matos!

Lee is a Support Engineering Manager at GitLab, a complete DevOps platform, delivered as a single application. GitLab covers all things from project planning and source code management to CI/CD, monitoring, and security.

Lee has been in leadership for six years, the last three of which have been at GitLab.

Hey Lee!  Thankyou for spending some time with me today. I’d love to know first what your early career looked like.

My first ever role was as a Sales Associate at a College Bookstore. My first real official job was in Technical Support at Linode. I always loved computers, had some skills, and they hired me.

Why did you choose Tech Support?

I hold a strong hypothesis: As computers become more prevalent, and more people learn how to program, the people that will be valuable will be the people that can troubleshoot technical problems effectively.

How did you make the move into leadership?

First, at Linode. It was an arduous process because I was young and cocky, but I was promoted internally. I left there to join an early stage startup and build a team… and then left that startup to join GitLab as a individual contributor. Eventually, I made my way back to leadership.

The transition to leadership is hard in that your work is not as immediate as tickets. You need to learn how to be kind, direct, and process-oriented all at once.

Would you say the early stage of leadership is the hardest? What challenges have you faced?

At Linode, it was just having a voice. I was a new manager, and felt I had no say. I felt I needed to prove myself.

At One Month, hiring was my biggest challenge. Just building a job description, hiring plan, and executing.

At GitLab, the challenges are bigger. Here, I’m hiring managers, and also managing up to a large group of executives.

Do you think CS leadership is different to any other leadership role?

Yes. Compared to engineering leadership our role is reactive. Any tasks we want to do can slip indefinitely due to the continuous incoming ticket volumes.

We are also often disenfranchised from solving our own problems. It can feel like we are the “face” but have no power.

The ever-competing priorities with engineering and product teams mean a part of it is just jockeying for position to get problems solved.

What skills make a good CS leader?

Patience, being process-oriented, being data-aware. And the ability to build trust.

How do you measure your team’s success?

I have my own personal goals, but in addition there are traditional KPIs such as CSAT and FRT. I also have hiring and retention targets.

What’s your general approach to metrics?

They are a tool, but they become increasingly ineffective as a “target”.

What’s been the hardest thing you’ve had to do or learn?

Managing up.

What’s the biggest gap between what you thought leadership would be like, and what it’s actually like?

I spend a lot of time thinking vs. doing, because my impact is a lever. Any decisions I make have a large blast radius.

Looking back, what do you know now, that you wish you knew then?

Time Management is ESSENTIAL.

And, since endings are always important, my favourite question for last – what’s your favourite way of signing off an email? 

“With a wikipedia random link. Go ahead, try it: https://en.wikipedia.org/wiki/Special:Random“

Ohh, interesting! Thanks, Lee.

Transitioning to leadership is hard. And, as Lee says, it’s not just hard the first time. Moving into any leadership role will have challenges, and they’ll be fairly unique to that organisation.

I’m probably off on some Wiki goose chase now…

More CS Leader interviews coming soon!