While rising up through the ranks, there are definitely some do’s and don’ts when it comes to focusing your efforts. The CPO is a unique position that merges different departments and skills. What are some areas to hone in on to efficiently progress your career as a CPO? GitLab Chief Product Officer Scott Williamson shares his career development journey from sales to CPO, and lessons he learned along the way.

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On 4 lessons from sales to CPO

Scott reflects on some lessons from his career progression from sales, to strategic alliances, to product. The first of these lessons was to prioritize “learning curve over comp and title. If comp was all that was important to me, I would have stayed in sales, because sales pays well, but I was more intellectually interested in product management. Nor would I have done a full time MBA, because there’s a high opportunity cost there. But I felt like getting on that learning curve towards being in product was important to me, and it was worth it worth the cost hit. 

“Two is: be intentional. I knew what I wanted out of the MBA; I think that helped me get in. And it helped me maximize the experiences that I had while I was in grad school. Three, be patient. It took eight years for me to bridge from sales over to product management. That was a long time, frustrating at times. But I kept my eye on what I wanted to do. And then I enjoyed the side roads I was going down. I learned as much as I could out of sales. I learned as much as I could out of the MBA. I learned as much as I could out of strategic alliances. And as it turns out, all those experiences ended up differentiating me in my product leadership role.

“Fourth, seek out mentors. The CRO that [mentored me] was a really pivotal person for me to have worked with. I got lucky because he was my boss. And he saw something in me, and was very generous with his time and advice. He wrote me a reference letter and really helped me see what the next step should be. If you don’t have that person as your boss or someone that you’re working closely with, seek someone out who can help give you advice and help you think through the next steps.”

On how not getting the job can be a positive

While working as a Senior Director of Product at Colorado startup SendGrid, Scott applied for the newly created position of Chief Product Officer. He didn’t get it, but it opened up an unexpected opportunity: the chance at invaluable career development which set him up for better career progress down the line.

“I was not happy. I felt like I deserved the benefit of the doubt. But the CEO had the obligation to hire the person that he thought was was strongest for the role. And so he went another direction. 

“But I quickly came to find out that the person that was hired for the role could teach me a lot. And he came in and very quickly proved to me that he was serious about my career development, really wanted me to thrive and succeed, and really leaned in on all kinds of things to help me advance quickly. And so he won my confidence, and I decided to stay. 

“Over the next two or three years, we did several things. We took a class together called Top Performer, which involved me interviewing 10 VPs of Product. At that time I was a Senior Director. And so I talked to people who were a step ahead of me. He hired a coach for me. The purpose of it was to train me to be a CPO down the line.”

That career progress training paid off when Scott landed his current role, as the CPO of GitLab.

On future authoring

Be intentional about your future. Write down where you want to be and what kind of work you want to be doing in 5 years. Scott says this kind of intentionality has helped him greatly in his career progress. In one role, Scott used an evergreen one-year career development plan where he and his boss agreed on the things he was going to be working on. They tracked progress with check-ins.

Probably the most valuable exercise, Scott says, was something called “a future state doc. It’s about five years out into the future. And it says, what do I want to be doing in five years? Not so much title, but what kind of work do I want to be doing? What does the environment feel like? What gives me joy from this particular job? And even though I’m a fairly introspective person, that exercise was super valuable, and it really crystallized what kind of environment I wanted to be in.”

“At GitLab we use a career development framework that lays out our expectations along four different dimensions: validation skills, build skills, presentation skills, and communication skills. And we have conversations at least once a quarter, usually every two months, with each person to reflect on: Where are you against those expectations? What have you done that represents those expectations? What could you work on to get better at each of those expectations? 

“So if you have a framework like that, I’d encourage you to review that with your manager often, to make sure you understand where they think you are and what you need to work on. If you don’t have it, feel free to borrow GitLab’s and do your own reflection on where you are against the various skills that are relevant.

About the speaker
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