From Dev to VP: The Roundabout Way

I’m sharing this for anyone stuck between roles—feeling like they’ve outgrown one but haven’t yet earned the next. For the developer who thinks differently and wants something beyond where they are currently. For anyone who’s felt like they might be in the wrong seat, but not sure how to change it. This is how it happened for me. And what I learned along the way.

The Early Years

I spent about 7 years as a developer. Then 2 more as a technical lead.

It took me 7 years to get my first promotion. Not because I didn’t care, but because I was waiting for people to value me instead of asking how I could be more valuable to them.

That shift—changing my posture from “why don’t they see me?” to “how can I help?”—was the beginning of everything.

Early Signs

At one point, I thought I wanted to get into project management. I was excited about capturing and improving our release process so it could be reused and scaled. That was meaningful work.

But somewhere along the way, I realized it wasn’t quite for me. (A story for another day—but I still have huge respect for my project management colleagues.)

Then we started exploring Agile as a team, and that’s when it clicked. I realized what I loved was synthesizing problems. Telling the user story. Making sense of ambiguity so others could act on it.

Around that time, I did a Colour Insights profile—Red-Yellow. Motivating. Visionary. People-focused. Not exactly your classic detail-driven Cool Blue developer profile.

That explained a lot. 🤦

I still had a lot to learn, but I started wondering if I was in the wrong seat. Or at least that I could be doing more good from another one. I didn’t want to just work inside the system. I wanted to help shape it.

The Blunder

I reached out to our lead product manager and asked if I could join her team. We set up a simple coffee chat, but really, I should have treated it more like an interview. I should’ve known better.

I made a blunder. I actually said I didn’t want to “do grunt work”—I was trying to convey I liked automating and improving processes. But it came off wrong. It sounded like I didn’t want to roll up my sleeves and be a team player. I didn’t get the job.

I felt stupid. Like I’d put my foot in my mouth. And I carried that chip for a while.

Turning Point

But I didn’t let it fester too long. I started working on myself.

I made some big personal changes around that time—started reworking my habits and mindset. It wasn’t all at once, but the shift stuck.

Instead of fixating on what I couldn’t do, I focused on how I could help. I offered to liaise. I stayed close to product. I made myself useful. I showed up. People noticed.

Eventually, the lead PM was promoted. The next logical person to succeed her got another specialized role. There was a vacuum—and my boss put my name forward (I'm so grateful for that).

That’s how I stepped into product. And not just as a PM—into a VP role.

Stepping In

It was a lot to take in. I had to learn the job while leading a brand-new team: a mix of tenured folks, new hires, and people with more experience than I had.

What surprised me most was their willingness to take direction. I stepped in with respect, and they showed up with trust.

I had impostor syndrome, no doubt. But I also had drive, enthusiasm, and deep product knowledge from the inside out. I started digesting as much information on product management as I could find.

One of the first things we did was align around an Agile backlog. We groomed user stories together. It gave us shared clarity—and built trust fast.

Honestly, I felt ready. I’d been leading community groups and charities for years. If you’re looking to build leadership skills, volunteer roles can be a great place to practice what might not be available to you in your day job right now.

Letting Go

One thing I don’t often talk about is that part of stepping into this role meant stepping away from something else.

It wasn’t the only reason, but it was a big one. I’d been president of the Kodály Ensemble for 10 years. That role was part of who I was.

Letting it go hit me harder than I expected—stepping away after 10 years left a real emptiness. I wasn’t prepared for how much that role had become part of me.

But then my daughter was born. And I started this new chapter. The pain of that sacrifice started to feel worth it.

Closing the Loop

What helped me most was developing an action bias. Do something. Volunteer. Learn. Build. You can only think your way through so much—most of the growth comes from doing, failing fast, and often until you succeed.

Even small things helped—changing my diet, moving more, feeling better in my body. That positive feedback loop—physical momentum feeding mental clarity—became part of how I grew into this next chapter.

I’m also deeply grateful to the leaders, mentors, and colleagues who trusted me, challenged me, and gave me space to grow, especially when the path wasn’t straightforward. The opportunities I’ve had and the support I’ve received made all the difference.

It’s only in hindsight that I can see how all the pieces lined up toward this role.

A Few Things I Learned Along the Way

1. You don’t get promoted for waiting to be seen. You grow by showing up, putting in the work, going above and beyond and speaking up. For a long time, I thought promotions came from being noticed. In reality, things started to shift when I stopped asking why not me? and started asking how can I help? That mindset helped, but so did getting clear about what I actually wanted. I had to be vocal about my goals. I had to let people know I was ready to grow. Doing the work matters. So does making sure the right people know why you’re doing it.

2. You can start building toward the next role long before you’re officially in it. Before I had any product title, I was already liaising, capturing processes, improving workflows, and synthesizing problems. I didn’t call it product work. But in hindsight, that’s exactly what it was. Sometimes, you grow into a role by doing the work that leads there—quietly, steadily, and over time.

3. The mistakes you make can teach you more than the wins—if you let them. When I didn’t get the role the first time, it stung. I’d misread the situation, said the wrong thing, and left a poor impression. But that moment kicked off a string of changes: I reflected, shifted my mindset, and started making more deliberate choices about how I showed up. That rejection gave me a roadmap—if I was willing to read it.

4. You can only grow so far without working on yourself outside of work. The professional shift came alongside personal ones. I changed my habits, started paying more attention to my health, and let go of things that were draining me. That momentum carried into how I led, how I thought, and how I showed up for others. The growth wasn’t just strategic—it was personal.

5. Skills built in community and volunteer roles are real—and they translate. Years of leading in community spaces gave me experience I didn’t even know I was building. When the VP role came, those muscles—alignment, facilitation, mentorship—were already there. If you’re not getting leadership opportunities at work, you can still develop them elsewhere. It counts.

I'm sure I’m not the only one who’s taken the roundabout way into something new. If you’re in that in-between space—outgrowing where you are but unsure what’s next—what’s helped you keep moving? Or if you’ve already made a shift, what did you learn that others might need to hear?

If you’re working through your own roundabout path, I’m happy to offer what I’ve learned—no playbook, just patterns that helped.