What I Want in My Next Role (And How I Figured It Out)

As I was transitioning from being a startup founder back into the job market, I felt this weird mix of being overwhelmed with options yet somehow underwhelmed at the same time. Coming from founding a startup after working at both early-stage companies and big tech, I knew this was the perfect moment to really figure out what direction I wanted my career to take next.

Should I stick with the very early-stage startup world I knew so well? Or was it time to try something more established? The current hiring environment wasn't exactly encouraging, but I decided to put on my founder hat and focus on what I could control: figuring out exactly what I wanted and how I'd go after it.

Finding Clarity

I was having one of those meandering career conversations with my mentor when they dropped two pieces of advice that completely reframed how I was thinking about my search. These weren't groundbreaking revelations, but they helped me articulate what had been bouncing around in my head.

"You want the place with the steepest learning curve" and "Find your people."

Simple? Yes. But hearing someone else say it out loud made everything click into place.

What Actually Matters to Me

Once I had that clarity, I realized there were three non-negotiables for whatever came next:

• Staying in the AI Space

  I wanted to continue working in AI, and not just because it's the hot thing right now. I genuinely believe this technology is going to fundamentally change how we live and work. I wanted to be somewhere I could thoughtfully push the boundaries of what's possible with AI and build products that actually matter to people.

• The Steepest Learning Curve

  This one came straight from my mentor's mouth, but it resonated because it captured what I loved most about being a startup founder. As a solo technical founder, I was constantly getting thrown into domains way outside my comfort zone - go-to-market strategy, UX design, branding, fundraising. You name it, I probably had to figure it out on a Tuesday afternoon.

  That experience was incredibly valuable. I knew I brought this unique blend of technical expertise, product intuition, team leadership, and entrepreneurial thinking to the table. I wanted a place that would not only value that mix but give me room to keep growing and pushing myself into new territories.

• Finding My People

  This was the second piece of mentor wisdom, and honestly, it might be the most important one. I was going to be spending a significant chunk of my time with these people, I owed it to myself to make sure I actually wanted to work with them.

  I've learned that I do my best work alongside people who are incredible at what they do but have low egos about it. I was looking for folks who seemed grounded yet genuinely excited about the customers they serve and the mission they're pursuing. People who are comfortable admitting they don't have all the answers but have the drive to tackle bold problems anyway.

  Most importantly, I wanted to work with people who believe we'll go further together - where everyone's unique perspective actually gets heard and valued.

Once I had this clarity, I was able to focus on what actually mattered to me. Instead of getting lost in job titles or company valuations, I had a filter I could apply to any opportunity. Three simple questions:

• Does this place have the steepest learning curve?

• Will I be surrounded by my people?

• Can I continue pushing the boundaries of what's possible with AI?