In 2018 I joined Octopus Deploy as an Sales Engineer. By 2019, I was a Vice President of the Customer Success team on the executive leadership team, helping guide a fast-growing company from 70 people toward 150 and beyond.

From the outside, it looked like success. Inside, it felt misaligned. I was never a natural strategist, disliked budgets, dreaded performance reviews, and quietly kept one foot in hands-on work. In 2022, when an opportunity arose, I volunteered to step down to an IC role—an unconventional move that proved transformational.

This talk explores why management isn’t the only path forward, how scaling organizations can outgrow leaders (and vice versa), and why honest self-assessment matters more than title.