The Frontier of Chaos: Why The Most Uncomfortable Role Is Usually The Right One

Margaret Leibovic had offers from GitHub and several established companies. Every one of them was in a management role. She turned them all down for the smallest company on the table, in an individual contributor seat.

In this episode of Leadership Recalibrated™, Lori sits down with Margaret, who studied computer science at MIT, built Firefox at Mozilla, and then spent nearly a decade at League, arriving as an engineer and leaving as Senior Vice President. She built the engineering organization from almost nothing, scaled it through multiple pivots of the business, and took two maternity leaves along the way. What connects every move in her career is a pattern she names herself: when things got stable, she went looking for whatever was breaking. The uncomfortable team, the rewrite nobody wanted, the company with no product yet. That is where she found growth — and it is the opposite of what most career advice tells you to do.