This is Leadership On New Terms, a series with the senior leaders renegotiating the terms of work as AI rewrites the work itself.
When I asked Jordan Taylor what term of her old corporate roles she would never accept again, she named a way of thinking. The thing she would not go back to was a predefined recipe for solving problems.
“I’m a very creative problem solver,” Taylor told me. “I don’t just see A to B to C. I see, you know, maybe we go to A and then D and then to C.” For her, the deal-breaker is any role that takes that route away or locks the path between problem and solution before she has had a chance to look at it.
Taylor is the co-founder and CEO of Medley, a group coaching platform that builds leadership development programs for enterprises. She started her career at BCG, spent time at the digital media company Mic, and graduated from Harvard Business School into a class where most of her peers headed back to consulting or to large organizations. She went a different way. She started a company with her mother, Edith Cooper, the former head of human capital management at Goldman Sachs. Seven years later, Medley works with enterprise clients on cohort-based coaching programs that scale across thousands of employees.
Her path is part of a much bigger pattern. According to Gusto’s 2025 New Business Formation Report, women started 49% of all new businesses in 2024, up from 29% in 2019. The single biggest reason women in Guidant Financial’s 2025 Women in Business survey gave for becoming business owners was the desire to be their own boss, with dissatisfaction with corporate America close behind.
Here are some of the most useful lessons from our conversation:
When Taylor talks about what made her leave the consulting track, she focused on the gap between solving a problem and owning what happens after. At BCG, she liked the work and the people. The piece that did not fit was structural: Consultants advise on the outcome. as opposed to living with it.
“Being able to create something, move quickly, see what happens, and own the consequences were things that were attractive to me... I definitely did not recognize or appreciate just how much of a journey entrepreneurship really would be. But I think it was that blind desire to experience really creating something new and owning an end-to-end that had me take the leap.”
Corporate ladders compensate well for execution, but they reserve ownership of outcomes for a small group at the top. Most senior leaders never get within reach of it. The wave of women going independent right now is partly a response to that math.
Medley caps its client base at seven to ten enterprise customers a year. Taylor says she would consider it a failure if the company grew faster than that. The math comes from what happened in early 2023, when Silicon Valley Bank collapsed in the middle of Medley’s Series A process. Term sheets evaporated overnight. The team had to figure out how to operate without the venture round they had been counting on, and the constraint reshaped the business.
“We don’t want to spend millions of dollars on marketing in a year when we know that there’s an alternative path of us growing a little more slowly, being a lot more sustainable, and [being at] the brink of profitability. I have to say that’s been a real silver lining of that whole process because that was certainly a challenging couple months.”
The deeper move is what Taylor did with the constraint after the immediate crisis passed. Taylor used the moment to redraw what success looks like for the company: fewer clients, deeper integration, and expansion within accounts rather than logo accumulation. That is a renegotiation of pace as much as scope, and it gave her control over a variable most VC-backed founders give up.
Coaching is one of the categories AI is most aggressively reshaping. Plenty of platforms now offer coaching bots tailored to enterprises and individuals. Taylor watched the shift and decided Medley would not build one. Her bet is that the premium enterprise clients pay sits in connection, empathy, and relationship-building between humans, while AI absorbs the question-asking, role play, and mirror-acting layers of coaching underneath.
“The outcomes that we see, which are really around greater connectivity, greater relationship building, more self-awareness and interpersonal skills in themselves are going to be harder to replicate from an AI coach bot standpoint. So we’re leaning into what we’re great at while also making sure that we are as smart as possible on how AI is enabling our workflows and our operational processes.”
Every leader is now running some version of this exercise on themselves. What is unique to the human in the role, and what is automatable infrastructure around them. Taylor’s answer, when I asked her to apply the same question to her own work, was specificity of judgment. She named her ability to move between altitudes, her relational care for a 10-person team, and the pattern recognition that comes from having sat in many rooms across many different kinds of organizations. Her co-founder, Edith Cooper, made a parallel argument in a recent article on LinkedIn, reading AI as a moment that demands judgment, discretion, and intentionality from workers rather than a tool that absolves them of needing those skills.
The leverage point Taylor renegotiated when she launched Medley is scope — specifically, scope of method. In a corporate role, scope is usually framed as how much of the org chart sits under you. In Taylor’s framing, scope is the range of legitimate paths between a problem and an outcome. The old terms gave her ownership over deliverables and almost no ownership over how she got there. The new terms reverse that.
“I want to make sure that I’m able to exercise that creativity, have that ownership that’s so important to me, and retain autonomy in how I get to the shared goals, even if they’re defined by someone else. The amount of ownership that I have over the outcome has really been very motivating to me.
Know a leader who is charting a career path on their own terms? Reach out so I can consider interviewing them for this series. And if you want this in your inbox for free, subscribe here.
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