Medley Moments: A Conversation with Jordan Taylor

For the first installment of our Medley Moments series, Edith Cooper is sitting down with her Co-Founder (and daughter), Jordan Taylor.

For Edith and Jordan, building a company has been a huge learning curve. The journey hasn't been linear; it's certainly had its ups and downs. But Jordan and Edith are energized for the opportunity ahead of them. Join them for a discussion where they'll reflect on the journey to date and share more about their vision for the future. They'll also share their perspective on navigating this challenging environment and what they are hearing and learning from extraordinary leaders.

Q: Jordan, What led you to start Medley, and what has surprised you about the ups and downs of being an entrepreneur?

A: Oh my gosh, the ups, the downs, the why — lots of big questions! Before I even knew what Medley would be, there was a period after I graduated from business school where I had an instinct about how groups can help people grow. I’ve always had my greatest growth experiences in team and group environments. As an adult, it’s hard to find that same sense of connection. At the same time, everyone is navigating life, figuring out what they want at work, how they want to lead, and how to influence others — but there wasn’t a great place to do that.

After I graduated, I remember when you [Edith] suggested that we build Medley together.

Our "why" has been clear from the start — helping people grow through connecting with others in groups. It’s shifted and grown as we’ve realized that companies need Medley now more than ever before. That’s been exciting — our "why" has continued to evolve as we’ve learned more about our customers on both the individual and organizational sides.

Q: Over the past four months, as we’ve had more conversations with companies — 50 to 60 CHROs across different scales and types — it’s clear that talent is looking for something different. How have things shifted over the past decade in terms of what companies need, and what have you heard from business leaders?


A: Over the past 10 years, the world has changed dramatically. In 2013, it was pre-pandemic, social media was slower, and Gen Z wasn’t yet entering the workforce. Today, we have much more social unrest, faster social media, and an economy that’s more uncertain than it was during the boom period. If the world is changing rapidly, it makes sense that people’s experience at work is also changing. People’s expectations from their companies and managers have evolved, making the role of a manager more complex than ever.

I remember a conversation in October with CHROs where you, Edith, mentioned that the challenges today are much greater than during the financial crisis of 2007-2008. Back then, you were dealing with economic uncertainty, but today’s leaders are juggling economic uncertainty, social justice issues, and even playing the role of a chief medical officer. We can’t keep doing the same things from a talent perspective and expect different results. People’s needs are different now, and as a result, we’re building a greater vocabulary around growth, leadership, and impact.

Q: How do you think about your leadership style, and how has it evolved since we’ve started working together at Medley?

A: I think the big thing I’ve noticed is that the definition of leadership has expanded.

There’s not just one way to be a great leader, and what works for one person might not work for another. For me, continuous learning and growth are key. I also believe that listening and empathy are central to good leadership. Self-awareness is important too, which doesn’t mean always having full control, but being curious and open to feedback.

In terms of my own leadership style, I think I’m great at connecting with people. I genuinely enjoy getting to know others, and I believe that curiosity leads to stronger connections, regardless of style.

Q: As an entrepreneur, how do you deal with the ups and downs, especially given the constant uncertainty?

A: The hardest part is staying connected to the things that keep you grounded throughout the highs and lows.

Building a business means getting comfortable with hearing a lot of "no"s before you get to the "yes"es.

It’s something I’m still working on, but I’ve gotten better at staying connected to what grounds me — whether it’s spending time with family, friends, or my dog Howie. I remind myself that even during difficult periods, they aren’t permanent, and time always moves forward.

Q: We’ve had to recalibrate our growth plans and make difficult people decisions. How have you shown up as a leader during this time, and what advice would you give to others facing similar challenges?

A: For me, it’s about transparency and openness. I try to be clear with the team about where we are, what we need to do, and what risks we face. Everyone on the Medley team is bought in and cares deeply about what we’re building, so we’re all rowing in the same direction.

It’s also been inspiring to see some companies recognize that, even in uncertain times, investing in their people is critical. Employees appreciate that investment, and it helps keep them motivated.

Q: What role does Medley play in your life, and how does it contribute to your personal and professional growth?

A: Medley, for me, is about perspective and commitment. I thrive in teams and groups, and I’ve always sought out those connections in my personal life. Whether through friendships or formal groups like a women’s circle or a founder’s group, those relationships ground me and help me keep perspective.

Q: What feedback are you getting from people in Medley coaching groups? Are we delivering what our members need?

A: People usually come to Medley for growth, but they often leave with an appreciation for the meaningful relationships they’ve formed. The vulnerability and connection in the groups are powerful, and we often hear that members feel more grounded and have gained new perspectives.