In this episode of Clover, I sit down with my former teammate Jordan Lea, now VP of Customer Experience at Plum, to talk about bold career leaps, people-first leadership, and building a meaningful career on your own terms. Jordan shares her journey from a tiny town in North Carolina with dirt roads and cornfields to moving to New York City with no job lined up, flying standby for interviews, taking an unpaid internship in fashion, becoming employee #5 at a fashion tech startup, and eventually finding her sweet spot in HR tech and customer experience.

We dig into what it really looks like to grow up inside startups; wearing every hat, building resilience, and learning to say “give me whatever you’ve got” instead of “that’s not my job.” Jordan talks about how she evaluates new opportunities by looking beyond the job description and title to the company’s mission, timing in her personal life, and whether there’s true alignment with what she cares about. We also get into culture (beyond the buzzword), psychological safety, and her “skill vs. will” framework for coaching and developing people. She shares practical advice for women who feel boxed in or underestimated at work, how to make intentional career pivots into new industries, and how AI can actually free CX teams to be more human, not less.

You’ll hear us talk about:

• Taking big leaps: moving to a new city with no safety net, changing industries, and asking “What’s the worst that could happen?”
• Startups as a career accelerator: why being early-stage employee #5 shaped her leadership, adaptability, and ability to “Sherpa” others through growth.
• Skill vs. will: how she decides when to invest in someone’s potential versus when there’s a true mismatch.
• Building real culture: trust, authenticity, and psychological safety as non-negotiables, not just slide-deck values.
• Career pivots with intention: how to research new fields, show up prepared to conversations, and decide if an opportunity is a “go” or “no-go” for your life.
• AI + Customer Experience: using AI to streamline the boring parts so humans can focus on relationships, storytelling, and proactive support.
• Her surprisingly fun productivity hack (involving a giant medicine ball)

If you’re a woman in leadership, or aspiring to be one, who feels ready for your next leap but isn’t sure what it looks like yet, this conversation with Jordan will give you both the mindset and the practical tools to start moving.

Connect with Jordan on LinkedIn!