Welcome to Transform’s People-First Leader Spotlight Series, an exciting journey into the minds of innovative people leaders who are disrupting the now and next of work.
In each Q&A-style article, we’ll introduce you to people-first leaders like Jessica D. Winder, Chief People Officer at Winder Law Firm, who are redefining the boundaries of their industries with forward-thinking ideas and transformative approaches.
“My first job was at Sonic, roller-skating orders to cars in 100-degree Texas heat.
It taught me early that the hardest workers often have the least power—and that’s exactly what I wanted to change.”
About Jessica
Jessica D. Winder isn’t your typical HR executive; she’s the kind who flips outdated playbooks and builds cultures people actually want to work in. A fearless changemaker and truth-teller, Jessica has redefined what modern HR looks like across industries—turning bold ideas into measurable impact. She’s built entire culture playbooks from scratch, implemented livable wage policies before it was trendy, and launched DEI programs that didn’t just check boxes—they changed numbers. Her mission is simple: dismantle performative HR and replace it with people operations that drive retention, trust, and real equity. Jessica doesn’t follow best practices. She creates them.
Leadership and Influence:
Transform: Please share the journey that led you to focus on people-first leadership.
Jessica: I watched too many companies preach “people first” while practicing “profits first.” I set out to build cultures where the message actually matches the behavior.
Transform: Why did you choose to work in this industry?
Jessica: I chose HR because it’s the most direct way to fix broken systems and make work work for people again.
Transform: What was your first job, and how did it shape your perspective on work?
Jessica: My first job was at Sonic, roller-skating orders to cars in 100-degree Texas heat. It taught me early that the hardest workers often have the least power—and that’s exactly what I wanted to change.
Transform: How have your leadership methods evolved over the years?
Jessica: I’ve learned that clarity beats control and respect outlasts approval. Leadership isn’t about being liked, it’s about being trusted.
Vision and Impact:
Transform: What motivates you to prioritize people over processes?
Jessica: Because processes don’t quit — people do. When you take care of humans first, the results always follow.
Transform: Can you share a significant initiative you’ve led that focuses on enhancing employee well-being or engagement?
Jessica: I launched a livable wage policy and rebuilt our Culture Playbook from the ground up. Pay transparency, real flexibility, and inclusive benefits turned engagement from a metric into a movement.
“Leaders who can’t blend tech with empathy will be left behind. The future belongs to emotionally intelligent leaders who can humanize AI, not just implement it.”
Strategies for Change:
Transform: How do you foster a culture of openness and innovation within your team or organization?
Jessica: I create safety first, then challenge everything. When people know their voice won’t cost them their job, innovation stops being risky and starts being real.
Transform: What leadership lessons have you learned that are unique to managing people?
Jessica: You can’t motivate people you don’t understand. Titles don’t build trust; consistency does. And listening will teach you more than any leadership book ever will.
Engagement and Influence:
Transform: How do you engage and inspire your team to adopt people-first practices?
Jessica: I don’t preach people-first, I model it. When leaders set boundaries, lead with transparency, and give credit loudly, the team follows naturally.
Transform: Can you describe a moment when you realized the true impact of your people-first approach?
Jessica: When an employee told me our policies made it possible for her to be a mom and keep her career. That’s when I knew, HR can literally change lives.
Looking Forward:
Transform: What future trends do you believe will further shape leadership and workplace dynamics?
Jessica: Leaders who can’t blend tech with empathy will be left behind. The future belongs to emotionally intelligent leaders who can humanize AI, not just implement it.
Transform: What’s next on your agenda for fostering a more people-centered workplace?
Jessica: I’m focused on rewriting the playbook, normalizing pay transparency, redefining parental leave, and building cultures that don’t burn people out to prove productivity.
“Clarity beats control and respect outlasts approval.
Leadership isn’t about being liked, it’s about being trusted.”
Personal Reflections:
Transform: What is a specific project, initiative, or career highlight you are most proud of?
Jessica: I led the creation of a Culture Playbook that reshaped how leaders show up, how teams communicate, and how employees get recognized. It turned “values” into actions.
Transform: How have you changed as a leader over the years?
Jessica: I’ve traded perfection for presence. Now I lead with clarity, boundaries, and conviction, not busyness or approval.
Transform: Who do you go to for advice and inspiration?
Jessica: Women who tell the truth. The ones building families, careers, and movements, all at once, with no filter and no apology.
Transform: How do you stay current on leadership and management trends?
Jessica: I listen more than I read. Real trends show up in employee DMs and exit interviews long before they hit LinkedIn posts.
Transform: How do you balance the demands of leading with personal wellbeing?
Jessica: I stopped glamorizing burnout. Rest is part of my strategy now, not my reward.
Transform: What is one piece of advice you would offer to future leaders aiming to prioritize people in their leadership style?
Jessica: Stop managing employees like liabilities. Treat them like the investment they are and watch your ROI multiply.
Transform: How do you create work-life balance in your own life?
Jessica: I don’t chase balance, I design rhythm. Some days it’s kids first, some days it’s career first, but I’m always clear on what matters most that day.
Transform: What career advice would you give to your younger self?
Jessica: You don’t have to shrink to fit the room. Build the table, take up space, and make “no” your redirection, not your rejection.
See Jessica speak on the Transform stage at Transform 2026! Secure your ticket now. And check out other insightful Transform Spotlights and thought leadership articles on the Transform Blog.