A Dialogue with Bree Gillespie & Patrice Castellano
When it comes to blending strategy, product ownership, and the human side of tech, few do it with as much creativity and energy as Bree Gillespie, Vice President of Client Engagement. Bree has helped countless organizations turn big-picture visions into real-world results, always keeping things approachable, inclusive, and fun.
For this conversation, Bree sat down with her colleague Patrice Castellano, Director of Support Services, to talk leadership, women in tech, and what it really takes to make strategy stick. Their candid Q&A touches on everything from bold ideas and product ownership to coffee, playlists (PRINCE!), and the future of women in leadership.
Patrice: Let’s start light. What’s one word your team would use to describe your leadership style?
Bree: Ha, maybe not so light! But I’d say “direct.” I’ve learned that honesty and clarity go a long way, especially for women in leadership roles where it’s easy to second guess. I also think “growth mindset” is part of my style, it’s not one word, but it matters in both sports and leadership.
Patrice: You’ve worn many hats including strategist, product owner, and consultant. How do you know when to zoom out to the big picture and when to dive into details?
Bree: It’s really about the process. You have to evaluate where you are and what will have the biggest impact. Sometimes that means big picture visioning, sometimes it means narrowing in on details. I think of it as convergent and divergent thinking, a funnel that expands and contracts depending on the stage of the work.
Patrice: Strategic planning can sound a little stiff. What’s your favorite way to make strategy feel alive and fun?
Bree:
I think of strategy as creative problem solving. At its heart, that’s exciting. When you keep people at the center, making sure it’s interactive, human, and focused on real change, it becomes inspiring instead of overwhelming. Strategy should be about making lives better, not just creating a list of tasks.
Patrice: Product ownership is a balancing act with features, bugs, deadlines, and big ideas. What’s your secret sauce for keeping it all moving without losing the human side?
Bree: Teamwork. None of it happens without a strong team. I see myself as one cog in a bigger wheel, and when it comes to the human side, I always try to see through the lens of real world impact, how the product actually helps organizations and the people doing the hard, important work in their communities.
Patrice: As a woman in tech, what’s been the most surprising or funniest moment you’ve had breaking into the space?
Bree: Honestly, just learning with open eyes. Tech is one of those areas where you never “arrive,” there’s always more to learn. Staying humble and open has been the biggest key to success.
Patrice: If you could rewrite the rules of leadership for the next generation of women, what would you toss out and what would you keep?
Bree: Toss out doubt. Take up space, speak up, and don’t be afraid to push. Everyone deserves a seat at the table, and we can set the example by showing up fully every day.
Patrice: What’s the boldest idea you’ve ever pitched in a strategy session or product meeting? Did it land or flop?
Bree: Oh, plenty of flops! That’s the nature of innovation, you have to be willing to let go of a lot of ideas, even ones you love. Every so often, one sticks. Recently I pitched a product extension idea, how to add more value for clients through tech that makes life easier for end users. That’s the kind of impact that lasts.
Patrice: Everyone talks about innovation, but what does it actually look like in your daily work?
Bree: For me, it’s constant rethinking, what can be better, what’s next, how do we improve? It’s fun to chase the big idea, but a lot of innovation comes from revisiting the plan, iterating, and making sure the small details line up so the big impact can happen.
Patrice: Coffee, playlists, post-its… What’s your non-negotiable tool when you’re deep in planning mode?
Bree: A homemade latte with honey from my Aunt Dot’s bee farm. Nothing else compares.
Patrice: Last one, what advice would you give young women who want to lead in tech or strategy but don’t see many role models who look like them?
Bree: If the elevator tries to bring you down, go crazy and punch a higher floor. (Thanks, Prince!) Don’t stop until you get what you want and deserve.
Interviewing Bree reminded me that leadership isn’t just about strategy or great products, it’s about staying human, curious, and open to possibility. Bree embodies all of that and more. My hope is that readers leave with the reminder that women in leadership are shaping the future of tech and strategy in ways that are both bold and approachable.
Until next time,
Patrice Castellano, Director of Support Services