Reclaiming Self Beyond the Roles: Identity, Boundaries, and Choosing Yourself in Every Season
with Nephtalie Dujour
How to Run Discovery Calls That Actually Convert
Eulynn Gargano, Brooke Caughran
June 17, 2026 01:00 PM EDT
June 17, 2026 01:00 PM EDT
Virtual
Join two of Zillow's top sales leaders to learn how to transform discovery conversations from routine check-ins into real opportunities. The skills that make a great discovery call, asking the right questions, listening with intent, and uncovering what someone actually needs, are the same skills that make anyone more effective in their role.
Whether you're in sales, account management, partnerships, marketing, or customer success, this event is for you. It's also a great fit if you're curious about a career in sales or considering a pivot. Come ready to learn, ask questions, and connect with like-minded professionals invested in growing their skills.
What you'll take away
- What makes a discovery conversation actually work — The mindset shift that separates high-impact conversations from ones that go nowhere, and why the best outcomes start with listening, not talking.
- A repeatable framework for uncovering real needs — A structured approach to asking better questions and understanding what someone actually needs before jumping to solutions.
- How to build trust quickly and keep it — How top professionals establish credibility early and create dialogue that people genuinely want to act on.
- Skills that travel across your career — Hear directly from Zillow's leaders on what it takes to show up as a trusted partner in any role, not just in sales.
You'll walk away with concrete techniques you can apply immediately, plus the chance to connect with a room full of professionals all here for the same reason: to get better at what they do.
Meet The Speakers
Eulynn Gargano
Senior Manager in Strategic G&R Agent Software and Advertising, Zillow
Eulynn Gargano is a Senior Manager in Strategic G&R Agent Software and Advertising at Zillow, where she leads at the intersection of sales strategy, customer insight, and product value. She has a strong track record of building and leading high performing teams, driving meaningful results, and shaping programs that scale across the organization. Widely recognized for her expertise in discovery, Eulynn has helped redefine how teams approach customer conversations by focusing on curiosity, precision, and deeper problem understanding. She equips teams to move beyond surface level questions and uncover the insights that truly drive decisions. Her work centers on shifting mindsets from pitching to diagnosing, enabling more human, effective interactions that build trust and deliver stronger outcomes.
Brooke Caughran
Senior Sales Manager for Enterprise Rentals, Zillow
A former Division I volleyball player turned sales leader, Brooke Caughran’s career has been defined by adaptability, leadership, and a passion for developing others. Brooke began her professional journey as a 5th-grade teacher and high school volleyball coach, where she discovered her love for mentoring and inspiring growth in others.
A life transition came when she met her husband, a U.S. Marine stationed at Camp Lejeune. During that time, Brooke embraced change and entered the world of sales. As the couple transitioned out of the military and relocated across the country, Brooke pivoted again—this time stepping into tech sales in Denver, Colorado.
Through connections, Brooke was introduced to Zillow, where she saw endless opportunities for impact and advancement. Over the years at Zillow, she has progressed from Account Executive to Regional Sales Manager, a promotion earned through Zillow’s Leadership Development Program, now is the Senior Sales Manager for Enterprise Rentals.
Brooke leads high-performing sales teams and takes pride in developing future leaders across the organization. She has guided team members into enterprise and leadership positions, led impactful projects and events, and contributed to fostering Zillow’s culture of growth, collaboration, and innovation.
