Conversation
Highlights

In this episode of Whispered Hiring, Josh Hanewinkel speaks with Whitney Littman, Vice President of Customer Success at ZoomInfo, about building high-velocity hiring systems for customer success organizations in AI-native GTM environments. Drawing from seven years scaling CX at DocuSign and her current role leading post-sales strategy at ZoomInfo, Whitney shares her framework for maintaining evergreen talent pipelines, her three-part candidate presentation evaluation system, and why unqualified work-life balance questions from senior candidates signal prioritization deficits. Her approach reveals how to maintain hiring velocity without compromising quality standards.

Topics discussed:

• How evergreen requisitions close the sourcing-to-seat gap for high-velocity IC roles by arming TA teams with precise filtering criteria: data expertise level, industry type experience, and market segment fluency. When hundreds of applications flood in, recruiters can disqualify quickly because they know exactly what matters.
• The three-part presentation framework that separates strategic thinkers from performers: running cycles with hiring managers to clarify prompts and validate data interpretation, taking defensible positions on incomplete information, and simplifying complex analysis without toggling between multiple spreadsheets.
• Why case studies are mutual evaluation tools: Whitney’s leader invested 90+ minutes walking her through ZoomInfo’s data model before her final presentation, revealing the company’s commitment and her willingness to seek clarification rather than guess.
• The “two coffees per week” networking discipline for maintaining executive relationship capital with no agenda beyond understanding people on a personal level rather than transactional business reviews.
• Why Whitney’s best hire wasn’t the strongest individual performer but the talent magnet who attracted people she thought they had no business hiring and built multiple CS teams from scratch.
• The controversial read on unqualified work-life balance questions from director-plus candidates: if you can’t qualify why you’re asking, it signals an inability to self-manage competing demands. For senior leaders, it suggests you expect someone else to structure your day.
• Hiring from your customer ecosystem: navigating cease-and-desist risk while leveraging champions who understand your product and creating reciprocal talent intelligence when customers request referrals.
• Assessing AI fluency indirectly by asking about scalability challenges, then observing whether candidates default to legacy automation or proactively discuss AI-enabled approaches.

ABOUT YOUR HOST: 

Josh Hanewinkel is a startup builder and operator who thrives at the intersection of strategy, operations, and talent. As a two-time unicorn executive and advisor/GM at Whispered, Josh has spent his career helping fast-growing startups scale by building high-performing teams, creating customer-centric cultures, and leading through ambiguity. He’s held Chief Customer Officer and VP roles at companies including DataGrail, People.ai, and Mixpanel, where he’s rebuilt and scaled teams across customer success, talent acquisition, and revenue operations. From leading customer success teams to 150%+ NRR to transforming recruiting functions into high-velocity talent engines, Josh has seen firsthand how the right people in the right roles can change the trajectory of a business.

Learn more about about Whispered: www.whispered.com