Three veteran CHROs join Pinnacle as strategic advisors

The AI coaching market is flooded with one-size-fits-all solutions that miss the mark. Meanwhile, HR leaders are left wondering: where's the AI that actually gets our business? 

At Pinnacle, we're building Pascal, an AI coach that doesn't just understand coaching principles, but understands your company and understands you. Your culture, your challenges,  your role, your interactions, your goals. Creating truly contextual AI coaching that works for everyone from fast-scaling startups to global enterprises is exactly the kind of challenge that gets seasoned HR leaders excited, which is why these three industry veterans were eager to join our journey and help guide Pascal's roadmap while supporting the HR community in building the business case for AI adoption.

That’s why we’re thrilled to welcome: 

- Shelby Wolpa, who has spent the last 20 years building and scaling HR foundations at high-growth companies, including Palantir, One Medical, Instacart, and InVision, all of which reached unicorn or public status during her tenure. As a former People leader who led teams through hypergrowth, she now advises Series A–C startups and scaleups, working closely with CEOs, People leaders, and VC firms to build resilient people operations, design standout employee experiences, and avoid common mistakes. Shelby’s insight will help ensure AI coaching can support the needs of fast, lean, and globally distributed teams.  

- Jeff Diana, a seasoned HR executive and 4x CHRO, with past roles at Calendly and Atlassian, where he helped guide both companies through significant periods of growth. With over 20 years of experience driving organizational transformation, he has held senior HR roles at GE, Microsoft, and Safeco, and was the first CHRO at SuccessFactors, which he took through IPO.  Jeff is passionate about elevating HR as a strategic partner in business transformation, empowering people leaders with the tools, influence, and operational discipline to deliver real impact. He will help guide our roadmap to ensure Pascal continues delivering high value for enterprise HR teams, driving productivity and engagement at scale.

- Barb Bidan, a 3x CHRO, is known for building culture-aligned programs at companies like Crunchyroll, Peloton, Yahoo, Indeed, and InVision, and brings a practical lens to implementing new tools at scale. Barb also champions thoughtful vendor partnerships, seeing external providers as true extensions of the team. She sees AI and automation as key to reducing tactical burdens and enabling HR teams to focus on higher-impact work, with teams that are smaller, more experienced, more cross-functional, and built around adaptable “athletes” who can operate across domains. Her guidance will help ensure Pascal supports this shift. 

"Jeff, Shelby, and Barb get what we're building because they've lived it," said Alexei Dunaway, Founder and CEO of Pinnacle. "They've scaled teams through hypergrowth, navigated massive organizational changes, and know exactly where generic AI tools fall short. Pascal isn't just another coaching platform, it's AI that actually understands context and nuances. Their expertise ensures we're building a solution that's not just powerful, but also scales seamlessly, and drives measurable impact."

The three advisors will work directly with Pinnacle's product and go-to-market teams, ensuring Pascal delivers value whether you're a fast-growth startup or global enterprise managing complexity at scale.