Sessions
Prove the Impact: ROI, Business Cases, and Winning Leadership Buy-In

November 11, 2026

Tamara Sheehan is the Director of Global People Operations at Rain, the AI financial health platform that has paid out over $6 billion in earned wages to 4 million employees across 1,800 employers. At Rain, Tamara owns the people operations function end-to-end — HR tech stack, compensation (both cash and equity), compliance, benefits, and people data — and has spent more than two decades building people operations that function as genuine business partners rather than back-office support, using workforce and engagement data to shape decisions on compensation strategy, benefits design, and organizational structure, and to make the case to executives for where and why to invest in their people. That data-driven, business-first approach has been tested across some of the most consequential moments a people leader faces: guiding two companies (SpaceIQ, acquired by WeWork, and ChooChee, acquired by Deutsche Telekom) through acquisition due diligence and post-close integration, and managing global compliance and people operations for a multi-country workforce today. Tamara also spent several years as an independent People Operations and Business Management consultant, advising startup leadership teams on how to use workforce data to close the gap between where their people programs were and where their business needed them to be. She brings that same lens to conversations about proving the ROI of people programs: engagement and workforce data aren't just reporting tools — they're how you build the business case that earns leadership's continued trust and investment.

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