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Tom Whitty
Tom Whitty is Chief Revenue Officer at Upflex, a SaaS platform that gives hybrid and remote employees on-demand access to workspaces around the world. He works with leading organizations to redefine hybrid work and elevate the modern employee experience, bridging flexibility with connection through workspace solutions tailored to today's dynamic workforce.
Making Return-to-Office Something People Actually Want
Tom's core argument is that return-to-office mandates fail for a simple reason: employees can tell when a trip into the office adds nothing they couldn't have done from home. His answer is intentionality, engineering specific in-person moments (onboarding pairings, hackathons, company-wide "power pod" gatherings) rather than mandating undifferentiated days in a building. Upflex has built roughly 30 of these playbook plays with customers, and is now layering AI on top that autonomously reads an organization's collaboration patterns to tell people when and where to show up, and with whom, for it to actually be worth the trip. Before Upflex, Tom spent 15 years in benefits and employee experience sales, including roles at Thrive Global, Limeade, and Willis Towers Watson, and began his career at Liazon, a benefits startup later acquired by Towers Watson.
Topics Tom speaks on
- Why return-to-office mandates backfire, and what works instead
- Engineering intentional in-person moments at scale
- Using AI to match the right people to the right space at the right time
- Connecting flexible work strategy to talent acquisition and retention
- Leading through uncertainty without losing sight of people
Sessions with Achieve
Tom is featured in "The Transform Dialogues Featuring Tom Whitty" (February 2, 2026), an Achieve resource recorded live at the Transform conference in partnership with Engagedly. In it, he discusses why most return-to-office efforts have failed to deliver, how Upflex's "power pod" model creates connection without mandating a fixed office, and his prediction that within three to five years, technology will remove the burden of booking a desk altogether.
Connect
Want more on what it takes to make flexible work actually work for both people and the balance sheet? Learn more about the Achieve Leadership Network.