The AI Mandate for Finance Leaders (from Chewy's CAO) episode artwork

EPISODE · May 13, 2026 · 1H

The AI Mandate for Finance Leaders (from Chewy's CAO)

from Breakthrough Work Podcast · host Connor Group

Join us as Will Billings, CAO and Treasurer at Chewy, walks through a finance career built across six industries, two public company boards, and one of the most-cited pandemic RIFs in tech history. Topics covered:The three foundational lessons from Big Four audit that still govern how he leads (2:22)Why he left audit for industry, and the shift from validating to building (8:47)Joining GE and the move from leading teams to influencing leaders without formal authority (11:18)The 90-day listening rule he runs every time he enters a new finance seat (15:46)Elevation, not elimination: his blueprint for AI in finance, clean data architecture, and the future of the record-to-report function (18:17)What the Big Four's campus hiring cuts mean for your 2030 Senior Accountant bench, and the internal rotation program he's building at Chewy in response (19:33)Pursuing public company board service during an active operator career, and how to get recruited onto your first board (28:32)The operator-to-director mindset shift, and what board service taught him about running his finance team (35:56)Going back for his MBA mid-career, and the family essay that got him in (39:11)Leading Airbnb's 25% RIF in April 2020, the public pitch book that helped impacted employees land, and why clarity and empathy coexist (47:04)The back injury that rewrote his view of resilience, and the workout routine that kept him steady (50:46)The one equation Will wishes he'd learned a decade earlier (57:29)Will's career spans EY, oilfield services in Houston, GE's industrial portfolio, Airbnb, Global Foundries, Chewy, and public board seats at Sucro and an autonomous security robotics company. For CFOs, Controllers, finance VPs, and aspiring accounting executives, this conversation is a working manual for scaling finance teams across industries, cycles, and the AI transition.

Episode metadata supplied by the publisher feed · Published May 13, 2026

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