In this episode of Asking Good Questions, host Edward Roske sits down with Zain Oke, whose career reads like a masterclass in leadership, resilience, and strategic reinvention. From nearly two decades at Deloitte to the boardroom of Daily Harvest, and now leading automotive operations at AAA Northern California, Zain’s journey is a rare blend of financial discipline, operational innovation, and fearless transformation.
The conversation begins with breaking news — Chobani’s acquisition of Daily Harvest — and dives into what it feels like to sit in the room when your company is being bought. Zain shares the inside view of how culture, values, and governance shape such decisions, and how companies can recover trust and rebuild momentum after public crises.
They then explore the evolving relationship between AI and corporate oversight: how boards and audit committees should evaluate AI initiatives, separate game-changers from “expensive toys,” and build risk frameworks that keep innovation safe and accountable. Zain reveals how AI isn’t just reducing costs — it’s unlocking new possibilities for startups and scaling teams by lowering barriers to insight and automation.
The discussion moves to the automotive future: from electric-vehicle repair pilots to the psychological barriers around autonomous cars. Zain candidly reflects on the balance between safety, public trust, and innovation, reminding listeners that AI’s biggest challenge may be the human fear of losing control.
Finally, she offers invaluable advice for finance professionals: how to stay relevant as automation reshapes the CFO’s office, why governance experience is the new gold standard for board readiness, and why learning to “flow through data” is the key skill of the decade.
If you care about finance, AI, corporate transformation, or the next wave of board leadership, this conversation will change how you see the intersection of business and technology.
💬 Quotes & Highlights
“It’s not what happened — it’s what happens next.”
“AI can be a force multiplier, not just a cost reducer.”
“Boards don’t need more retired executives; they need active operators.”
“Fear of losing control is at the heart of resistance to AI.”
“Auditing teaches you how every part of a business actually works.”
“Good information in, good information out — that never changes.”
“We can’t stop what’s been unleashed, but we can help people trust it.”
🕒 Chapter Breakdown
Intro – From Big 4 to Boardrooms (00:00–01:00)
Chobani × Daily Harvest Deal (01:00–03:00)
Recovering from Crisis & Rebuilding Trust (03:00–05:00)
AI in the Boardroom: Guardrails & Governance (05:00–08:00)
The Wellness Economy & Big-Brand Acquisitions (08:00–10:00)
AI’s Impact on Finance & Operations (10:00–13:30)
Digital Transformation in Automotive Services (14:00–17:00)
Career Pivot: From Auditor to Operator (20:00–23:00)
Balancing Board vs Operator Roles (24:00–26:00)
Future of Finance & Automation (27:00–30:00)
How to Join a Board (and Stay Relevant) (31:00–34:00)
Lightning Round + Final Thoughts (34:00–39:00)

This episode of Asking Good Questions is brought to you by Caprus.Ai.
Check how we empower the office of the CFO to harness the transformative potential of artificial intelligence (AI) and revolutionize their operations.