In this episode of Tank Talks, host Matt Cohen sits down with Wayne Pommen, Chief Revenue Officer at Affirm and founder of PayBright, Canada’s first e-commerce buy now, pay later platform. Wayne shares his unlikely journey from competitive rowing, including the Oxford-Cambridge Boat Race, to a PhD in international relations, Bain Consulting, and private equity at TorQuest, where a failed deal set him on the path to building a fintech unicorn.

Wayne pulls back the curtain on PayBright’s early days, from spinning out a tiny 5-person division called HealthSmart Financial Services to pivoting into e-commerce and landing Casper and Endy as launch partners. He offers a practical breakdown of running a successful M&A process, sharing the dos and don’ts that led to Affirm’s acquisition of PayBright in 2020.

Now a senior executive at a public fintech giant, Wayne reflects on what he’s learned from working alongside Max Levchin, why Affirm refuses to charge late fees or deferred interest, and how AI is transforming everything from underwriting to go-to-market. He also shares his views on agentic commerce, the Canadian consumer credit landscape, and why “don’t quit” is his favorite life lesson.

Whether you’re a founder navigating a pivot, an operator scaling through acquisition, or just curious about the future of payments and AI, Wayne Pommen delivers the kind of straight talk that comes from building and scaling one of Canada’s most successful fintech stories.

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From Cambridge to Bain to Private Equity (03:10)

* The Oxford-Cambridge Boat Race, a broken wrist, and a comeback story

* Why he chose Bain over academia and how consulting shaped his career

* Joining TorQuest and zeroing in on non-bank financial services

Finding the Kernel: HealthSmart Financial Services (05:18)

* The summer of 2013, losing a deal but falling in love with the point-of-sale lending model

* Why banks ignored this niche and how technology was changing the game

* Spinning out a tiny five-person division with no CEO

The Pivot to E-Commerce (10:14)

* Doubling the health business in 2016 and realizing it would take forever

* The epiphany: Canada had no point-of-sale financing for e-commerce

* Mapping out the user experience over Christmas 2016 and pre-selling Casper and Endy

Building PayBright: Scrappy, Fast, and Capital Efficient (15:00)

* Running a “double-headed monster,” healthcare and e-commerce side by side

* Advice for founders navigating platform shifts, from legacy platforms to AI-native products

* The economics of buy now, pay later, merchant fees, interest rates, and cost of risk

The Affirm Acquisition (21:02)

* Growing annual loan volume from $6 million to $220 million in five years

* The COVID boom and inbound interest from Klarna, RBC, TD, and Affirm

* Running a mini process, dos and don’ts for founders

Staying On: Becoming CRO at Affirm (27:34)

* Why he stayed past the earnout and has now been there for more than three years

* Lessons from Max Levchin and the “dog on a bone” approach to going deeper

* How to stay focused across multiple products and jurisdictions

Agentic Commerce and the Future of Shopping (33:09)

* What agentic commerce really means and what it doesn’t

* Why agents will read the fine print and guide consumers to better choices

* The partnerships with Google, Stripe, and Shopify

Banning Deferred Interest and Late Fees (36:04)

* Why deferred interest is “borderline abusive” and hard to defend

* Affirm’s no-late-fee, no-compounding, transaction-level underwriting model

* Aligning lender and consumer interests, the Max Levchin insight

From Private to Public: Lessons in Discipline (40:32)

* How being public forces discipline without over-dictating the quarter

* Advice for CROs on timing the public markets

* Why Stripe staying private proves there’s no one-size-fits-all path

AI at Affirm: Supercharging Revenue and Underwriting (44:11)

* The proliferation of AI tools internally and the excitement of experimentation

* How transformer-based models are improving underwriting

* The future of work, querying Slack for tribal knowledge in seconds

About Wayne Pommen

Wayne Pommen is Chief Revenue Officer at Affirm, where he oversees the company’s revenue-generating teams and products. He joined Affirm in January 2021 through its acquisition of PayBright, Canada’s leading buy now, pay later provider, which he founded and led as President and CEO starting in 2015, growing it from 5 to 250 employees with retail partners including Apple, Hudson’s Bay, Wayfair, Samsung, and Sephora. Before PayBright, Wayne was a Principal at TorQuest Partners and a consultant at Bain & Company. A former competitive rower for Canada’s national team, he holds a degree from Harvard and a PhD from Cambridge.

Connect with Wayne Pommen on LinkedIn: https://www.linkedin.com/in/wayne-pommen-8844021/

Visit Affirm’s website: https://www.affirm.com/

Connect with Matt Cohen on LinkedIn: https://ca.linkedin.com/in/matt-cohen1

Visit the Ripple Ventures website: https://www.rippleventures.com/

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit tanktalks.substack.com

How “Buy Now, Pay Later” Really Works with Wayne Pommen of Affirm

Tank Talks By Ripple Ventures

How “Buy Now, Pay Later” Really Works with Wayne Pommen of Affirm