Between Two COO's with Michael Koenig

Peter Dougherty, President of Spreedly, breaks down how payments are changing, why “open payments” is the new orchestration, and how AI and agentic systems will reshape commerce at a structural level. We talk scaling from 20M to 100M, building teams for inflection points, finding existential problems vs noise, and why perception is often more important than raw numbers. We also cover fraud, Spreedly’s acquisition of Dodgeball, and what agent to agent payments unlock in the next decade.

Show Notes

This episode goes deep into the mechanics of scaling a company from steady growth to breakout velocity. Peter shares how Spreedly quadrupled ARR growth in his first year without increasing OPEX, why the “right people pointed at the right problems” is everything, and how to decide which problems are existential versus learn-as-you-go.

We dissect how go-to-market organizations evolve from $20M to $100M ARR, the power of focus and role separation, and how to keep silos aligned around one customer story.

Peter also explains the shift from “payments orchestration” to “open payments” and how Spreedly’s position as the original player in the space gives them unique leverage. We walk through the future of agentic commerce, Google’s new agent-to-agent payments protocol, and what it means when agents can transact faster than any human could ever shop.

We close out with the Dodgeball acquisition, a primer on fraud orchestration, and a wild story about working an entire night shift at a nightclub during a meltdown launch.

Topics Covered:

  • How Peter defines the journey to presidency
  • The “right person, right problem” framework
  • One-way vs two-way doors for staffing big problems
  • How to scale a GTM org from $20M to $100M
  • Why open payments replaces orchestration
  • Spreedly’s unique market position and 15-year head start
  • Agent to agent commerce and Google’s new payments protocol
  • How AI changes the velocity of money movement
  • Fraud orchestration and Spreedly’s acquisition of Dodgeball
  • Balancing profitable growth vs growth at all costs
  • Perception vs reality in leadership
  • Peter’s wildest “I never thought I’d see that” story

 

What is Between Two COO's with Michael Koenig?

Between Two COOs is hosted by veteran COO Michael Koenig and brings together Chief Operating Officers, executives, and business leaders to share real insights on operations, leadership, scaling, AI, and execution. Featuring COOs from companies like LVMH, Vodafone, Automattic, Lime, JumpCloud, Grafana Labs, and Cotopaxi, plus top VCs like Brad Feld and Seth Levine. Whether you're a COO, VP of Ops, founder, or aspiring operator — this is the podcast for people who actually run companies. New episodes weekly. betweentwocoos.com | b2coos.com