About
Between Two COO's is a podcast about how companies actually run. The people in the chair are COOs, chiefs of staff, VPs of ops, the operators who turn strategy into execution every day. The job is mostly hidden, situational, and learned the hard way. The show exists to make it less hidden.
Hosted by Michael Koenig, a three-time public and private company COO, the show brings on operators from companies like Google, LVMH, GitLab, Webflow, and Techstars for candid conversations about what it really takes to run a business.
No scripted talking points. No surface-level advice. Operators talking to an operator about the frameworks, the mistakes, and the lessons that actually changed how they work.
About Michael Koenig
Michael Koenig has spent over twenty years running operations at public and private companies across SaaS, e-commerce, media, and technology.
He's been COO three times. At Lunar Labs, a consumer mobile company that rebranded as Sweet and moved into B2B OSS and BSS software. At Time Doctor, a time tracking and HR performance management company, where he ran every division. And at Tucows, the publicly traded internet services company. Before becoming COO at Tucows he served as Chief Revenue Officer at Wavelo, the Tucows subsidiary.
He spent six years at Automattic, the company behind WordPress, helping it grow to a multi-billion-dollar valuation. He joined Automattic through the acquisition of Intense Debate, a company that went through the first Techstars class in Boulder in 2007 and became Techstars' first exit.
Across those roles he's owned P&L, revenue operations, product, engineering, and go-to-market, in companies ranging from early-stage startups to publicly traded enterprises. He has also served on company boards, and as an advisor and angel investor to other operators and founders.
He now runs Helm, an execution intelligence system that tells leadership teams whether they're going to hit their goals, where execution is drifting, and what to do about it while there's still time, with AI doing the hard parts.
He started Between Two COO's because the COO role is one of the most important and least understood jobs in business. Every company runs differently, every COO operates differently, and the only way to learn the job is from the people doing it.
Connect with Michael on LinkedIn →
Featured On
- Second in Command with Cameron Herold, Ep. 191: Time Doctor COO, Michael Koenig
- Lead the Team, The Guardrails Came Off! Leading in the Age of AI: COO Tucows, Michael Koenig
What We Cover
- How COOs structure their operating rhythms and weekly cadences
- Scaling operations from Series A through IPO
- AI in operations, and what it changes about the COO role
- Managing cross-functional dependencies and organizational alignment
- Building and leading executive teams
- Crisis management, from operators who've lived it
- The relationship between the CEO and COO
- M&A integration, fundraising operations, and board management
- Hiring, firing, and building teams that perform
Where to Listen
🎧 Apple Podcasts
🎵 Spotify
▶ YouTube
Get in Touch
For guest inquiries, sponsorship, or just to say hello: