Between Two COO's

Today, Michael Koenig, our host and founder of Between Two COO's, shared something deeply personal about what it means to “arrive.” One year ago, he stepped away from his role as COO of a public company and took a true pause. Four months offline. Fifteen projects turned down. Twelve family trips. What started as rest became a reset. “I realized resilience isn’t endurance. It’s design - a life that doesn’t break you first.” Last week, he spoke about this on stage at Operations Nation in London - to a room full of operators and COOs - exploring how titles can become identities and calendars can become cages. The message resonated with many of us who’ve lived the same cycle of achievement and exhaustion. As operators, we design systems for others every day. But how often do we design our own lives with the same intention? We’d love to hear from the community: What have you learned to set down so you can show up fully - at work and in life?

What do you do when your entire company goes dark overnight? In 2012, Superstorm Sandy hit New York and shut down Zocdoc’s headquarters. Anna Elwood, now COO of Cascade, was in Scottsdale, and within 24 hours, she rebuilt the company’s operations out of a Sheraton ballroom in Times Square. It’s one of the wildest real-world leadership stories I’ve heard. 🎥 Watch the clip from our conversation on Between Two COO's and check out the full interview at b2coo.com

Our first-ever video episode is live on YouTube! 🎥 And we couldn’t have kicked it off with a better guest than Anna Elwood, COO of Cascade — the strategy execution platform helping thousands of teams turn plans into results. In this episode, Anna shares what it takes to actually execute strategy, how to build a company’s “working rhythm,” and how to balance governance and speed. We also dive into how AI is changing operations and the COO role — plus Anna’s wild story of rebuilding Zocdoc’s headquarters overnight during Superstorm Sandy. It’s an incredible conversation about leadership, resilience, and building clarity in the middle of chaos. 🎥 Watch on YouTube: https://lnkd.in/gzggXPf8 🎧 Listen wherever you get your podcasts: https://lnkd.in/gfE5cMqe

Lance Willett made a $250,000 mistake—and it became one of the defining leadership lessons of his career. Today, he’s Chief Quality Officer at Automattic, helping power 45% of the internet through WordPress.com, WooCommerce, and Tumblr. In this episode of Between Two COO's, we unpack what it means to own quality at global scale—and what happens when things break. We get into: • How Lance recovered from that mistake and what Matt Mullenweg said when it happened • The overlooked power of technical operations in growth and retention • Automattic’s real-world use of AI—from deflecting support tickets to building entire websites • What “quality” actually means across 2,000+ repos and billions of users • How to manage ambition without burning out your team—or your infrastructure This one’s a masterclass in operating at scale, owning your mistakes, and building systems that hold up under pressure. Link in comments.

So many great guests coming up, it’s hard to decide which one we’re most excited for. Oh wait, it isn’t! We’re excited about all of them!

This whole thing started because I wanted to stop Googling ’how to be a COO.’ There’s no playbook for ops. Just a lot of asking questions, duct tape, team therapy, and hoping your CEO doesn’t slack you at 11pm with “quick question?” So I started Between Two COO's — partly to learn, partly as therapy, and partly because I wanted better answers than what I was getting from Google. Fast forward: I now get to sit down with people I’d normally be DM’ing for advice, and there are some extraordinary guests coming up: • Wade Foster, CEO at Zapier • Brad Feld, Investor at Foundry and Author • Susan K., Operations at Abnormal AI • Lance Willett, Chief Quality Officer at Automattic • Gregory Keller, CTO at JumpCloud • Anna Elwood, COO at Cascade • Zulema Quintans, COO at Noda • Harris Clarke, COO at GUIDEcx • Lindsey Scrase, COO at Checkr, Inc. It’s still a side project. Still takes 7-10+ hours per episode. But I learn something every single time. And if you’re in the ops seat — or thinking about it — these convos might save you a few years of pain. Follow along so you don't miss an episode.

So often, we dismiss ideas for new products and companies because they lack scale and won’t become unicorns. There’s nothing wrong with building a really great horse — who knows, it might win big races.

So does this mean that pretty soon Between Two COOs interviews will be done by AI? 😆

When Linda Tong talks, I listen, and so should you. She isn’t speculating on how to lead as CEO through AI disruption—she’s doing it. From AppDynamics to Webflow, she’s built and led at the highest levels in tech. In this episode, we go deep on: • The future of the web (hint: it’s not just SEO anymore—it’s AEO and dual-site strategies for agents + humans) • How Linda runs ops like a product, using EV (expected value) thinking and stack-ranked bets across G&A, GTM, and R&D • Tactical frameworks for unlocking innovation and psychological safety • What actually happened inside Webflow during the SVB bank collapse Linda isn’t guessing. She’s done this at scale—at two iconic companies. This is one of my longer episodes, and I'm glad we blew past the usual time limit. Thanks for being so generous with your time, Linda! If you’re a founder, operator, or future CEO, you’ll want this one in your feed. Links to the episode are in the comments.