The COO Who Turns Chaos Into Clarity - Anna Elwood of Cascade

From Zocdoc to Cascade, COO Anna Elwood breaks down the systems, rhythms, and AI tools that turn chaos into execution. In this episode of Between Two COOs, Michael sits down with Anna Elwood, COO of Cascade, the strategy-execution platform helping companies turn plans into results.Anna shares how she evolved from Broadway actor to operator, scaling companies like Zocdoc, Knotel, and Teachable before joining Cascade to build the muscle of strategy execution. She explains how to create an “operating rhythm” that keeps teams aligned across time zones, the tension between governance and red tape, and how Cascade helps leaders link vision to measurable execution.The conversation dives deep into AI’s role in operations, the future of hybrid work, and what it takes to move from chaos to clarity in a global startup. Anna’s storytelling — especially her account of leading through Superstorm Sandy — highlights what real-time operational leadership looks like when everything goes sideways. Timestamps00:00 – Intro & sponsor01:00 – The chaos of Superstorm Sandy02:00 – Anna’s journey: from theater to tech06:00 – The making of a generalist10:00 – Joining Cascade and fixing retention11:00 – Creating a “working rhythm”14:00 – Governance vs. red tape17:00 – The 5 pillars of strategic maturity19:00 – Turning strategy into execution24:00 – How Cascade uses AI internally28:00 – OKRs, KPIs, and strategy frameworks33:00 – Who owns strategy?36:00 – Rebuilding a business overnight43:00 – Closing thoughts Between Two COO's - https://betweentwocoos.com Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascadeAnna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwoodMichael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514