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.
Timestamps
00:00 – Intro & sponsor
01:00 – The chaos of Superstorm Sandy
02:00 – Anna’s journey: from theater to tech
06:00 – The making of a generalist
10:00 – Joining Cascade and fixing retention
11:00 – Creating a “working rhythm”
14:00 – Governance vs. red tape
17:00 – The 5 pillars of strategic maturity
19:00 – Turning strategy into execution
24:00 – How Cascade uses AI internally
28:00 – OKRs, KPIs, and strategy frameworks
33:00 – Who owns strategy?
36:00 – Rebuilding a business overnight
43:00 – Closing thoughts
Between Two COO's - https://betweentwocoos.com
Episode Website - https://betweentwocoos.com/anna-elwood-coo-cascade
Anna Elwood on LinkedIn - https://www.linkedin.com/in/annaelwood
Michael Koenig on LinkedIn - https://linkedin.com/in/michael-koenig514
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