Anna Elwood is a seasoned operations and strategy leader currently serving as Chief Operating Officer at Cascade. In this role, she leads post sales and various G&A efforts. Since joining Cascade, she’s transitioned the company to a hybrid work model with hubs in NYC and Sydney, strengthened product‑customer feedback loops, product adoption and improvements in retention and business performance predictability and cultivated a high-performing, team-oriented culture.

Before Cascade, Anna held key leadership positions across high‑growth companies:

VP of Operations at Zocdoc (employee #17): She scaled operations during Zocdoc’s transformation into a unicorn, building, scaling and evolving post sales teams and systems across multiple markets and growing the team from a startup to 600+ employees.

SVP of Revenue at Teachable: Led go-to-market and revenue teams that achieved over 100% growth, including and following the $250m acquisition by Hotmart, and was a key leader in the development, alignment, management and execution of strategy.