Part 1: Catherine Stewart on Scaling Operations and People Management at Shippo and Automattic

Catherine Stewart is the former Chief Operating Officer at Shippo and Chief Business Officer at Automattic (WordPress),  joins us in part one of a special two-parter, to talk about the craft of scaling operations at hyper-growth tech companies. Topics include shifting strategic priorities at Automattic to also focus on revenue generation and e-commerce through the acquisition of WooCommerce, the shift from Facebook to Automattic, balancing the entrepreneurial mindset with the need for processes, not sugar-coating it, and why her time at Random House yielded some of the most valuable learnings of her career.

Part two, coming next month, focuses on scaling the go-to-market and creating $B's in value.

Shippo is a shipping software company backed by Bessemer and D1, where she led Marketing, Sales, Business Development, Customer Success, Customer Support, People Ops, and Strategic Planning. During her time at the company, Shippo's revenue grew 3x faster than the US eCommerce shipping market, and the company's valuation grew from $220M to over $1B in just 18 months.

Prior to joining Shippo, Catherine was the Chief Business Officer at Automattic, the company behind WordPress.com, during the company’s growth from a valuation of $1B to $3B. While at the company, she led the acquisition and integration of WooCommerce. Previously at Facebook, she helped launch the Facebook Audience Network and led the three-year planning process, and at Random House, worked on the transition from physical to digital books. Catherine began her career as a strategy consultant at McKinsey.

Stay up to date with Catherine at:

• LinkedIn: https://www.linkedin.com/in/catherine-stewart-800b841/
• Website: https://catherinetaylorstewart.com
• Episode Webpage: https://www.betweentwocoos.com/catherine-stewart-part-one-people

Stay up to date with Michael at:  https://linkedin.com/in/mkoenig514