Annie Pearl

Chief Product Officer at Calendly

CPO at Calendly, previously CPO at Glassdoor and Director of Product at Fox; board member and member of Skip, a community for chief product officers.

The Operator The Growth Architect

Dimension Profile

Strategic Vision 80%

Execution & Craft 70%

Data & Experimentation 50%

Growth & Distribution 70%

Team & Leadership 60%

User Empathy & Research 70%

Key Themes

product strategy as integrated choices where to play and how to win PLG and product-led growth scheduling product dynamics market segmentation product leadership career path

Episode Summary

Annie Pearl shares her approach to product strategy as an integrated set of choices about where to play and how to win, drawing from her experience leading product at Calendly, Glassdoor, and Fox. She discusses the dynamics of building a product-led growth scheduling tool, the importance of reducing friction for all parties, and how product leaders should think about market segmentation and persona targeting.

Leadership Principles

→ Strategy is an integrated set of choices that outline how you're going to win in your chosen marketplace
→ A good product strategy answers: winning aspiration, where to play, segments, personas, and how to win
→ Product leaders must be willing to make hard choices about where NOT to play

Notable Quotes

"Strategy is really just an integrated set of choices that outline how you're going to win in whatever marketplace you choose. A good product strategy answers: what's your winning aspiration, where are you going to play, what are the personas, and how are you going to win?"
— On defining product strategy simply and clearly

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