Nickey Skarstad (Airbnb, Etsy, Shopify, Duolingo) on translating vision into goals, operationalizing product quality, second-order decisions, brainstorming, influence, and much more
July 18, 2022
AI Summary
5 min readNickey Skarstad, a director of product at Duolingo with prior roles at Etsy, Airbnb, Shopify, and The Wing, shares principles for turning high-level vision into execution, emphasizing product quality, decision frameworks, and team alignment.
Vision, Strategy, and Goals
Skarstad uses a vision-mission-strategy-objectives pyramid to cascade long-term aspirations into quarterly OKRs. She starts with cross-functional brainstorms in tools like Miro or FigJam, prompting teams on 10-year horizons, competitive landscapes, and past experiences (e.g., memorable travel moments for Airbnb Experiences). Synthesis follows in the session, with the leader drafting and iterating for buy-in. OKRs articulate strategy concretely for the next 3-6 months, reviewed quarterly with leadership, ensuring features ladder up without democratic voting—strategy requires a clear owner.
Product Quality Metrics and Practices
Quality balances growth via metrics like Airbnb Experiences' review rate (prioritizing 5-star experiences over bookings) and Etsy's first-sale-in-7-days (adding onboarding friction to boost seller success). Operationalize through host coaching, dogfooding (team uses the product firsthand), and Slack feedback loops. Avoid shipping imperfect features; obsess over end-user experience, edge cases, and second-order effects to prevent downstream rework.
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What you'll learn
- 1 **[00:00-05:00] Career Journey and Entry into Product**
- 2 **[05:30-14:00] Airbnb Experiences: Achieving PMF and Product Quality**
- 3 **[14:30-17:00] Post-Airbnb Moves: Startups, Shopify, Duolingo**
- 4 **[17:30-25:00] Role Fit, Energy Audit, and Product Org Structures**
- 5 **[27:30-36:00] Translating Vision to Goals: Pyramid Framework**
- 6 **[36:30-47:00] Decision-Making, Second-Order Thinking, and Alignment**
- 7 **[47:30-54:00] Execution: Kickoffs, Reviews, and Staying Aligned**
+ Full timestamped outline available in the app
Show Notes
Nickey Skarstad is a Director of Product Management at Duolingo, where she is leading a stealth 0 → 1 product. Prior to Duolingo, she was VP of Product at The Wing, Product Lead at Airbnb, where she led much of the Experiences product team, Product Lead at Shopify, and Director of Product Management at Etsy.
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Thank you to our wonderful sponsors for making this episode possible:
• Mixpanel: https://mixpanel.com/startups
• Dovetail: https://dovetailapp.com/lenny
• Unit: https://unit.co/lenny
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In this episode:
[3:32] An overview of Nickey’s career
[7:39] What she learned from building product at Airbnb
[8:42] How to maintain and operationalize product quality
[9:44] Metrics that help you maintain quality
[20:08] Which company has most informed her product development approach
[21:57] How to structure your product org
[24:47] Should you go GM vs. functional
[27:18] How you set vision, translate that into goals, and then execute on it
[32:30] Brainstorming advice
[35:04] How to use OKRs effectively
[37:57] How to get better at influence as a PM
[41:23] How to know if a decision is a one-way or two-way door
[42:29] Second-order decisions, and second-order thinking
[46:35] Operationalizing principles
[47:17] Getting your team on board with your strategy
[49:39] Designing a product review meeting
[54:08] Tips for working remotely as a PM
[56:44] Lightning round
—Find the full transcript at: https://www.lennysnewsletter.com/p/nickey-skarstad-airbnb-etsy-shopify—
Where to find Nickey:
• Newsletter: https://nickey.substack.com/
• TikTok: https://www.tiktok.com/@nickeyskarstad
• LinkedIn: https://www.linkedin.com/in/nickeyskarstad/
• Twitter: https://twitter.com/NickeySkarstad
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Referenced:
• Thinking in Systems by Donella H. Meadows
• More from this podcast