Michael Cieri is the Chief Product Officer at Gusto, an HR and payroll platform used by more than 300,000 businesses. With a decade of experience, he has led successful SMB product development and scaled high-performing orgs. Before Gusto, Michael was also the Head of Product at Square, where he led a team of 15+ PMs responsible for $600m in annual revenue. Michael was also the VP of Product Management at Opendoor.
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In today’s episode, we discuss:
- Key product strategies used by Square and Gusto
- The pros and cons of building for SMBs
- How to build horizontal after creating a wedge
- The catch with building vertical SaaS
- How product teams can move faster
- Developing product sense and intuition
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Referenced:
- Alyssa Henry: https://www.linkedin.com/in/alyssa-henry-0905692/
- Copilot: https://copilot.microsoft.com/
- Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/
- Gusto: https://gusto.com/
- High Output Management: https://amazon.com/High-Output-Management-Andrew-Grove/dp/0679762884
- Marty Cagan: https://www.linkedin.com/in/cagan/
- Opendoor: https://www.opendoor.com/
- Silicon Valley Product Group: https://www.svpg.com/
- Square: https://squareup.com/
- The Three Horizons Model: https://www.mckinsey.com/enduring-ideas-the-three-horizons-of-growth
- Toast: https://pos.toasttab.com/
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Where to find Michael Cieri:
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Where to find Brett Berson:
- LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
- Twitter/X: https://twitter.com/brettberson
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Where to find First Round Capital:
- Website: https://firstround.com/
- First Round Review: https://review.firstround.com/
- Twitter: https://twitter.com/firstround
- YouTube: https://www.youtube.com/@FirstRoundCapital
- This podcast on all platforms: https://review.firstround.com/podcast
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Timestamps:
(00:00) Introduction
(02:41) Why SMBs require unique software solutions
(05:58) The level of specificity required when building for SMBs
(08:47) Finding Square’s form-fitting solution
(11:48) Building vertical versus horizontal SaaS
(14:34) Inside Square and Gusto’s decision making framework
(16:15) How to build horizontally from a wedge product
(23:00) Using the Three Horizons Model
(25:29) How to craft a compelling vision for products
(28:51) How to assess Horizon 3 bets
(32:08) How to give employees the freedom to try things
(34:24) Creating a risk-taking culture
(37:27) Essential advice for new PMs
(40:27) Common thread with bad product pitches
(42:29) Applying the Horizon framework at Gusto
(44:46) Developing good product sense
(47:43) 5 signs of great product sense
(49:03) Why product sense is like athletic ability
(51:43) How to ship faster without increasing headcount
(56:10) People who had an outsized impact on Michael