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:   / alyssa-henry-0905692  
• Copilot: https://copilot.microsoft.com/
• Gokul Rajaram:   / gokulrajaram1  
• Gusto: https://gusto.com/
• High Output Management: https://amazon.com/High-Output-Manage...
• Marty Cagan:   / 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/capabilities...
• Toast: https://pos.toasttab.com/
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Where to find Michael Cieri:
• LinkedIn:   / michaelcieri  
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Where to find Brett Berson:
• LinkedIn:   / brett-berson-9986094  
• Twitter/X:   / brettberson  
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Where to find First Round Capital:
• Website: https://firstround.com/
• First Round Review: https://review.firstround.com/
• Twitter:   / firstround  
• YouTube:    / @firstroundcapital  
• This podcast on all platforms: https://review.firstround.com/podcast
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Timestamps:
[00:00:00] Introduction
[00:02:41] Why SMBs require unique software solutions
[00:05:58] The level of specificity required when building for SMBs
[00:08:47] Finding Square’s form-fitting solution
[00:11:48] Building vertical versus horizontal SaaS
[00:14:34] Inside Square and Gusto’s decision making framework
[00:16:15] How to build horizontally from a wedge product
[00:23:00] Using the Three Horizons Model
[00:25:29] How to craft a compelling vision for products
[00:28:51] How to assess Horizon 3 bets
[00:32:08] How to give employees the freedom to try things
[00:34:24] Creating a risk-taking culture
[00:37:27] Essential advice for new PMs
[00:40:27] Common thread with bad product pitches
[00:42:29] Applying the Horizon framework at Gusto
[00:44:46] Developing good product sense
[00:47:43] 5 signs of great product sense
[00:49:03] Why product sense is like athletic ability
[00:51:43] How to ship faster without increasing headcount
[00:56:10] People who had an outsized impact on Michael