Reflection on impactful individuals at Square

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:

• LinkedIn: https://www.linkedin.com/in/michaelcieri/

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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