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Lessons from Gusto & Square on finding your product wedge | Michael Cieri
Manage episode 399909870 series 2815222
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
—
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:
—
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
—
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
137 episodes
Manage episode 399909870 series 2815222
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.
—
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
—
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/
—
Where to find Michael Cieri:
—
Where to find Brett Berson:
- LinkedIn: https://www.linkedin.com/in/brett-berson-9986094/
- Twitter/X: https://twitter.com/brettberson
—
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
—
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
137 episodes
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