Oliver Jay is a sales and expansion specialist. Oliver was Chief Revenue Officer at Asana and led the company’s global expansion. He grew the team from 20 to 450 people and increased international income to 40% of Asana’s total revenue. Prior to this, Oliver built the first business sales team at Dropbox, and led the company’s expansion into the Asia-Pacific region while tripling ARR. Oliver is now an advisor and leadership coach focused on assisting founders and executives in scaling their businesses.

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In today’s episode, we discuss:

• Common mistakes PLG companies make
• The “PLG trap” and how to avoid it
• The playbook for transitioning into enterprise
• How and when to build an enterprise sales team
• How PLG companies can break $10 billion market cap
• Why it’s difficult to emulate Atlassian, Slack or Salesforce

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Referenced:

• Airtable: https://www.airtable.com/
• Asana: https://asana.com/
• Atlassian: https://www.atlassian.com/
• Bitbucket: https://bitbucket.org/product/
• Confluent: https://www.confluent.io/
• Daniel Shapero: https://www.linkedin.com/in/dshapero/
• Datadog: https://www.datadoghq.com/
• Dennis Woodside: https://www.linkedin.com/in/dennis-woodside-341302/
• Dropbox: https://www.dropbox.com/
• Dustin Moskovitz: https://www.linkedin.com/in/dmoskov/
• Jay Simons: https://www.linkedin.com/in/jaysimons/
• Jira: https://www.atlassian.com/software/jira
• Justin Rosenstein: https://www.linkedin.com/in/justinrosenstein/
• Kim Scott: https://www.linkedin.com/in/kimm4/
• Salesforce: https://www.salesforce.com/
• Slack: https://slack.com/
• The PLG Trap: https://www.linkedin.com/pulse/plg-trap-oliver-jay/
• The seed, land, and expand framework: https://www.endgame.io/blog/seed-land-expand-framework
• Zendesk: https://www.zendesk.com/

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Where to find Oliver Jay:

• LinkedIn: https://www.linkedin.com/in/oliverjayleadership/
• Website: https://www.oliverjayleadership.com/

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Where to find Brett Berson:

• Twitter/X: https://twitter.com/brettberson
• LinkedIn: https://www.linkedin.com/in/brett-berson-9986094

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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

(02:23) Differences between PLG and enterprise companies

(05:56) Avoiding the “PLG trap”

(07:39) Transitioning to enterprise feels like building two companies

(10:57) Thinking about user value versus company value

(13:58) The relationship between OKRs and executive champions

(14:59) Dropbox had almost no company value

(15:33) The strategy PLG companies should avoid

(18:30) Why Dropbox is worth $10b, not $50b

(19:41) The story of Asana’s expansion

(21:16) Asana’s unique customer success team

(23:27) How product strategy relates to finding champions

(25:03) How Asana structured its GTM org

(27:11) What Oliver would have done differently with Asana’s GTM

(29:45) Getting executive-level buy-in

(31:49) Asana’s concept of “selling clarity”

(33:18) An inside look at Asana’s transition into enterprise

(37:59) The champion tree framework

(40:43) Structuring Asana’s early enterprise sales team

(44:27) The impact of company size on GTM

(47:20) Common sales mistake

(48:29) The seed, land, and expand framework

(51:43) Oliver’s advice to founders

(54:13) Why building horizontally may be a mistake

(55:32) Common challenges faced by PLG companies

(58:30) How PLG companies can break the $10b market cap

(60:17) Why emulating Atlassian’s playbook is difficult

(63:21) People who had an outsized impact on Oliver