What does it take for a product-led company to become enterprise-ready?

Kevin Egan · Jul 12, 2023

Striking the balance between end-user love and an enterprise security posture is a really difficult thing to do, and the security/controls work is unsexy but necessary for large companies to trust and expand with you.

Large enterprises will not bring a product in or let it expand unless the security and operational controls are right.

4:57 20Sales: Slack, Atlassian, Dropbox: Five of the Biggest Lessons on Starting, Scaling and Managing Sales Teams from 25 Years Leading the Best with Kevin Egan, Global Head of Enterprise Sales at Atlassian

Sean Murray · Jan 24, 2024

Founders should be able to defend all enterprise compliance and security requirements before attempting to move upmarket

IT gets more senior and more authoritative the further upmarket you go, a data breach is the worst thing that can happen to an enterprise, and most startups lack proof points that they meet compliance requirements

32:55 20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

Raaz Herzberg · Dec 12, 2025

Building enterprise-scale capabilities like role-based access control into the product from day one avoids the common pattern of having to break and rebuild infrastructure later to sell enterprise

Most products bolt these on when they decide to go enterprise and then have to refactor everything

25:09 20Growth: How Wiz Built a $30BN Brand in Enterprise | What Worked vs What Was a Mega Failure: Lessons Learned | Why Marketers Make the Worst CMOs & What To Look for in Growth with Raaz Herzberg

Martin Gontovnikas · Feb 14, 2024

New Relic is the cautionary example: it could have been Datadog but chasing enterprise checklists added product bloat, worsened developer experience, and destroyed its pipeline

Building features to satisfy 200-item RFQ checklists added bloat; when experience degraded developers stopped using it, so no new prospects entered the pipeline even as existing enterprise deals closed

44:19 Chasing enterprise checklists degrades product and kills pipeline

Kevin Egan · Jul 12, 2023

It's naive to treat enterprise readiness as shipping three or four features; there is no finish line — it's a lifelong pursuit in partnership with customers to keep up with the most stringent enterprise requirements.

Requirements keep evolving — e.g. GDPR data requirements are a full-time job to stay compliant with.

9:41 Enterprise readiness is never finished

Des Traynor · Jul 18, 2022

Software companies selling to software companies risk their best customers outgrowing them fast, losing millions in potential revenue for want of small enterprise features

Software companies grow fast and whistle straight through your target segment, and you may be only a few features away from retaining them

30:47 Underinvesting in enterprise features lets fast growing software customers outgrow and churn

Des Traynor · Jul 18, 2022

Moving upmarket requires four immovable product buckets: adaptability, scalability, justifiability and interoperability

Enterprises mandate compliance and SSO, usage scale, data proving delivered value, and being a good citizen of their existing tech stack

36:36 Four pillars adaptability scalability justifiability interoperability define enterprise readiness

Yamini Rangan · Mar 18, 2025

HubSpot was ready to move upmarket into mid-market and enterprise because it was already running its own 4,500-person company on HubSpot, proving product readiness beyond the original ICP

Being customer number zero and running marketing, sales and service on the product at 4,500 employees showed the product already worked well outside the target segment, so the remaining work was strategy, company alignment and the partner ecosystem

22:28 Dogfooding at scale proves enterprise readiness