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The 250,000 Customer Club: How HubSpot and Monday.com Both Created SMB+ Empires

SaaStr

Both started SMB (Monday even more so), and Both have now gone more enterprise (Monday even more) But still with the vast majority of their customers SMB. Enterprise Expansion : While maintaining strong SMB growth, Monday.com has successfully moved upmarket. To Focus on Tech Or Not?

SMB 273
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Scaling 6 Products to $100M+ ARR Each: Samsara’s CPO Kiren Sekar on Multi-Product Growth

SaaStr

Cross-Vertical Market Expansion Creates Unexpected Innovation Synergies While many startups laser-focus on dominating a single vertical, Sekar’s experience at both Meraki and Samsara showed that deliberate cross-vertical expansion creates powerful network effects of innovation.

Scale 260
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The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

SaaStr

At least for SMB and more routine mid-market sales. Organizations clinging to traditional sales structures especially in SMB and mid-marklet will find themselves rapidly outpaced by competitors embracing this hybrid approach. But you can automate 30%-40% of support for real … with top 10% CSAT. A 50/50 Sales Team. 50% are AI.

Scale 236
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Top SaaStr Content for the Week: Gorgias CEO, Postman CEO, Waze Head of SMB Sales, Klaviyo SVP Marketing, and More!

SaaStr

SaaStr 527: Acquiring 10,000 SMB Customers Solely from Data with Gorgias CEO Romain Lapeyre. The 4 V’s of Sales: Volume, Value, and Velocity with Waze Head of SMB Sales Fernando Belfort and Head of Sales Enablement Kendra Wrightson. How To Innovate Faster with Community: Insights From GitLab CEO Sid Sijbrandij.

SMB 283
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The Innovator's Dilemma for SaaS Startups

Tom Tunguz

See also: Innovator’s Solution for SaaS Startups. There’s a familiar path now to SaaS companies that start in the SMB (small-to-medium business) part of the market. I believe we’re seeing Clay Christensen’s Innovator’s Dilemma at play. SMB 3-7% 31%-58%. Why does this happen? Enterprise 0.5-1%

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Top 10 Reasons SaaStr Annual 2025 Will Be Better Than Ever!! May 13-15 in SF Bay!

SaaStr

150+ Sponsors Driving Innovation From the biggest names in cloud to the most exciting startups, our 150+ sponsors are showcasing the latest innovations in SaaS and AI. VIP Summits for Every Role Weve expanded our VIP events to include summits for CROs, CMOs, CFOs, and CCOs. And networking.

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The Enterprise Journey: 8 Keys to Going Upmarket Successfully with Workiva’s CEO Julie Iskow

SaaStr

Look for an innovative enterprise customer who: Is willing to be a development partner Has clear needs you can solve today Will give you access to testing environments Can help shape your roadmap The goal isn’t to build custom features – it’s to deeply understand enterprise requirements and bake them into your core product.