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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.

SMB 273
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Approaching Half a Million Customers: How to Win in SMB with BILL CEO and Founder René Lacerte

SaaStr

SMB Unit Economics: Why Is 6 Quarters the Right Target for SMBs at Scale? So, SMBs are asking for consolidation, and that’s why Bill has acquired companies and continues to add more financial operation capabilities. BILL wants to be at the heart of every SMB business. If we go back to 2006, BILL was a cloud-based company.

SMB 307
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What Really Works When Hiring VPs and Executive Teams with HubSpot Co-Founder and Chairman Brian Halligan and SaaStr CEO and Founder Jason Lemkin

SaaStr

The Current State of Leadership Tenures in SaaS Brian sets the stage frankly on how hiring has gone at HubSpot: “We’ve hired a lot of executives, but many haven’t worked out.” Our head of product, head of engineering, like pretty much everybody in leadership. They grew up in their career with us.

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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. ” This represents perhaps the greatest leadership change of the coming year. Organizations clinging to traditional sales structures especially in SMB and mid-marklet will find themselves rapidly outpaced by competitors embracing this hybrid approach. A 50/50 Sales Team.

Scale 236
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How Salesforce Runs Its Internal Forecasting Process with Salesforce’s VP Sales Strategy & Programs and RVP SMB Sales

SaaStr

During SaaStr Annual , Eric Huff, VP of Sales Strategy and Programs, and Theresa Stevens, Regional VP of the SMB sales team, shared an “under the hood” look at how Salesforce does its internal forecasting using Salesforce. At the same time, AE’s are expected to go in and update opportunities. Don’t just drive a weekly cadence.

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5 Interesting Learnings From Monday at $1.125 Billion in ARR

SaaStr

The company is successfully evolving from its SMB roots into a serious enterprise software contender. The ability to maintain NDR above 110% at this scale from a still primarily SMB base proves their land-and-expand model continues to work effectively and customers find ongoing value in the platform.

Scale 189
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Secrets to SMB at Scale with Hubspot CEO Yamini Rangan and SaaStr Founder & CEO Jason Lemkin (Pod 616 + Video)

SaaStr

Yamini Rangan, CEO at HubSpot, has many insights on how to serve SMB customers at scale. The Challenge of Digital Expansion for SMB. When the shift began in 2020, everyone wrote off SMBs as unprepared for the necessary changes that lie ahead. The past few years have kicked off an unprecedented wave of digital expansion.

Scale 261