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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. Bottom-Up Adoption Strategy : Monday.com excels at land-and-expand through individual teams, with employee champions driving wider adoption throughout organizations.

SMB 279
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The Complete Guide to SaaS Pricing Strategy

Tom Tunguz

But throughout this turmoil, startups must adopt a process to craft a good pricing strategy, and re-evaluate prices periodically, at least once per year. The Three Core Pricing Strategies There are only three pricing strategies startups should pursue: Maximization, Penetration and Skimming.

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The Top 10 Strategies Toast’s CRO Uses to Crush Quotas

SaaStr

Top 10 Strategies Toasts CRO Uses to Crush Sales Quotas So a little while ago Toasts CRO Jonathan Vassil joined Sam Blond on SaaStr CRO Confidential on how Toast built one of the strongest but toughest rocketship in sales: a lower gross margin, lower ACV ($10k), sales-led SMB sales motion. Even with SMB Sales.

Strategy 144
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Scaling 6 Products to $100M+ ARR Each: Samsara’s CPO Kiren Sekar on Multi-Product Growth

SaaStr

Kiren Sekar, Chief Strategy Officer and founding team member at Samsara, came to SaaStr Annual to do one of our best deep dives even on going multi-product. Mid-Market Is The Perfect Laboratory For Both Product and Go-To-Market Development Most founders falsely view market segmentation as a binary choice between SMB and Enterprise.

Scale 263
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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.

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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. Deal Strategy : AIs will independently analyze deal progression, suggest next steps, and even flag at-risk opportunities before humans notice the warning signs. But you can automate 30%-40% of support for real … with top 10% CSAT. So what does that mean for inside sales?

Scale 248
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How SMB Digital Brands Can Win the Best Talent

FastSpring

In this episode of Growth Stage, we interview Lizzie Mintus Founder and CEO of Here’s Waldo Recruiting and host of The Heres Waldo Podcast about her thoughts on: The most effective recruiting strategies for SMBs. It’s so difficult for SMBs to compete for the best talent. Insights on why the best candidates say YES!

SMB 108