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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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How to Structure Your Sales Compensation Plan to Deliberately Undersell

Tom Tunguz

In Deliberately Underselling as Sales Strategy , I wrote about the importance of sizing contracts below customer needs to ensure customer success. “A key part of the formula: crafting the right account executive compensation structure to reward this strategy.”

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Usage-Based Revenue Models: Successes and Pitfalls from Checkr COO Lindsey Scrase on CRO Confidential

SaaStr

Checkr’s go-to-market strategy was already well-established when Lindsay joined in 2022. By restructuring compensation plans to focus more on actual revenue realization, Lindsey was able to better align seller behavior with company objectives.

Revenue 293
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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. 5 Interesting Learnings from Toast at $1.1

Strategy 137
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Deliberately Underselling as Sales Strategy

Tom Tunguz

But, as Lee Kirkpatrick, former Twilio CFO, shared during Office Hours , Twilio employed this strategy to achieve top quartile NDR while achieving strong ARR predictability with a usage-based pricing model. A key part of the formula: crafting the right account executive compensation structure to reward this strategy.

Strategy 356
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The 2026 Sales Team: 50% Humans, 50% AIs. All 1 Team.

SaaStr

Deal Strategy : AIs will independently analyze deal progression, suggest next steps, and even flag at-risk opportunities before humans notice the warning signs. Addressing the Compensation Question How do you compensate a team that’s half human, half AI? We’re already here.

Scale 221
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How to Transition From Founder-Led Sales to Your First Sales Team: 9 Top Tips

SaaStr

Compensate Relatively Generously. Use the early months to refine your process, adjust compensation plans, and learn what works. Your insights will help refine the strategy and keep the team aligned with your vision. You can hire folks from all different backgrounds to work for you directly in sales. And Reps Have to Eat.

Scale 181