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10 Things That Are Different in Vertical SMB Sales with Toast’s CRO

SaaStr

Jonathan Vassel, CRO at Toast helped scale the company from $20M ARR in 2017 to $1.7B+ ARR in Q1 2025 and a stunning $25B market cap. Toast’s CRO Jonathan Vassel shared fascinating insights on how vertical SMB sales is fundamentally different—and why those differences can become massive competitive advantages.

SMB
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The Complete Guide to SaaS Pricing Strategy

Tom Tunguz

The very best companies lead their customers in that dance. Many mid-market software companies price with the goal of revenue maximization, negotiating for the highest possible price in each sale. Penetration pricing leads to land-and-expand sales tactics. Most startups play defense when discussing pricing with customers.

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The Rise of Vertical SaaS: Achieving 110% NRR from SMBs with Mangomint’s CEO

SaaStr

For restaurants, it’s the back end, front end, point of sale, payroll, ERP, and workforce management. Mangomint has one onboarding manager for every two sales reps, but with no contracts and a 30-day free trial, onboarding starts during the trial. Most sales reps hate it. There will likely be multiple Toasts for SMBs.

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Credit Card Merchant Services: What to Look for (and What Most Businesses Miss)

Stax

Talk to sales What Are Credit Card Merchant Services? These services enable you to process credit card payments online, in person, and on the go, and include everything from secure payment gateways to merchant accounts and point of sale (POS) systems.

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Webinar Recap | Scaling Payments: Strategies to Attach and Amplify Processing Volume

Stax

Our host, Ray Lau , VP of Marketing, led an insightful discussion with Jeremy Krahl , SVP of Payment Partner Growth; Fred Nelson , VP of Sales Enablement; and Brandon Ewell , Partner Growth Manager. Brandon Ewell added that the ideal sales approach depends heavily on where your organization is in their payments journey.

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Integrated payments: Definition, types, and examples

Payrix

The setup connects payment processing with a point-of-sale (POS) system software that can sync with other business-critical systems and streamline processes. Often, software customers have to hop from system to system and spend time reconciling their payments against their sales. Learn more about Embedded Finance.

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Software-led payments: What’s on the horizon for platforms in 2025? | Episode 46

Payrix

As a pioneer in driving security and payments for SaaS companies, he has served in several executive leadership roles across his diverse payments, software, and platforms background, leading high-performing teams and businesses to exponential growth. Matt Downs Yeah, I think scale matters, to be self-promoting, I don’t mind doing that.