Remove Payment Features Remove Scale Remove Trends
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Usage-Based Revenue Models: Successes and Pitfalls from Checkr COO Lindsey Scrase on CRO Confidential

SaaStr

When Lindsey joined, she inherited an already built-out self-serve/PLG model for small businesses and a mid-market and enterprise sales, customer success, and post-sales team. But at the start of its expansion play, Checkr’s enterprise motion failed, and sales cycles were slow, taking up to a year for $100k & up deals.

Revenue 293
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Is AI Penetration … Slowing Down? Ramp Says Possibly

SaaStr

New spending data from Ramp reveals a possible trend: end user AI adoption may be hitting its first growth slow down. Moving from AI pilots to production-grade implementations requires solving hard technical problems around data pipelines, security, compliance, and workflow integration.

AI 233
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Clouded Judgement - 3.28.25 - The New AI Risk Curve

Clouded Judgement

Every week I’ll provide updates on the latest trends in cloud software companies. Starting and scaling a software company was really hard. Starting and scaling a software company was really hard. If you wanted to scale users and growth, you needed to scale a physical data infrastructure footprint.

Cloud 302
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Unlocking Growth in the Internet Economy: a Perspective from Stripe Head of Invoicing, Suzanne Xie (Video)

SaaStr

These days, as the business lead for invoicing at Stripe, Xie has earned her own stripes in navigating the unique challenges of building and thriving in the SaaS marketplace. Maybe your billing system is not ready, your invoicing is a patchwork, or your reconciliation and invoicing have to be done manually.

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The 3 Secret Ingredients for Scaling to $100M ARR with Bitly CEO and CPO

SaaStr

Bitly CEO Toby Gabriner and CPO Kelsey Stevenson share the three secret ingredients that helped them when scaling to $100M ARR and what they could have done differently. Kelsey joined them as CPO, and they started experimenting with less expensive packages downmarket where customers could go online and set up a subscription.

Scale 300
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How to Choose a Payment Solution That Scales with You

Stax

As your business grows, the tools powering it need to evolve tooand that includes your payment solution. While many platforms are built for getting started, not all are designed to support scale. Volume caps, poor integrations, manual reconciliation, and clunky mobile checkout are all signs your current system wont scale with you.

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

Stax

Fee structures matter; understand the differences between interchange plus, flat rate, tiered, and subscription pricing to find the most transparent and cost-effective option. Talk to sales What Are Credit Card Merchant Services? Together, these tools form the foundation of your ability to process payments reliably and securely.