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SaaS Is Still Slowing Down, Unfortunately: What Q1 2025 Numbers Reveal About the Cloud Software Market

SaaStr

Instead, we’re seeing a market characterized by extreme boom-bust cycles that make planning and forecasting incredibly challenging. Several macro factors are converging to create this perfect storm: Enterprise Budget Scrutiny : CFOs are demanding higher ROI thresholds for software investments. What’s Driving the Decline?

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How to Train Your Sales Leaders: Key Learnings from HubSpot and BILL with Michelle Benfer

SaaStr

Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth. “At HubSpot, I had over 100 frontline sales managers reporting to me. Percentage of reps at different attainment levels (>100%, 90-100%, etc.)

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SaaStr AI App of the Week: Syllable.ai

SaaStr

Real-Time Data & Weather Services Get real-time weather updates and forecasts through an AI agent connected to live weather data from OpenMeteo. The Investment Story Syllable has raised $103M total funding, including a $40M Series C led by TCV, with backing from Oak HC/FT, Section32, and Verily. Who Should Evaluate Syllable.ai

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Top 10 Unexpected Learnings from Scaling Wiz From $0 to The First $100M ARR with founding CRO Colin Jones and Sam Blond

SaaStr

Radical Transparency in Growth Planning While most revenue leaders deliberately “sandbag” forecasts to ensure they can over-deliver, Colin Jones did the exact opposite at Wiz. This approach required immense trust from the CEO to invest millions ahead of proven results. He now serves as President of Sublime Security.

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GTM in The Age of AI: The Top 10 Learnings from ICONIQ’s 2025 B2B SaaS Report

SaaStr

It’s about fundamental organizational redesign —from pricing models (hybrid consumption/subscription) to team structures (forward-deployed engineers vs traditional CSMs) to investment priorities (94% AI spend increases among high-growth companies). The message is clear: The Age of AI isn’t coming—it’s here.

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The Early Days: How Deel Went From $1m to $100m ARR in Just 20 Months

SaaStr

Forecast Everything, But Plan for Chaos “It’s really hard to forecast when the timing is really good and everything could change. Forecast is not only about headcount planning but also revenue numbers—to hit the revenue numbers, what kind of resources do we need?

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

SaaStr

Investing for growth has been pretty flat year over year for SMBs, which means there is money there, but they’re holding onto it. They’re asking for moving money faster, creating a specific workflow, and insights and forecasting so they can be strategic about what they’re spending. So I call this the wait-and-see economy.”

SMB