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PE Loves SaaS Again: Thoma Bravo Buys Olo for $2 Billion

SaaStr

Quick Stats: Founded: 2005 (20-year-old company) 2024 Revenue: $285M (up 25% YoY from $228M in 2023) Q1 2025 Revenue: $80.7M (up 21% YoY), $323M annualized run rate Profitability: $1.8M That’s $10.25 share, 65% premium) Why This Deal Matters for B2B and SaaS This isn’t just another PE rollup. But the pruning worked.

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

SaaStr

If we step back to 2004-2005, when BILL was just an idea, the first realization was that this had to be simple. That’s the part that becomes a moat competitively. BILL is moving money and doing it well, all while being highly regulated. Bill Has Acheived 80% Gross Margins — How?

SMB 307
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AI Apps The SaaStr Team Loves — and Uses Every Day

SaaStr

Hours in Google Slides, struggling with charts that looked like they were designed in 2005, and presentations that somehow managed to make our impressive data look boring. Gamma: Sponsor Collateral That Actually Impresses Creating sponsor materials used to be a nightmare. We often needed our designer to help with templates.

AI 250
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Navan Files for IPO: The Opening of B2B IPO Floodgates?

SaaStr

Considering options Klarna 2005 Sebastian Siemiatkowski Fintech $2B $6.7B Revenue Valuation IPO Timeline Databricks 2013 Ali Ghodsi Data Analytics $2.4B $62B 2025-2026 Netskope 2012 Sanjay Beri Cybersecurity $487M $7.5B Q3-Q4 2025 Discord 2015 Humam Sakhnini* Communication ~$600M $15B 2025 Figma 2012 Dylan Field Design Software $600M $12.5B

B2B 187
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The Best FinTechs for PayFac-as-a-Service: Because DIY is Overrated

USIO

Biggest Challenge: Feels like using 2005-era technology. But if youre looking for a modern, developer-friendly PayFac solution, this probably isnt it. Biggest Perk: Global payments, traditional acquiring. Customer Support Rating: 5/10 Theyll answer, but expect a lot of paperwork.

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GTM 126: Reverse Engineering the Founder Journey: From Scaling Twitter Ads to $650M, 20 Years Operating, and a Webflow Acquisition | Guy Yalif

Sales Hacker

Scott Barker: [15:22] Yeah um absolutely so then Then, I guess, the next step from there, so then in 2005, you make the jump to Yahoo. Is Yahoo where, it sounds like that’s where the gears started cranking for what would become Intellimize? I think you also met your co-founder there.

Scale 101
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The AI messaging pivot happening across SaaS

Sales Hacker

Describing your product as AI-powered is like saying its internet-connected in 2005. As this flood of AI messaging hit, a lot of people quickly became numb to it. Now in 2025, AI promises have simply become baseline expectations. Its expected, not a value add. Companies are testing, and the results are showing.