SaaStr

JUNE 6, 2025

Several macro factors are converging to create this perfect storm: Enterprise Budget Scrutiny : CFOs are demanding higher ROI thresholds for software investments. The low-hanging fruit of digital transformation has been picked, and companies are being more selective about additional software investments. Slower New Customer Growth.

Cloud 251

Cloud Software Marketing SaaS 251

SaaStr

JULY 11, 2025

Financial Services: Mortgage & Loan Processing Help users explore mortgage options by collecting key inputs like purchase price, credit score, down payment, and property location, then presenting tailored loan choices with current rates. Pay only for what you use with transparent pass-through pricing for 3rd party integrations.

Payment Solutions 267

Payment Solutions Scale AI Payment Services 267

SaaStr

MAY 20, 2025

Pricing Model Evolution : HubSpot’s multi-tiered pricing approachfrom free tools to enterprise solutionscreates natural upgrade paths as companies grow, maximizing lifetime value while maintaining strong operating margins (14% non-GAAP operating margin in Q1 2025). Their ecosystem extends their reach globally.

SMB 273

SMB Scale Education AI 273

SaaStr

APRIL 1, 2023

So everyone is now paying the price for lowering the bar in the Boom Times of mid ‘20 to early ‘22. And now we’re paying the price. The same things happened in VC and investing. I did some of this myself, both on people and investments. Better to do with fewer people, fewer investments, fewer initiatives.

Sales Hiring 312

Sales Hiring Investment Leadership Startup 312

SaaStr

APRIL 19, 2025

Dear SaaStr: Should I Buy a Great “ com” At a Crazy Price or Just Stick What the “ ai” We Already Have? One of the top SaaStr Fund investments is Owner, growing incredibly quickly. domain is confusing customers or holding back your brand, it might be worth the investment. But if youre finding that the.ai

AI 169

AI Pricing Banking Branding 169

SaaStr

NOVEMBER 13, 2024

But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. But SMBs in the middle have become more cost and price-sensitive. #10. Outside of a pre-IPO phase, Klaviyo has been cash-flow positive or close for most of its history. Just not as quickly as overall revenue growth. #4.

Scale 301

Scale SMB Scaling Enterprise 301

SaaStr

MAY 23, 2025

When SaaStr Fund made the first investment in RevenueCat back in 2018, nobody could have predicted that this “simple API for managing in-app subscriptions” would become the infrastructure powering 33% of all mobile subscription apps and reach a $500M valuation in 2025. The SaaStr Fund Thesis: Mobile Subscriptions Will Explode.

Payments 279

Payments Payment Solutions Underperforming Technical Team Payment Methods 279

SaaStr

JUNE 20, 2025

This isn’t just about productivity — it’s about economic disruption : The Agent Economics: Traditional SaaS: $3,500 per employee annually across organizations AI Agents: Can replace entire job functions for <$100/month The math may be devastating for high priced seat-based pricing models 3. Palantir was ready.

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

SaaStr

OCTOBER 30, 2024

We’re obviously written up a lot about Fundraising and Investing here on SaaStr.com, but time and time again, SaaStr CEO and Founder Jason Lemkin has seen so many Founders sign a bad term sheet based on gut instinct, VC celebrity or vibes, and while that may be fine, it’s not enough.

Venture Capital 312

Venture Capital Software Review Investment Startup 312

SaaStr

NOVEMBER 2, 2024

Having been through 4 acquisitions in different forms (founder, exec, etc), it’s a lot like a venture capital investment. A ton of time is invested negotiating price, and then way, way too much time on inconsequential legal terms, and then … it closes. Not really.

Venture Capital 261

Venture Capital Acquisition Investment Technology 261

SaaStr

JULY 6, 2025

This extreme revenue concentration shows Figma’s ability to create significant value for mid-market and enterprise customers—a small number of deeply engaged accounts drive the majority of revenue, indicating strong product-market fit at scale and pricing power within larger organizations.

Software Review 264

Software Review Scale Systems Review Enterprise 264

SaaStr

NOVEMBER 17, 2024

3 Came from the Investment Bank They Hired. In my experience, hiring an investment bank to help you in any acquisition > $100m or so is critical. But Andy got 3 other firm offers through the bank he hired — along with a price more than $10m higher. They Ran a Crisp, Tight Process And Got 4 Offers to Buy Them.

Sales Hiring 293

Sales Hiring Banking Sales SaaS 293

Sales Hacker

FEBRUARY 7, 2025

SaaS pricing isn’t static – it’s a living strategy that grows with your company. In this article we dive into a playbook for pricing across different stages of company growth, inspired by Geoffrey Moore’s Crossing the Chasm. Tiered pricing models emerge to address these differences.

Pricing 108

Pricing Scale SaaS Technical Review 108

Tom Tunguz

DECEMBER 26, 2022

A former venture capitalist, Mark Leonard started Constellation in 1995 with $15m of outside investment & a goal of buying vertical software companies with a moat & good unit economics. Price Increases. New bookings added 10% ; price increases 5%. Growth Source. Acquisition. New Bookings. Contraction. -3%. Net Growth.

Software Review 295

Software Review Investment Software Acquisition 295

Tom Tunguz

AUGUST 7, 2022

But no relationship exists between the Nasdaq’s price level & multiples. The data suggests the market has attained a pricing floor. I can’t ascertain how record fundraising inflows into private equity funds might bolster these prices, but the billions burning holes in PE wallets must impel some activity.

Acquisition 324

Acquisition Pricing Startup Software 324

SaaStr

JULY 5, 2025

I get to set the price of the apples because they’re my apples. Price Determines Product Quality (Self-Fulfilling Prophecy) “When you’re making a product, the price you set will determine how good your product is. net income, 111.5% revenue growth year-over-year 2013 IPO : $129.5M net income, 111.5%

Underperforming Technical Team 231

Underperforming Technical Team Sales Hiring compliance Pricing 231

Clouded Judgement

JUNE 17, 2025

This matters a lot more when stock prices are going down, and management teams often grant additional shares to make employees whole (thus increasing dilution even more) Net Revenue Retention High net revenue retention is the fourth aspect of a successful quarter, and one of my favorite metrics to evaluate in private SaaS companies.

Cloud 277

Cloud Software Benchmarks Retention 277

SaaStr

DECEMBER 17, 2024

And as stock prices rip higher, growth VC floods back in. But overall, the growth investments weren’t big wins. 2021 prices were certainly inflated in many cases from valuations today. So SaaS is back. Top SaaS stocks are on fire the past few months, and the SaaS downturn in B2B2B appears to be behind us. At least at IPO.

SaaS 261

SaaS AI Pricing Metrics 261

SaaStr

JUNE 11, 2025

The B2B / SaaS Parallel : Many SaaS companies build their entire business on one pricing model, one customer segment, or one distribution channel. This early investment in regulatory compliance has become their key differentiator against Tether and newer entrants. Circle trading at $85 up from $31 IPO price.

compliance 241

compliance Marketplace as a Service B2B Healthcare 241

SaaStr

NOVEMBER 28, 2024

I try to look at two things in Vertical SaaS startups, at least when investing : Will everyone in the vertical / industry use it? The good news is, you can support these price points effectively with a very efficient inbound sales team, and/or a mix of self-serve and sales-led. At two different price points. That’s the question.

Payment Solutions 261

Payment Solutions Inbound Sales Team Marketing Scale 261

Sales Hacker

NOVEMBER 29, 2024

GTMfund’s 3 Areas of Focus for Investing Thanksgiving weekend is always a period of reflection and gratitude. Reflection across go-to-market trends, but also on the investment front (not to mention community !). A common misconception is that the name is representative of the type of software we invest in.

Investment 110

Investment Technical Review Development Team Review Scale 110

SaaStr

DECEMBER 26, 2024

I havent done that, but Ive done handshake deals in one day in maybe 50% of my investments (i.e, Not literally months to do the homework that doesnt take long but sometimes months to see enough progress for the investment to make sense to me, to connect enough dots. Yes, term sheets get done in one day.

Investment 246

Investment Pricing Leadership 246

SaaStr

MARCH 22, 2024

Dear SaaStr: How Can I Convince My Investor We’ll Double Their Investment By The Next Round? If you are a VC / private investor, there’s a key meta question: why invest now ? Because, at the same price … later is always better. This is really the reason most very early-stage investments get done.

Investment 283

Investment Pricing 283

SaaStr

JUNE 7, 2025

The shift from “innovation budget” to “operational budget” means AI tools must compete directly with established software investments—and many aren’t winning those comparisons yet. The Hidden Enterprise Pipeline Card spend data, while valuable, captures only a portion of enterprise AI investment.

AI 281

AI Payment Services Payments Scale 281

SaaStr

JUNE 23, 2025

It’s the emergence of a new category that’s attracting billions in investment and fundamentally disrupting the $500B+ software development market. If model providers change pricing or restrict access, margins could compress quickly. Usage-based pricing aligns costs with value creation and enables explosive growth.

Software Review 212

Software Review AI Technical Review Venture Capital 212

SaaStr

MARCH 24, 2025

And while the Wiz deal hasn’t closed yet, seeing a record M&A deal price fuels more VC investment. I asked founder Ryan Smith at SaaStr Annual what he thought of that record price? In part, because they see the absolute potential exit sizes just going up and up. “The next one will be even higher.

Acquisition 233

Acquisition Cloud Pricing Investment 233

SaaStr

JULY 7, 2025

👑 Larry’s Long-Term Vision : CEO Larry Ellison’s early AI investments and partnerships (particularly around autonomous database technology) positioned Oracle perfectly for the AI infrastructure boom. 💾 Data as the Moat : While others chased AI features, Oracle doubled down on what it does best—managing enterprise data at scale.

AI 204

AI Cybersecurity Artificial Intelligence SaaS 204

SaaStr

JUNE 24, 2025

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). This isn’t about sprinkling ChatGPT into your sales process.

Scale 188

Scale AI B2B SaaS 188

SaaStr

NOVEMBER 7, 2024

Models built by OpenAI, Google, and Anthropic have billions of dollars to invest in training these models, so you have more powerful engines under the hood at no cost to you. The price for inference has massively plummeted this year, so you have more powerful models to build into your application, and they cost less every time you use them.

AI 261

AI Artificial Intelligence ChatGPT Mobile 261

SaaStr

MARCH 8, 2024

With everything in AI moving so rapidly, what’s the best way to price Artificial Intelligence products or SaaS tools with custom AI features and integrations? So we asked the expert, Sandhya Hegde, General Partner at Unusual Ventures to share her best practices and trends for pricing and packaging AI products. Why is pricing so tricky?

AI 268

AI Pricing Artificial Intelligence SaaS 268

SaaStr

DECEMBER 25, 2023

G2 had us back for another great deep dive on just where SaaS investing is there days, and it was a great panel: Accel Partner Arun Mathew Inspired Capital Founder & Managing Partner Alexa von Tobel Salesforce Ventures Managing Partner Paul Drews and Jason Lemkin! Low investment multiples pose a key challenge.

B2B 282

B2B Investment Venture Capital SaaS 282

Clouded Judgement

NOVEMBER 18, 2024

The purpose of the detailed information is to help investors (both institutional and retail) make informed investment decisions. As far as an expected timeline - typically companies launch their roadshow ~2-3 weeks after filing their initial S-1 (the roadshow launches with an updated S-1 that contains a price range).

Benchmarks 299

Benchmarks Payments Payment Services SaaS Payments 299

SaaStr

JANUARY 25, 2025

Founded 2008 * Raises ~$53m in VC * Sells 17 years later for $53m * Only $20m of that cash * 2x ARR price * 1x What Raised Just plain tough. Thats just how investing work. I used to sort of think that way. But the reality is, VCs only make real money if founders make a ton of money. The stakes go way up. So who makes what here?

Venture Capital 239

Venture Capital Investment Retention Pricing 239

SaaStr

JULY 11, 2025

Competition and Differentiation: Founders worry about competitors copying their product or undercutting them on price. Investing in customer success early can make a huge difference here. But not most of us. It’s often the only way to scale meaningfully in SaaS. And you should. The pace here has accelerated even more with AI.

Scale 227

Scale Part-Time VPE Scaling Sales Hiring 227

SaaStr

DECEMBER 27, 2024

Engineering resources: With thousands of engineers, companies like HubSpot can make substantial AI investments when they choose to 3. The Future of AI in Customer Support While many vendors are achieving similar baseline results with AI customer support, Brian believes we’re still early in unlocking its full potential.

AI 284

AI Marketing SaaS Interviewing 284

SaaStr

JULY 1, 2025

The key is concentrated investment in differentiation, not diversification. Adobe deal (2022): $20B fixed price IPO potential (2025): $18-27B range + $1B breakup fee received Net outcome: +$4-8B value creation vs. ” Companies achieving 60%+ Rule of 40 scores trade at 2-3x premium multiples.

B2B 169

B2B Benchmarks Retention Enterprise 169

SaaStr

NOVEMBER 19, 2024

Walker Research found in 2024 that the customer experience is now equal to price and product regarding key brand differentiators. Organizations that invest heavily in customer success earlier see much higher customer retention and loyalty than the competition. For example, say your company is going upmarket to Enterprise.

Customer Success 284

Customer Success Scaling Social Media Enterprise readiness 284