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The Great IPO Awakening: Are We Back?

By Jason Lemkin
Monday, September 15, 2025 | Exit Strategy, Fundraising, Scale

Last week marked the busiest IPO stretch since 2021. Six companies raised $4.4 billion in five days. But is this the sustainable comeback founders and VCs have been waiting for, or just another false dawn?

The IPO window isn’t just cracking open, it’s swinging wide. Smart companies with strong fundamentals should move now, while conservative pricing and investor selectivity create the perfect storm for sustainable public market success.

Last Week, We Almost Got Back to The IPO Pace of 2021.

Last week delivered something we haven’t seen since November 2021: six companies raising over $100 million each in a single week. The $4.4 billion total represented the most concentrated IPO activity in nearly four years, pushing 2025’s total traditional IPO proceeds to $25 billion—the highest since the 2021 peak.

Here’s what made it historic:

Seven sizable IPOs debuted (including SPACs), the most in nearly four years
Five of six major deals priced above their marketed ranges
25x oversubscription on marquee names like Klarna and Figure
Back-to-back active weeks expected for the first time since December 2021

But unlike 2021’s frothy valuations and subsequent crashes, this wave is built on more fundamentals, somewhat conservative pricing, and genuine investor selectivity.

THE GREAT IPO AWAKENING

Join SaaStr AI Day Live on October 8

SaaStr AI Day is BACK!

Join the leaders who are shaping the future of AI in SaaS:

Jason Lemkin - CEO & Founder, SaaStr, and Amelia Lerutte - Chief AI Officer, SaaStr
Denise Persson - CMO, Snowflake, and Chris Degnan - Founding CRO & Board Member, Snowflake
David Boskovic - CEO & Founder, Flatfile
Santiago Suarez Ordoñez - Co-Founder & CEO, Momentum
Marty Ringlein - Co-Founder & CEO, Agree.com
Darlene Volas - Head of Global Field Engineering, Firebolt
Anis Bennaceur - Co-Founder & CEO, Attention

Get insider insights on AI strategies, implementation secrets, and what's next for B2B companies leveraging artificial intelligence.

It's all happening live on October 8, 2025

Don't miss out on the conversations that will define the next era of SaaS.

FREE AI DAY

What’s Better, Selling for $50m Today or $1B Later? It Can Be Murky

By Jason Lemkin
Monday, September 14, 2025 | Blog Posts

The AI Agent Reality Check: Why Managing Always-On AI Workers Is Your Next Big Challenge

Why That “$50M to $1B” Acquisition Offer Isn’t Always What It Seems: A Founder Reality Check

I’ve seen this story play out multiple times as an investor, and the lessons are both counterintuitive and crucial.

TL;DR: In one of my very first investments, the founders turned down a $50M acquisition to see their start-up sell for $1B years later – yet walked away with roughly the same personal outcome they would have had by taking the first deal.

The Tempting Early Offer.

Way back in 2013, I made an early investment in a promising startup. The team had built impressive traction without raising much capital – maintaining strong ownership and control. It was early, but by $1m ARR they’d pulled ahead of their seemingly similar legion of competitors.

Then came the moment many founders dream of: the CEO of a public company wanted to acquire them for $50 million. The founder actually reached out to me to have lunch, and asked if the founders would. be receptive. I said I thought so, but I didn’t know.

With minimal outside capital raised, this would have been life-changing money for the founding team. But they had bigger visions. They said no. In fact — they said “No at Any Price.”

The Long, Long Road to a Bigger Exit.

8 years later they were acquired for $1 Billion. What followed was the entrepreneurial equivalent of climbing startup Everst:

5 different management teams
2 more CEOs
4 more venture capital rounds
Years of grinding, pivoting, and scaling
Significant dilution with each new funding round

Eventually, the company sold for nearly $1 billion – a 20x multiple on that original offer!

WHAT'S BETTER?

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The Silent, Lurking Churn: Activation Rates Less Than 90%

By Jason Lemkin
Monday, September 15, 2025 | Customer Success

It took me a little while to see activation rates as literally one of the 3-4 most important metrics in SaaS, but it probably is.

I started to track activation rates at a lot of start-ups I work with, and I saw numbers that shocked me. I often see 60% or so activation rates 30 days in.

Think about that. That means after all the time and money put into building your product, marketing your product, trialing your product, demo’ing your product, selling your product, closing the deal, celebrating … and then … a ton of those customers are immediately at risk. Why? They don’t deploy.

I don’t have a perfect metric, but after working on this with a dozen + SaaS companies recently, I have a simple heuristic:

90% or more of your customers need to activate in the shortest practical time. And you need to track this, measure it, and discuss it weekly. Every week.

Time to Value (TTV) is a common way to measure true activation rates:

SMB SaaS: For smaller businesses, TTV should ideally be under 30 days, and often much faster. Companies like Klaviyo, for example, hit 90% activation within 30 days, even with 100,000+ SMB customers and $600M in ARR. If you’re selling to SMBs, speed is critical—if they don’t see value quickly, they’ll churn fast.
Mid-Market SaaS: For mid-sized companies, TTV often stretches to 30-90 days. These customers may require more customization, training, or integrations, but they still expect to see ROI within the first quarter.
Enterprise SaaS: For large enterprises, TTV can take 3-6 months or more, especially if there’s a significant implementation phase. However, even in enterprise sales, you should aim to show some value—like a working pilot or initial results—within the first 90 days.

YOU NEED AN 90% ACTIVATION RATE

The AI Marketing Revolution: Key Insights from G2’s CMO on How B2B Buying Has Forever Changed

By Jason Lemkin
Saturday, September 13, 2025 | Marketing

From the new SaaStr “Swapping Notes” podcast series – essential listening for every B2B founder and marketing leader navigating the AI transformation

Speaker Bios

Sydney Sloan, CMO at G2

Sydney Sloan brings over a decade of B2B marketing excellence to her role as Chief Marketing Officer at G2, the world’s largest software marketplace. Previously, she led marketing initiatives at high-growth companies including SalesLoft and Adobe, where she honed her expertise in scaling go-to-market strategies. Beyond her operating role, Sydney is an active LP at Stage 2 Capital and part of the Scale Ventures network, where she advises founders on growth strategies. Her unique position at G2 gives her unparalleled visibility into both sides of the B2B buying equation – how buyers research and how sellers adapt.

Guillaume Cabane, Co-Founder and General Partner at HyperGrowth Partners

Guillaume Cabane is Co-Founder and General Partner at HyperGrowth Partners, where he advises approximately 20 of the best B2B companies annually on accelerating growth. His impressive operating background includes building growth teams at segment-defining companies like Segment, Drift, and Gorgeous, followed by leading all of marketing at Ramp, the fast-growing fintech company. With over 10 years of hands-on B2B marketing experience, Guillaume has developed a reputation for identifying and implementing growth strategies that work at scale.

Amelia Lerutte, Chief AI Officer at SaaStr

Amelia Lerutte serves as Chief AI Officer at SaaStr, where she leads the organization’s AI strategy and implementation across all verticals. She hosts the “Swapping Notes” podcast series, focusing on practical AI applications in B2B software. Her role puts her at the center of the AI transformation happening across the SaaS ecosystem, working directly with founders and operators implementing AI strategies.

THE AI MARKETING REVOLUTION

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Is SEO Dead? Maybe, But Not At SaaStr. Our Search Impressions Are Up a Stunning 5x in Last 12 Months!

By Jason Lemkin
Saturday, September 13, 2025 | Artificial Intelligence (AI), SaaStr.Ai

Is SEO Dead? Maybe, But Not At SaaStr. Our Search Impressions Are Up a Stunning 5x in Last 12 Months!

A transparent look at what’s really working in B2B content marketing in 2025.

Bottom Line: While everyone’s declaring SEO dead and pivoting to AI-generated content farms, we took the opposite approach. The result? 33.6M search impressions annually, 5x growth in 12 months, and complete category dominance in B2B SaaS search.

The “SEO is Dead” Narrative is Wrong (At Least for Us).

You’ve heard it everywhere: Google favors AI slop, authentic content doesn’t rank, and SEO is a waste of time in 2025.

Our data tells a different story.

Over the past 12 months, SaaStr’s organic search performance has exploded:

From 50K to 245K daily impressions (that’s 5x growth)
33.6M total impressions in the last year
327K clicks from organic search
1% average click-through rate (double the industry standard)

While other B2B publications are chasing ChatGPT SEO hacks and pumping out generic listicles, we doubled down on what we’ve always done: deep, authentic, data-driven content about real SaaS companies and real growth challenges.

SAASTR'S IMPRESSIONS ARE UP 5X!

Dear SaaStr: What Are The Top Red Flags for VCs When Deciding to Invest in a Startup?

By Jason Lemkin
Saturday, September 13, 2025 | Q&A

When VCs evaluate startups, there are definitely some red flags that can make them hesitate—or outright pass—on an investment.

Here are the key factors that are often considered “bad” news:

1. Weak Founder or Team

VCs invest in people as much as they invest in ideas. If the founder lacks vision, resilience, or the ability to execute, that’s a dealbreaker. A founder who can’t clearly articulate their strategy or who seems uncoachable will raise concerns. Early-stage VCs, in particular, are betting on the founder more than anything else.

2. Small or Unclear Market

If the total addressable market (TAM) is too small, or if the startup can’t clearly define its market, VCs will struggle to see how the company can scale. A small market means limited upside, and VCs need big outcomes to make their portfolio math work. Remember, they’re looking for companies that can deliver 100x or more returns for early stage, and 10x or more returns for late stage investments.

3. High Churn or Poor Retention

For B2B startups especially, churn is a killer. If customers aren’t sticking around, it’s a sign that the product isn’t delivering enough value. VCs know that poor retention makes it nearly impossible to scale efficiently. A startup with high churn is a risky bet.

4. Overly Aggressive Burn Rate

If a startup is burning cash too quickly without clear ROI, it’s a red flag. VCs want to see that founders are capital-efficient and can stretch their runway. A high burn rate without corresponding growth signals poor financial discipline and increases the risk of running out of cash before hitting key milestones.

5. No Clear Differentiation

If the startup doesn’t have a unique value proposition or defensible moat, it’s hard to justify an investment. VCs need to see how the company will stand out in a crowded market and fend off competitors. Without differentiation, the startup risks becoming a “me too” product.

THE TOP RED FLAGS FOR VCS

10 Hard-Won Lessons from Jeff Lawson (Founding CEO Twilio) on AI Disruption, Big M&A, and the Future of SaaS

By Jason Lemkin
Sunday, September 14, 2025 | Blog Posts

This week one of our favorite founders at SaaStr, Jeff Lawson founding CEO of $15B+ Twilio, joined the 20VC x SaaStr pod live with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll.

Jeff Lawson built Twilio from zero to IPO and beyond, navigating the complexities of developer APIs, public company M&A, and ultimately stepping down as CEO. His insights from the trenches offer invaluable lessons for founders building at scale.

10 HARD-WON LESSONS

Dear SaaStr: What Are the Slides That Should Be in Every VC Pitch Deck?

By Jason Lemkin
Sunday, September 14, 2025 | Q&A

Here’s the structure I like to see in a pitch deck—it’s simple, clear, and designed to get investors excited without wasting time. Every slide should have a purpose, and the first few are critical to hook the audience:

1. Title Slide

Keep it clean—company name, tagline, and maybe a killer stat or tagline that grabs attention. For example, “The #1 AI Platform for Customer Success.”

2. Problem

What’s the pain point? Be specific and data-driven. Show why this problem is urgent and worth solving.

3. Solution

How are you solving it? Keep it concise and compelling. A visual or demo screenshot can help here.

4. Why Now?

Timing is everything. Show why this is the perfect moment for your solution to succeed. For example, “AI adoption in customer success is growing 40% YoY.”

5. Market Opportunity (TAM/SAM/SOM)

Break down your TAM, SAM, and SOM with clear math. Tie it directly to your pricing model and ICP. Investors want to see how big this can get and how realistic your assumptions are [8].

6. Product

Show the product in action. Use screenshots, mockups, or a short demo video. Highlight what makes it unique.

7. Traction

If you have revenue, customers, or growth metrics, this is where you shine. Be specific—“$1M ARR, growing 20% MoM” is far more compelling than vague claims.

8. Business Model

How do you make money? Show your pricing, ACV, and any early signs of strong unit economics (e.g., CAC, LTV).

9. Go-to-Market Strategy

How are you acquiring customers? Highlight your sales motion (PLG, enterprise sales, etc.) and any early wins.

10. Competition

Acknowledge your competitors and show how you’re different. Be honest and self-aware—it makes you look smarter. Include the top 8-10 competitors and position yourself clearly.

11. Team

Why are you the team to win? Highlight relevant experience and any key hires you’ve made or plan to make.

12. Financials

Keep it high-level—current revenue, burn rate, and projections for the next 12-24 months. Don’t overcomplicate it.

13. The Ask

Be direct. How much are you raising, and what will you achieve with it? For example, “We’re raising $3M to scale from $1M to $5M ARR in 18 months.”

14. **Closing Slide**

End with your logo, tagline, and contact info. Make it easy for investors to follow up.

Key Tips:

– **First Slide Sells the Deal**: Your first slide should be so good that it could sell the whole company on its own.

– **Keep It Fairly Short — But Complete**: 15-20 slides max. If you can’t tell the story in that space, you’re overcomplicating it.

– **Data Over Fluff**: Investors want numbers, not vague promises. Back up every claim with data.

WHAT SLIDES SHOULD BE IN EVERY DECK?

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