To view this email as a web page, click here

The 2027 AI Burnout Wave is Coming. It Will Make 2023 Look Like a Vacation. But We Can’t Slow Down.

By Jason Lemkin
Thursday, August 21, 2025 | Artificial Intelligence (AI), SaaStr.Ai

2022-2023 for many was the “Great SaaS Burnout”.

First IPOs stopped in December 2021. Then stock prices fell fast in early 2022, followed by growth rates plummeting later in the year. Layoffs swept tech companies big and small, often for the very first time ever. Founders felt the crushing weight of building in a suddenly much tougher environment. The GTM playbooks stopped working as well, and sometimes, at all. Everything was just so much harder than 2H’20-2021.

That exhaustion felt brutal at the time. You saw it all over LinkedIn. Folks quitting to be fractional execs, manage real estate, take a break, and more. But here’s the thing: it was a slow, grinding, perhaps demoralizing burnout. But mostly, things were the same. The same products, the same motions, the same game. Just a harder version of it. Difficulty level turned up, but the same game.

What we’re experiencing now in the AI Age is completely different. We’re all working far, far harder than we ever did during those post-boom years – and we’re absolutely deep into it. The capabilities of AI coding, AI agents, AI support, etc. are intoxicating. We’re all living in ChatGPT now in a way we couldn’t even imagine in 2023. The way we work has already radically changed — and it’s accelerating. The competitive advantages feel limitless.

And that’s exactly why the real burnout is still coming. And what can do you — if you want to keep up? It is what it is. You have to keep up. Or step aside.

THE AI BURNOUT IS COMING

The CRO of 2027: The Last Human Standing in GTM?

By Jason Lemkin
Sunday, August 22, 2025 | Sales

The Chief Revenue Officer may be the only GTM role that’s truly AI-proof. But one that has to evolve radically over the coming 24 months.

We’re watching AI systematically reshape every corner of go-to-market:

Customer support? Already largely automated in many cases. Intercom/Fin, Gorgias, Zendesk, Decagon and others are seeing 60%+ defection rates and AI resolving most issues.
Marketing? CMOs that aren’t AI native are panicking.
SDRs? The writing’s on the wall. We won’t need more of them.
Customer Success? AI is coming for those renewal conversations faster than you think. 90% of those check-ins and QBRs add no value anymore.
The “One Call Close” Sales Rep? The next frontier for AI.

But there’s one GTM role that’s not just surviving the AI revolution—it’s becoming more critical than ever: the Chief Revenue Officer.

THE CRO IN 2027

This edition of the SaaStr Daily is sponsored in part by Intercom

Fin—the #1 AI Agent for customer service

Fin is the best-performing AI Agent in customer service, delivering higher-quality answers and resolving more complex queries than any other AI Agent on the market. Fin is purpose-built for customer service to deliver exceptional experiences and resolves over 90% of queries automatically.

LEARN MORE AT FIN.AI

Does It Matter How Fast You Get to $1B ARR, Within Reason? Probably Not.

By Jason Lemkin
Friday, August 22, 2025 | Artificial Intelligence (AI), SaaStr.Ai

Does It Matter How Fast You Get to $1B ARR, Within Reason? Probably Not.

TL;DR: After analyzing 8 elite B2B companies that reached $1B ARR, there’s surprisingly little correlation between speed to the milestone and current market value — up to a point at least. These were all elite companies, of course. The best of the best is what it takes to get to $1B ARR.

But in the end, market TAM, business model, and post-$1B execution matter far more than how quickly you get there. Figma’s patient 13-year journey with profitability may be just as or even more valuable than Snowflake’s record 9-year sprint.

DOES IT MATTER?

The Next Great B2B IPO: Canva Crosses $3.3 Billion ARR, $42 Billion Valuation

By Jason Lemkin
Friday, August 22, 2025 | Scale

The Next Great B2B IPO: Canva Crosses $3.3 Billion ARR, $42 Billion Valuation

The Australian design unicorn is printing money (and millionaires) while building the next Adobe killer.

Fortune says Canva’s latest employee tender offer signals a 2026 IPO is coming.

TLDR: Canva just crossed $3.3B ARR at a $42B valuation, making it the most compelling SaaS / B2B IPO candidate for 2026 — for now. With 240M MAUs, 27M paid seats, and AI driving 800M monthly interactions, this isn’t just another SaaS story—it’s the democratization of design at global scale.

Canva + Databricks + Stripe? The best B2B IPOs are yet to come. We’ve just started.

THE NEXT GREAT B2B IPO

The Great AI Equalizer: How Legacy Players and Tiny Startups Are Suddenly Your Biggest Competitive Threat

By Jason Lemkin
Thursday, August 21, 2025 | Artificial Intelligence (AI), SaaStr.Ai

Why the middle of the B2B and SaaS market may be in for the biggest disruption of all.

Here’s a truth that’s keeping B2B executives up at night, even if they haven’t fully articulated it yet: AI isn’t just creating new competitive dynamics—it’s fundamentally rewiring who your real competitors are.

You have so many more now. And in some cases, the ones that were less competitive before, or in a state of decline, or just too small to matter — are back or more of a threat than ever.

We’ve all been focused on the obvious AI story: the race to build better models, the rush to integrate AI features, the scramble to avoid being “disrupted by AI.” But there’s a quieter, more insidious dynamic at play that’s reshaping competitive landscapes across B2B software.

AI is often making your most unlikely competitors suddenly viable again.

I’m talking about two categories that conventional wisdom would tell you to ignore: (1) the legacy dinosaurs everyone wrote off years ago, and (2) the scrappy 5-person startups that couldn’t possibly compete with your feature-rich platform.

Both are now punching way above their weight class. Here’s why—and what it means for your strategy.

The Lazarus Effect: When Legacy Platforms Get AI Life Support

Let’s start with the old guard. These are the platforms that have been around since the Clinton administration, built on architectures that predate the smartphone. Companies you probably haven’t considered real competition in years.

Case Study: Zendesk’s Quiet AI Renaissance.

Take Zendesk—an 18-year-old platform that many wrote off as feature-complete and innovation-stagnant. While everyone was watching the shiny new customer service platforms emerge, Zendesk quietly built some genuinely impressive AI capabilities on top of their existing infrastructure.

The result? Their AI isn’t just good—it’s making their dated platform feel surprisingly modern. Customers who might have churned to newer alternatives are now finding that Zendesk’s AI-powered workflows actually solve problems better than the “modern” alternatives without AI.

This is the Lazarus Effect in action. A great AI layer can resurrect platforms that should have been dead and buried, making them not just competitive, but sometimes superior to newer solutions that lack sophisticated AI.

The Genesys Miracle: From 1990 to $2B ARR at 35% Growth.

Want to see this dynamic in its most extreme form? Look at Genesys.

Founded in 1990—before the web browser, before Amazon, before anyone had heard of “software as a service”—Genesys spent years struggling to find its footing in the cloud era. It was the definition of a legacy dinosaur, built for an on-premise world that was rapidly disappearing.

Fast forward to today: Genesys is re-accelerating at $2B+ ARR, growing at 35% annually. They just closed a $1.5B investment round from Salesforce and ServiceNow—two companies that could have easily built competitive solutions in-house but chose to invest in the 34-year-old incumbent instead.

MORE HERE

How To Do a QBR (Quarterly Business Review) Right

By Jason Lemkin
Thursday, August 21, 2025 | Q&A

It’s a great question as QBRs have in many cases degenerated into upsell meetings, with zero value for the customer. That’s not what you want. More on that here”

QBRs (Quarterly Business Reviews) can be incredibly valuable if done right, but they’re often mishandled. Especially these days, when Customer Success so often reports to Sales.

Too many QBRs turn into boring PowerPoint presentations or thinly veiled upsell attempts, which customers hate. The goal of a QBR should be to add value, not just check a box or push more products. Here’s how to do them effectively:

1. Make It About the Customer, Not You

The QBR isn’t about showing off your product or patting yourself on the back. It’s about aligning with your customer’s goals and showing how you’re helping them achieve those goals. Start by asking:

What are their business objectives? What did they want to achieve when they signed up with you?
Are you delivering on those objectives? Be honest about where you’re succeeding and where you’re falling short.
What’s next for them? Use the QBR to understand their roadmap for the next 6-12 months and how you can support it.
And importantly — ask them ahead of time what they want to discuss. Too few do this for real. And start there.

2. Avoid the “Death by PowerPoint” Trap

No one wants to sit through a 30-slide presentation. Instead:

Focus on Outcomes: Highlight key metrics that matter to the customer (e.g., ROI, efficiency gains, cost savings).
Be Visual: Use simple, impactful visuals to tell the story. A few charts are better than a wall of text.
Keep It Short: Aim for 30 minutes max. Respect their time.

3. Don’t Make It a Sales Pitch. Please.

This is critical. If your QBR feels like a thinly disguised upsell, you’ll lose trust. Instead:

Add Value First: Share insights, best practices, or benchmarks that are relevant to their business.
Upsell Organically: If there’s a natural opportunity to expand the relationship, frame it as a way to help them achieve their goals—not as a way to hit your quota.

HOW TO DO A QBR

The Latest 20VC+SaaStr: Databricks Hits $100B, CoreWeave’s $11B Debt Gamble, and Why We’re All Living in the AI Bubble

By Jason Lemkin
Friday, August 22, 2025 | Artificial Intelligence (AI), SaaStr.Ai

The latest 20VC x SaaStr episode with Harry Stebbings, Jason Lemkin, and Rory O’Driscoll is here! The team is discussing Databricks’ $100B valuation, the coming IPO tsunami, CoreWeave’s massive debt raise, AI infrastructure spending that could hit trillions, the return of SPACs as a bubble signal, and why AI tool consolidation will happen faster than anyone expects.

Bottom Line Up Front

Harry Stebbings: “We’re seeing the biggest wealth transfer in tech history unfolding before our eyes. When Databricks hits $100B and Andreessen could make $30B on a single deal, we’re not just in a bubble—we’re in a generational moment where the next wave of IPOs could make 2021 look like the appetizer.”

Jason Lemkin: “I think we’re all going to live in AI 24/7 and use 10 times the tokens and 10 times the compute in 24 months. The math is staggering—if we need 200x more infrastructure, how do we even finance that? But here’s the thing: we’ve already automated 5 humans with 10 AI agents at our small team. This isn’t theoretical anymore.”

Rory O’Driscoll: “All this depends on 3-5 m\ore years of continued AI capex expansion. If that’s the case, everything works. If not, all bets are off. We’re way out on the risk curve, and the only thing between us and Armageddon is AI adoption continuing at this pace.”

THE LATEST 20VC+SAASTR

Dear SaaStr: What Are the Different Types of “Commits” Each Sales Rep Should Make?

By Jason Lemkin
Friday, August 22, 2025 | Artificial Intelligence (AI), SaaStr.Ai

The forecasting stages for a rep typically break down into three key categories: **Commit**, **Most Likely**, and **Best Case**. Bigger companies sometimes use more categories, but it’s tough to have consistency in a start-up pipeline forecast if you use more than these 3 or so.

Here’s how these stages work and what they represent:

1. “Commit”: (90%+ Chance Close)

This is the deal the rep is absolutely confident will close. It’s the most reliable part of the forecast and should have a very high probability of closing—think 90% or more. These are deals where all the boxes are checked: contracts are in final stages, the buyer has confirmed intent, and there are no major risks left. If a rep misses their commit, it’s a red flag. This is the number you should hold them most accountable for.

2. “Most Likely”: (50%-90% Chance Close)

This is the realistic forecast. It includes the commit deals plus others that have a solid chance of closing but might still have some risks or dependencies. These deals are usually in the later stages of the pipeline, but there might be a few hurdles left to clear, like final approvals or budget sign-offs. This number should be your baseline expectation for the quarter.

3. “Best Case”: (10%-20% Chance Will Close)

This is the upside potential—the deals that could close if everything goes perfectly. These are often earlier-stage opportunities or deals where the buyer has expressed strong interest but hasn’t fully committed yet. Best case is where you factor in optimism, but you should never rely on it to hit your targets. It’s more about understanding the total potential upside in the pipeline.

The key to making these stages work is **discipline and intellectual honesty**.

Reps need to be ruthlessly honest about where their deals stand.

If a deal is in commit but doesn’t close, you need to dig into why. Was it truly ready to be committed? Did the rep overestimate their confidence? Similarly, if a deal slips from most likely or best case, you need to understand what went wrong and adjust your forecasting process accordingly.

A great practice is to retroactively compare a rep’s forecasted stages to actual outcomes. Over time, this helps you understand how accurate each rep is at predicting their own pipeline and where they might need coaching. It’s all about building predictability and accountability into the process.

THE DIFFERENT "COMMITS"

644 Emerson St. Suite 200, Palo Alto, CA, 94301

If you'd like to stop receiving the SaaStr Daily, click here