So it’s a bit funny, when we started SaaStr we rarely talked about the stage beyond $100m ARR.

That’s what it took to go big and IPO.  HubSpot, Box, Zendesk, etc. all IPO’d at around that stage.  Growing very, very quickly.  But around then.

Helping you get to $100m ARR with less stress and more successful was our goal at SaaStr.

But time has gone on, and Cloud and then AI have made everything so much bigger.  And the IPO bar has gone up.  Now it’s 50% growth at $500m ARR, not 50%+ at $100m ARR.

And I’ve also gotten a chance to see a lot of B2B start-ups get to $50m-$100m fairly quickly and then .. decelerate.  Often very, very quickly.

And that now is my #1 worry investing.

Whether they’re going to stall out around $100M ARR.

And here’s the thing — I used to think this was basically impossible.

The data backs this up. According to recent SaaStr analysis, top-quartile VC-backed startups at $100M ARR are only growing 22% — well below the 40% threshold needed for a healthy IPO path. And 80% of VC-backed startups aren’t growing fast enough to raise another round.

What Stalls Growth Around $100,000,000 ARR

1. Multi-Product Isn’t Optional Anymore — And You Need It Earlier Than Ever

The days of riding a single product to $500M ARR are essentially over for most categories.

Your customers are consolidating vendors. Your competitors are expanding their surface area. The “best of breed vs. suite” debate? The suites are winning more often than not.

Here’s the research that should get your attention:

Procore’s lesson: At $1.2B+ ARR, 60% of customers now buy 3+ products. The average customer uses 3-4 products, with large enterprises using 5-6. Their ex-CRO Dennis Lyandres is emphatic: “The days of single-product success in SaaS are numbered.” What’s fascinating is that Procore didn’t start seriously implementing their multi-product strategy until years 14-15. The regret? Not doing it sooner.

Datadog’s dominance: As of Q3 2025, 84% of customers use 2+ products (up from 83% a year ago), 54% use 4+ (up from 49%), and 31% use 6+ (up from 26%). Even 16% of customers are using 8 or more products. New logo annualized bookings more than doubled year-over-year, with new customers landing bigger from day one. That’s not upselling. That’s how buyers want to buy now.

HubSpot’s transformation: In Q3 2025, 43% of Pro+ customers subscribe to all three core hubs — up 4 points year-over-year. They’ve grown to nearly 279,000 customers with $810M in quarterly revenue. As their CEO Brian Halligan put it with the “Clydesdale Rule” — one Clydesdale can pull 1,000 pounds, but add a second and together they pull far more than 2,000.

Box’s renaissance: Multi-product customers show 125% NRR versus 90% for single-product customers. Their CEO Aaron Levie’s top regret at SaaStr Annual? Not going multi-product earlier.

The rough rule: You need a second product firmly in place by 10,000 customers or $100M ARR — whichever comes first. That probably means launching by the time you have 5,000 customers. If your ACV is low, that could be as early as $10M ARR.

The companies breaking through are the ones who started thinking about multi-product at $20-30M ARR, not $100M.

2. You Have to Tap Into AI Budget — That’s Where ALL the Incremental Spend Is

Here’s the uncomfortable truth about enterprise software spending right now: Almost all the incremental budget is flowing to AI.

The data is staggering:

Global AI spending is approaching $1.5 trillion in 2025 according to Gartner, with projections to exceed $2 trillion by 2026. Meanwhile, overall IT budgets are only growing 1.8% (barely keeping pace with inflation).

AI is capturing 30% of total IT budget growth. ISG’s 2025 study found that with an average IT budget increase of $11.5 million, AI accounts for $3.4 million of that increase — nearly a third. AI spending is growing 5.7% while total IT budgets barely move.

Enterprise AI budgets are growing 75% year-over-year according to Andreessen Horowitz’s survey of 100 enterprise CIOs. As one CIO put it: “What I spent in 2023 I now spend in a week.”

AI has graduated from innovation budgets to core IT spend. Last year, 25% of AI spending came from experimental innovation budgets. Now that’s dropped to just 7%. AI is no longer a pilot — it’s a line item in core business budgets.

“Next year, we’re going to spend more on software with GenAI in it than software without it” — that’s Gartner’s John-David Lovelock. Think about that. Just four years after GenAI became available, it will dominate enterprise software purchasing decisions.

If your product doesn’t have a compelling AI story — not AI washing, but genuine AI-powered value — you’re fighting for flat or shrinking budgets while your competitors with strong AI positioning are capturing all the growth dollars.

The Playbook for Breaking Through

So what do you do if you’re a founder staring down this $100M ceiling?

Go multi-product faster than feels comfortable. Follow the Toast/Procore playbook: identify key control points in your customers’ workflow and build from there. Toast’s pivot from a payments app to a comprehensive back-of-house management system is why they’re worth $9B+ today. SaaS companies selling more than one solution increase retention by nearly 20% — platforms with 4+ solutions have 80% better retention than single-product companies.

Find your AI angle — and make it real. 67% of projected AI spending in 2025 comes from enterprises embedding AI capabilities into core business operations. Software development has seen a step-change in AI adoption. One CTO reported that 90% of their code is now AI-generated through tools like Cursor and Claude Code, up from 10-15% just 12 months ago with older tools. Where does AI genuinely make your product 10x better? That’s your path to new budget.

Think platform, not product. The companies breaking through $100M today are the ones building ecosystems. Datadog now has 15 AI-native customers spending more than $1 million annually (up from essentially zero a year ago) and 32,000 total customers. Procore and Toast have become the “operating system” for their respective industries. Single products hit ceilings. Platforms keep growing.

Land bigger, earlier. The math on getting to $200M+ is way easier with $500K average ACVs than $50K. Procore went from construction project management to financial management as their “Act Two” specifically because it gave them access to larger budgets and more strategic relationships.

The $100,000,000 ARR Ceiling is Real

The $100M ARR ceiling is real, and it’s catching a lot of good companies off guard.

But it’s not inevitable. The founders who recognize the game has changed — who go multi-product earlier, who tap into AI budgets, who build genuine platforms — are still breaking through.

The question is whether you’re building for the SaaS playbook of 2019 or the one that actually works in 2025.

The ceiling is only there if you let it be.

Related reading:

• When to Go Multi-Product in SaaS
• The Truth About Building a Successful Multi-Product Strategy: 5 Key Learnings from Procore
• How, When and Why to Launch a Second Product: A Deep Dive with Dharmesh Shah