How Glean & Huntress Hit $100M ARR: Two Founders, Two Paths

One founder left a $3B unicorn at its peak. Another slept in a Ford Focus trunk to save runway. Both hit $100M ARR. The Product Market Fit Show's Web Summit Vancouver panel with Arvind Jain and Kyle Hanslovan delivers the rawest, most practical founder lessons you'll hear this year.

Key Facts

• Glean's seed raise: $15M raised before a single dollar of revenue (Arvind Jain)
• VC rejections (Huntress): At least 60 VCs said no before Kyle closed funding (Kyle Hanslovan)
• Glean's pre-revenue period: Two full years building before generating any revenue (Arvind Jain)
• Huntress founding context: Kyle had three kids aged 5, 9, and 11 when he started Huntress (Kyle Hanslovan)
• Rubrik growth: Grew from 500 to 1,500 employees in one year — but lines of code stayed flat (Arvind Jain)

Why Arvind Jain Left a $3B Unicorn to Start From Zero

Arvind left Rubrik at its peak because he identified a problem no product solved: enterprise search. As Rubrik scaled from 500 to 1,500 employees in a single year, productivity collapsed — and Arvind, a search engineer by training, saw a massive unsolved gap in the market.

Most founders start companies out of necessity or frustration. Arvind Jain did something rarer — he walked away from a $3B company he co-founded at the moment of its greatest success to solve a problem he couldn't stop thinking about. At Rubrik, headcount tripled in a year, but output didn't. The culprit was information chaos across hundreds of SaaS systems.

When Arvind tried to buy a solution, none existed. That absence became Glean. He initially explored building it inside Rubrik, but quickly realized it needed to stand alone. The insight was simple but powerful: if every person at a fast-growing company complains about not finding information, the market is real — no TAM spreadsheet required.

His approach to market validation was instinct-driven, not analytical. As he explained to the Web Summit audience, 'Every single person in my company, every single friend of mine who worked at other companies — they would all talk about how hard it was to find things inside their own companies.' That signal was enough to go all in.

"I don't think we get to actually be in this space where we can say that, yes, we have this product market fit. Now this is our product, and now go and scale. You have to continuously iterate." — Arvind Jain

"If you see a problem that you believe a large number of people have, that's enough. I don't need to actually go and quantify that with dollars." — Arvind Jain

Kyle Hanslovan's Path: 60 Rejections, a Ford Focus, and a New Market

Kyle built Huntress with no pedigree investors would recognize — no famous logos, no Fortune 500 customers, and a service-heavy model that confused VCs. He survived by staying capital-disciplined, sleeping in his car to preserve runway, and finding his first customers at a single trade show.

Kyle Hanslovan came from the NSA, where he spent years on offensive cyber missions. His mission with Huntress was to bring enterprise-grade security to the businesses that couldn't afford it — the ones below the Fortune 500 poverty line, as he describes it. It was a compelling mission. It was a brutal fundraising story.

At least 60 VCs passed. The problem wasn't just the market — it was Kyle's pitch. 'I didn't know how bad I was at pitching,' he told the Web Summit crowd. Investors heard 'services' when he said 'humans in the loop.' They saw 60% gross margins as a ceiling, not a feature. The gap between what Kyle was building and what investors heard took years to close.

The breakthrough came at a trade show for outsourced IT providers — managed service providers who each served 20 to 200 small businesses. Kyle and his team maxed their credit cards to get there, slept in the car to stretch runway, and walked away with their first real customers. The flywheel started spinning and never stopped.

"You name a Silicon Valley investor. They have told me politely and very directly at times — I think it was like, 'Go fuck yourself.'" — Kyle Hanslovan

"Even though it's solved in your brain, some of your biggest hurdles might actually be how you sell your own story." — Kyle Hanslovan

• 60+ VC rejections before closing funding
• First customers came from a single managed services trade show
• Credit cards maxed; car used as accommodation to preserve capital
• Technical founders must also learn to sell their own story clearly

Go Big vs. Stay Lean: Two Valid Approaches to Early-Stage Building

Glean went big from day one — large team, long build cycle, no revenue pressure. Huntress validated through brutal frugality and market feedback. Both worked. The choice depends on founder conviction, capital access, and whether the product requires deep infrastructure before it can prove value.

The lean startup methodology dominates founder circles — validate fast, ship early, iterate. Arvind deliberately chose a different path for Glean. Enterprise search requires deep integrations across hundreds of SaaS systems. There was no shortcut. 'We were alone in the market,' he explained. 'We were the first product in AI, in enterprise gen-AI. And before others come into the market, we wanted to be there.'

Kyle took the opposite road — not by choice, but necessity. Every decision was filtered through an ROI lens. Sleeping in the car wasn't grind culture performance; it was the logical trade-off when cash was finite and the alternative was burning runway on a hotel room instead of go-to-market.

The shared lesson isn't which method is right — it's that both require intentionality. Arvind's approach worked because he had the capital and conviction to sustain a long build. Kyle's worked because he stayed ruthlessly aware of his trade-offs. As Kyle put it: 'It's not just about infinite grind. You need to actually have some level of basic ROI analysis for just about everything.'

"For us, LandGrab was actually important because we were alone in the market. We were the first product in AI, in enterprise gen-AI. And before others come into the market, we wanted to be there." — Arvind Jain

"I'm not saying celebrate grind culture. But I'm saying if you do the research the right way, you can take that level of risk." — Kyle Hanslovan

How to Know When You Have Product-Market Fit (Hint: You Probably Won't)

Both founders admit they didn't recognize product-market fit when they had it. Kyle was too conditioned by rejection to trust early traction. Arvind still considers Glean in the search — because in a fast-moving AI market, fit is a moving target, not a finish line.

Product-market fit is the most discussed concept in startupland and possibly the hardest to self-diagnose. Kyle's tell was predictability: 'This week I could see X number of deals, and next week it would be plus two. Then the following week it'd be plus four.' But even with that signal, he didn't believe it. Years of bootstrapping and rejection had made him too paranoid to trust his own success. It took another founder explicitly telling him he had PMF before he accepted it.

Arvind uses a different lens. Glean's first proof point was internal — 50 employees used the product daily, and new hires began onboarding themselves without hand-holding. When the team started raving about the experience, that was the signal. 'That's the first time I've been to a company where I was able to onboard myself,' employees told him.

But Arvind's definition of PMF has evolved. In an AI market where work habits shift constantly, he sees fit as an ongoing discipline, not a milestone. The moment you declare victory and stop iterating, you're already falling behind.

"I almost couldn't believe my own success. Even when I had it, I didn't know." — Kyle Hanslovan

"I still feel that we're still looking for it. You have to continuously iterate and keep learning how people's work habits change." — Arvind Jain

Final Advice From Two Founders Who Made It to $100M ARR

Arvind's advice: believe in your idea and don't give up. Kyle's advice: ship earlier than you think you should — if it delivers value, even broken, it's good enough. Value is validated when someone pays you, even a small amount.

When Pablo asked for one piece of advice each, the answers were simple, direct, and complementary. Arvind's came from a place of long conviction: 'Work hard and actually believe in your idea. Don't give up.' It sounds basic. Coming from someone who raised $15M into a category investors actively told him to avoid, it lands differently.

Kyle's advice was tactical: 'You can ship much earlier than you believe. Even if it's busted, broken — if it's delivering value, it's probably good enough. And value is measured by people giving you a dollar or a nickel or whatever.' The bar isn't perfection. The bar is whether someone will pay, even minimally, because they get something from it.

Together, the advice maps a simple framework: have conviction, preserve capital, ship before you're ready, and let paying customers — not your own doubts — tell you whether you've found something real.

"Work hard and actually believe in your idea. Don't give up." — Arvind Jain

"You can ship much earlier than you believe. Even if it's busted, broken, if it's delivering value, it's probably good enough." — Kyle Hanslovan

Glean vs. Huntress: Two Paths to $100M ARR