Three months ago, Leaders Fund Co-Founder Gideon Hayden ran a little experiment.
He looked at the ages of founders who had started ten post-ChatGPT AI startups like Anysphere and ElevenLabs, and then looked at the ages of the founders behind older giants such as Stripe and SpaceX. The average founder age had dropped from 31 to just 25.
“Having the best product is probably 15 percent of the battle.”
Gideon Hayden, Leaders Fund
In thoughts shared on LinkedIn, Hayden said that either “some of these people are frauds,” or “there is a new generation of AI startup founders that are starting successful companies way younger than we’ve seen in the past, and doing it with much less capital and fewer people.”
AI startups are scaling faster and younger than ever. But early speed is not the same as long-term survival. Winning over consumers with a clever product demo is one thing, but convincing a regulated enterprise to stake its reputation and data security on a ten-person team is another.
There are several notable startups that have been rumoured or stated to have reached $100 million in annual recurring revenue very quickly and with relatively small teams by leaning on product-led growth rather than the standard enterprise procurement process.
But crossing the bridge to true enterprise contracts might be a different ball game. So, BetaKit asked four investors what it will take for today’s AI founders to survive the hype, win over enterprises, and build companies that last.
Plan beyond the rush
Aspenwood Ventures’ Managing Director Lars Leckie regularly advises founding teams selling into large institutions, and he describes today’s procurement climate as a “Wild West.”
Many already Fortune 500s are testing AI tools in ways that bypass the usual guardrails: security reviews, vendor assessments, and compliance hoops. According to a recent report from LayerX, 91 percent of AI tools inside enterprises operate without any IT oversight.
Leckie says that many AI companies are landing big contracts because enterprises have relaxed procurement rules in order to capitalize on AI.
“Friction has been removed from the cycle,” Leckie said.
But that won’t last. Leckie cautioned that enterprises will eventually recalibrate, and today’s AI experiments will be pulled back into the standard procurement process.
Leckie said founders therefore need to start “putting the scaffolding in place to be ready for that change” and get ready to win deals after the gold rush.
Prove your company can endure
Paul McKinlay, Executive Managing Director and Head of CIBC Innovation Banking, is the first to say that enterprises prefer to be fast followers rather than first movers.
“It’s impossible for big enterprises to ignore AI,” McKinlay said. “At the same time, they still have to be very protective of their data assets and customer information.”
That tension means startups face a tougher test than they might expect. Buyers aren’t just evaluating the product; they are measuring whether the company itself can survive over time.
Elizabeth Weil, Founding General Partner at Scribble Ventures, said one of the strongest signals to enterprises comes from founder-led sales.
“The way someone sells their vision to investors communicates a lot about their sales acumen,” Weil said. “Founder-led sales is critical, and you can see a high degree of know-how across many factors like their speed, clarity of communication, conviction, and networking. All of these translate well when selling into any industry.”
But communication alone doesn’t guarantee resilience. Enterprises also want assurance that the company won’t falter if key people walk away. Fast growth and small teams can create distinct risks for enterprise partners.
“If you have eight people and one or two of the key leaders leave, that’s a bigger issue for a buyer,” McKinlay added.
Add in regulatory risk, compliance demands, and long implementation cycles, and the question becomes whether the startup has the depth to endure.
“Having the best product is probably 15 percent of the battle,” Hayden said. “It’s necessary, but not sufficient to win a deal.”
Build credibility with backers
Enterprise procurement can stretch from weeks to months, and during that cycle, buyers are measuring product fit, as well as whether a team has the credibility to support them over the long haul.
“The thing that most startups in the early days lack is credibility,” Hayden said. “They’re young, they’re unproven. No one knows who they are.”
This is where the composition of a startup’s backers can tip the scales. When enterprise buyers see reputable investors or financial institutions at the table, it signals that someone has already done the hard diligence.
“If you have credible, top-notch VCs, as well as a bank like us around the table, it means you have some financial diligence behind you already,” McKinlay added.
Patience is also a necessity. Leckie pointed to Calgary-based AI startup Smart Access as one example of a team that scaled the right way—growing contracts step by step from $300,000 to $2 million before recently landing its first contract with an enterprise customer.
Big enterprise wins bring heavy onboarding, compliance, and support costs, Leckie said. Without the right investors and advisors, those costs can sink a young team.
Even with strong backers, founders can sabotage themselves by overpromising or underestimating what it takes to serve enterprise customers. Investors and financial partners like Hayden and Leaders Fund view how teams forecast resources as a key test of discipline.
“When I see companies that are doing really well, but they believe that they’ll never have to invest in things like account management, sales, or customer support because they’re an AI company, that’s a red flag to me,” Hayden said.
For now, small AI teams are enjoying rapid adoption and marquee logos. But the real test will be whether they can scale from shadow IT and credit-card pilots to enterprise systems of record.
“It’s easy to get really excited about a really cool demo or what AI can do, but you need to be customer obsessed,” Hayden added. “I think that that’s true both on the technology side, but also in how one might sell to an enterprise.”
The procurement hump is waiting. The startups that clear it will be the ones that combine speed with resilience, credibility, and the unglamorous work of enterprise sales.
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Feature image courtesy of Unsplash. Photo by Charles Deluvio.