Introduction

What does it really take to turn a B2B software startup into a category-defining unicorn? On this episode of “The Science of Scaling,” host Mark Roberge sits down with Frederic Kerrest, co-founder of Okta, to deconstruct the journey from early sales hustle to a successful IPO. Kerrest shares hard-won lessons on how technical founders can embrace sales, the importance of early customer relationships, and how the future of AI will reshape enterprise go-to-market strategies.

Apple | Spotify

Founder Selling: The Relentless Hustle of Early Go-to-Market

In the earliest days, sales isn’t just a department—it’s a founding team responsibility. Kerrest and co-founder Todd McKinnon didn’t just wait for ideal customers to magically appear. As Kerrest puts it, “Your number one job as an entrepreneur anyway is to sell. If you are not comfortable selling, you need to get comfortable selling.”

Instead of hiding behind email, Kerrest leaned heavily into warm outreach: alumni networks, LinkedIn connections, and even university databases formed the backbone of his prospecting. The tactic? Do what great sellers do: “Go out and talk to people and understand…show them drawings, show them pictures, show them documents, show them the product.”

But these weren’t pushy cold calls. Kerrest emphasized a value-add approach—offering insights about trends in AI or cybersecurity, for example, before even mentioning his product. This two-way street made prospects more engaged and positioned him as a consultative partner, not just a vendor.

The Art of Customer Discovery and Qualifying Demand

Early sales is as much about learning as it is about closing. The Okta team’s approach speaks to classic product-market fit discovery: set targets for monthly customer conversations (in Okta’s case, 18 per month), map out the real pain points, and never be afraid to ask for early buy-in—even before the product is built. 

As Mark Roberge highlights, the litmus test isn’t just “would you use this?” but “would you write me a check—even a letter of intent—for this?” This separates false positives from real early adopters who feel the pain acutely enough to pay. 

Kerrest also borrows from proven selling methodology, recommending frameworks like MEDDIC (Metrics, Economic buyer, Decision criteria/process, Identify pain, Competition), which helps founders diagnose stakeholder motivations, decision processes, and internal champions. The goal is clarity—knowing which opportunities are worth pursuing and which aren’t.

Scaling Sales: Building the Right Team and Culture

Once product-market fit emerges, founders face a critical transition: hiring and scaling a sales team. Kerrest advocates for hiring in threes—“They’re competitive, you’ll learn from different selling styles, and you’ll quickly calibrate quota expectations.” This playful rivalry fuels productivity and helps founders see what really works in the field.

But even after onboarding professional sellers, founders must stay close to the action. The risk of disconnection is real—sales teams, focused on quotas, might pressure for features that are one-off solutions, distracting precious engineering resources. “You need to be the Fennec fox, not the alligator—small mouth, big ears,” says Kerrest. Listening directly to customers helps founders stay tuned to genuine market demand versus noise.

Sales pipeline, too, isn’t just marketing’s job. Experienced field reps bring decades of relationships—often generating pipeline through trust and their own networks. Don’t delay hiring until inbound leads are overflowing; good salespeople can—and should—create opportunities.

The Next Frontier: AI’s Role in the B2B Sales Landscape

Even with accelerating advances in AI, Kerrest is confident that enterprise software sales—especially six-to-seven-figure deals—will remain a deeply human endeavor. AI will power more efficient qualification, note-taking, and process automation, liberating sellers from administrative grind. But the essence of high-stakes deals? People buy from people.

As Kerrest observes, while foundational AI innovation may accrue to hyperscalers, the complexity of modern security, privacy, and access management in an AI world spells massive opportunity for SaaS startups. “It’s almost like the matrix just went up a dimension,” he remarks, challenging founders to build for environments with more data, risk, and requirement for trust than ever.

Giving Back and Building for Good

Beyond scaling unicorns, Kerrest is passionate about using success to drive impact. Okta for Good and personal initiatives like donating book proceeds to youth-focused nonprofits are testament to his belief: tech founders can and should give back, especially as federal and local funding recede.

Conclusion

The Okta playbook, as unpacked on “The Science of Scaling,” is clear: Early go-to-market is scrappy, founder-led, and deeply connected to customer pain. Success at scale comes from systems, strong team culture, and unrelenting focus on qualifying, listening, and adapting. And no matter how smart the technology gets, trust and relationships will always be at the heart of transformative B2B growth.  

Listen to the full episode for even deeper insights, and discover the frameworks and strategies to scale your own SaaS venture.

~~~~~

Note: The insights shared in this podcast were initially distilled through advanced AI summarization technologies, with subsequent refinements made by the writer and our editorial team to ensure clarity and engagement.

About "The Science of Scaling" Podcast

Every week during a season, host Mark Roberge—co-founder and Managing Director at Stage 2 Capital and a senior lecturer at the Harvard Business School—interviews some of the tech industry's most successful and renowned leaders and managers in the areas of sales growth and Go-to-Market strategy. This is a HubSpot for Startups original podcast, and part of HubSpot's Podcast network. It's available on Apple, Spotify, and anywhere you get podcasts.