Every founder knows they need enterprise customers. Most focus entirely on how to sell to them.
The founders who are succeeding right now are thinking differently. They are not just pitching to the enterprise — they are building with them. And in a world where large corporations are under pressure to deploy AI faster than they can build, that distinction matters.
Here is what we are seeing across our portfolio, and what it means for how you should be approaching your most important relationships.
“The best enterprise relationships start with a founder who genuinely wants to understand how the business works, where the friction is, and what it takes to make the technology stick. When you align around the impact an enterprise creates in the world, and not just the problem you are solving, you stop being a vendor and start being part of how they deliver on their mission. That is what separates the companies that get embedded from the ones that get replaced,” says Managing Director Mike Hayes.
For most of software’s history, the enterprise was a destination. You built something, proved it out in the mid-market, and eventually graduated to the Fortune 500. The enterprise sales cycle was long, the procurement process was demanding, and the relationship was largely transactional once you were in.
That model is under pressure. Many large enterprises are actively looking for startup and ScaleUp partners to co-develop and pilot AI capabilities in areas where they cannot build fast enough on their own. Startups bring speed and targeted technology. Enterprises bring data, distribution, business context, and budget. The overlap between those things is where the most interesting partnerships are forming right now.
What this means in practice: Enterprise buyers are increasingly evaluating not just your product, but whether they want to be in a long-term working relationship with you. Whether you understand their constraints. Whether you can move fast enough to be useful. Whether the relationship creates value beyond the contract.
The founders who recognize this early tend to treat enterprise relationships less like a sales motion and more like a partnership. They share early, co-design where possible, and give customers a degree of ownership over what is being built.
CrewAI* is one example from our portfolio. When João (Joe) Moura launched the multi-Agent orchestration platform, he treated large companies as co-builders rather than just buyers. Within six months of launching, CrewAI had signed 150 enterprise beta customers, including PwC, IBM, and NVIDIA, who were active participants in shaping the platform, not just evaluating it. Today, CrewAI reports powering more than 1.4 billion agentic automations across enterprise customers, running approximately 450 million Agents a month.
Promptfoo* took a complementary approach. The AI security testing platform started as an open-source project and grew by embedding itself into how enterprise engineering teams worked. By the time raised its $18.4M Series A round led by Insight Partners in July 2025, its tools were in use by more than 30 Fortune 500 companies.
From that point, Insight worked closely with the team — connecting them with enterprise partners to build pipeline, facilitating connections at key industry events, and providing direct support to help close late-stage deals with some of the world’s most recognizable companies. In March 2026, OpenAI acquired Promptfoo to integrate its capabilities directly into OpenAI Frontier. The company had raised $23 million in total funding.
Both companies earned deep enterprise relationships not primarily through sales execution, but by becoming genuinely useful inside their customers’ workflows before the formal relationship was fully defined.
Most founders do not have direct access to the enterprise decision-makers who matter most, and many underestimate how much that gap costs them.
Senior enterprise leaders — the CIOs, CTOs, and division heads who can greenlight a meaningful pilot or advocate for a deeper partnership — are not typically reachable through standard outbound. They are at working sessions, private dinners, and curated events.
This is one of the concrete benefits of being part of a strong investor ecosystem. At Insight, we connect our founders directly with senior enterprise leaders across our network — not to hand you a lead, but to create conversations where both sides walk away with something. For the enterprise, that means early access to technology that can move their business forward. For the founder, it means relationships with organizations that can accelerate the milestones that matter most: landing your first Fortune 500 customer, expanding into a new geography, or breaking into an industry where trust takes years to earn on your own.
“Some of the most valuable real estate in enterprise software is a seat at the right table. What gets you there is trust, and trust takes years to build. Our job is to give founders a shortcut to that trust by putting them in rooms they could not get into on their own, with people who are genuinely open to what they are building. But it cannot be a one-way street. Relationships are still the core of business, even with AI,” says Hayes.
“Our job is to give founders a shortcut to that trust by putting them in rooms they could not get into on their own, with people who are genuinely open to what they are building.”
Last year, Insight Partners for Enterprise partnered with ServiceNow on a Founders Day, bringing eleven portfolio founders and CEOs directly to ServiceNow‘s offices in Santa Clara for face-to-face meetings with their senior leadership. Managing Director Teddie Wardi shared Insight’s perspective on agentic AI. Portfolio founders showcased how their solutions drive outcomes across ServiceNow’s ecosystem. And ServiceNow’s leaders got direct exposure to builders working on AI, security, automation, and data infrastructure — resulting in ServiceNow’s $7.75B acquisition of Armis.
ServiceNow‘s Hala Zeineput it directly:
“The most enduring partnerships are built on innovation meeting real-world needs. And conversations like these are where it all begins.”
Enterprise executives are also increasingly sitting on startup boards, advising companies in their space, and engaging through industry networks that many early-stage founders have not yet accessed. The question worth asking is: How plugged in are you to that world?
Before getting to the relationship advice, it helps to understand what is happening on the other side of the table. Enterprise buyers are not just evaluating whether your product works. They are managing risk, and they have a long list of questions to get through before anyone signs anything.
They will ask about data storage, security protocols, regulatory compliance, AI accuracy, model governance, and IP ownership. They will want a proof of concept with clear success criteria. They will involve IT, legal, finance, and procurement — not because they are slow, but because these functions are what keep them compliant as they move fast.
Successful enterprises are deploying AI quickly and safely, and they need founders who understand that speed and governance are not in conflict. Getting buy-in across these stakeholders is not a bureaucratic hurdle. It is how you make sure the technology actually solves a business problem, not just a technical one.
This is not a reason to avoid enterprises. It is a reason to prepare differently. The founders who move through enterprise procurement quickly are often the ones who have anticipated these questions, have the documentation ready, and can demonstrate ROI in terms that the buyer can take to their own leadership.
Here is what we consistently see work across our portfolio when founders are building, not just selling, enterprise relationships.
1. Propose a co-pilot, not a sale. When you are in early conversations with a strategic enterprise target, look for one team inside that company willing to build something with you rather than just buy something from you. Structure it like a real proof of concept (PoC): Define success criteria upfront, set business outcome benchmarks, and make clear what ROI looks like. A joint pilot with shared ownership changes the dynamic. They become a champion. You get access to real-world constraints that make your product better, and you leave with the data you need to close the next deal.
2. Invest in the relationship. Most enterprise deals start with one person who opens the door. The strongest partnerships grow beyond that. When you take the time to build connections across the organization — with the executive sponsor, the team closest to the problem, and the people who will champion adoption day to day — you create the conditions for real adoption, natural expansion, and renewals that do not have to be fought for. The broader your relationships inside an account, the more resilient and valuable the partnership becomes for both sides.
3. Do your homework and adapt your approach. Before any enterprise conversation, understand what is happening inside that organization: their priorities, their constraints, their appetite for working with startups, and which regulatory or compliance requirements will shape their evaluation. A CIO in the middle of a major transformation initiative has a completely different headspace than one operating in steady state. The same product, pitched the right way at the right moment, lands differently.
Revenue is the obvious outcome of an enterprise relationship. There are others worth keeping in mind.
Promptfoo is a recent example. OpenAI did not acquire them because they ran a formal process and found them. They acquired them because the enterprise world had already adopted their technology at scale. Deep product integration into your customers’ workflows is a meaningful acquisition signal, built through relationships, not pitches.
Large enterprises have R&D budgets, proprietary datasets, and distribution that would take a smaller company years to build independently. A well-structured partnership can provide access to all three. The tradeoff, roadmap alignment, and customization are often worth it.
An enterprise customer who becomes a sell-through partner can open market segments that sit outside of your current reach. That outcome is earned when your product fits naturally into what they already sell — giving their team both the incentive and the context to bring it into customer conversations.
The right enterprise executive in an advisory role brings more than a name on a website. They bring pattern recognition, honest feedback, and introductions. And the best ones are often converted from relationships where you already proved the value.
“Revenue and pipeline, you can see. What is harder to see, and harder to build, are the relationships in the market that help you across the full spectrum of leading a company.”
“The thing that separates elite founders is understanding that the most valuable opportunities are not always the obvious ones,” says Hayes. “Revenue and pipeline, you can see. What is harder to see, and harder to build, are the relationships in the market that help you across the full spectrum of leading a company. The enterprise leader who gives you honest feedback on your roadmap. The connection that helps you find your next great hire. The conversation that helps you see around a corner you did not know was there. When you build those relationships, you are not just growing a business. You are creating value in the world together by working as a true team that knows everyone’s goals and is committed to mutual success.”
AI has created real urgency for large enterprises to find startup and ScaleUp partners who can help them move faster than they can on their own. The founders who capitalize on this will not have won on product features alone. They will have built the relationships early, before the formal process started, before the press releases, and in many cases before anyone else was in the room.
Editor’s Note: Insight has invested in Armis, CrewAI, and Promptfoo.
Many of the lessons Mike Hayes shares in this edition are explored further in his book, Mission Driven: The Path to a Life of Purpose, which you can find here.
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