It’s one of the most important decisions for any early-stage startup. Who are you actually going to sell to? Your choice of target customer will affect every facet of your business, from your investor relationships to your hiring strategy and cash flow.

And there can be few harder tasks for an early-stage startup than hammering on the doors of some of the world’s largest companies. Managing dozens of stakeholders from different divisions and geographies during a sales process is tough enough. But the due diligence and vetting also goes to another level, given enterprises’ understandable concerns about cybersecurity and risk management.

But as Flip’s Fabian Winkels observes, “Successful enterprise models are very rewarding.” Enterprise software remains one of the most commercially successful and enduring technology categories. So how can founders capitalise on such a massive market, and get ready to sell into the biggest businesses? In this article we’ll give you opinions from people who’ve been on both sides of the deal, helping you identify the mistakes to avoid and give your startup the best chance of breaking into those enterprise deals.

Flip is an AI-native employee experience platform used by many global organisations. Fabian joined Flip’s leadership team in 2024 and leads functions including strategy, marketing, and revenue operations. What made the enterprise segment a logical choice for Flip? “Building trust with customers and closing deals is harder, but average contract values are also attractive. And, once a deal is done, the opportunities for expansion are huge, and customer relationships are much stickier,” Fabian reflects.

Many early-stage founders will test and experiment to understand whether their business is likely to work for the enterprise segment. But not all business models are a natural fit for large enterprises. How can founders tell whether their proposition will work in global organisations? “Consider the target user of your product,” advises Fabian.

Even if your ambition is to target large enterprises, you don’t necessarily have to start with the biggest global companies. “In the very early days, we proved the value serving customers with hundreds of team members, before expanding up into the organisations with tens or hundreds of thousands of employees,” Fabian says.

Startups selling into large companies often struggle to comprehend just how complex their target customers’ businesses are. “We operate in more than sixty countries with a couple of dozen different business units,” says Alexander Pilsl, vice president of procurement at human resources giant Adecco. “So there are a huge number of moving parts in the organisation.”

That scale translates to a massive volume of procurement activity. “We buy a lot of stuff,” says Alexander. “Across technology and other services, annual spend volume is somewhere around €4-5 billion in the average year. Over a typical month, we’ll make a few hundred procurement decisions.”

Each market, and each business unit, may have its own technical and regulatory requirements to fulfil. The role of a procurement function in a large enterprise is to ensure the business has accounted for all potential risks, meeting market expectations through due diligence and request for proposal (RFP) processes. “When we’re buying from tech companies, the technology itself is not the area of biggest concern,” says Alexander. “It’s the security implications for bringing a new piece of tech into the organisation.”

Malicious actors are increasingly focused on finding ways into large enterprises through their supply chains. The risk of weak links in enterprise supply chains has created a large market in itself: vendor risk management is predicted to be a $30 billion market by 2032, indicating just how seriously big businesses treat supply chain security. Alexander’s advice to enterprise-focused startups? “Be prepared for extensive due diligence. You won’t be able to skip the compliance and certification requirements, even if you’re building incredible tech. Security is non-negotiable.”

In a recent interview with Scaling Europe, PolyAI founder Nikola Mrkšić reflected that in the company’s early days, “it felt like we were selling science fiction.” But even in large enterprises, there are often ways in through what Nikola called “extreme early adopters.”

The maze of processes and procedures involved in enterprise sales gives founders a challenge: who is best placed to advocate for your startup internally? ‘Deal champions’ are individuals that are bought in to the potential value early, and can help startups navigate the different stakeholder groups they need onside through the deal process.

But be warned: a passionate deal champion is not a magic bullet that solves all your enterprise procurement challenges. Enterprises have strict rules about how we buy technology products. “We usually need to issue a formal request for proposal (RFP), and we need to evaluate different competitive options as part of the process,” says Alexander.

Global companies always face trade-offs in their buying decision: do you go for the well-recognised, ‘safe’ option, or take more risk and invest in a challenger supplier where the potential upside is higher? As the old saying goes, ‘No-one gets fired for buying IBM.’ Startup and scaleup founders face a tough test: to prove their readiness as a vendor, satisfying many different stakeholders along the way.

Flip’s founders had first-hand experience of the problem they built Flip to solve, having worked at large multinational organisations. But a direct connection to the issue isn’t enough on its own to build trust with very large businesses. So, how to create that bank of evidence to help your potential customer build a compelling business case?

“People used to rely a lot on tools like ROI calculators,” Fabian says. “But enterprise buyers are pretty savvy, and they expect those tools to flatter the data a little. Instead, if you can, spend real time alongside potential customers, watching how their processes work and learning what their problems are.”

The ability to effectively sell into enterprises has many positive-sum effects for founders and their startups. Top talent is eager to work alongside the world’s biggest businesses. And investors appreciate enterprise software’s margins, sticky client relationships and the revenue generated per deal.

But these companies are not easy to break into. Different functions and geographies all have their say in a deal, creating a range of interested parties who need to be brought along with the key stakeholders, such as the internal deal champion. And, of course, the depth, and detail of IT, security, and procurement processes can surprise even seasoned founders.

But the upshot for the founders that break into the enterprise segment is clear: long-lasting, financially rewarding and eye-catching customer relationships that do a lot to bolster credibility and build momentum in the broader tech ecosystem.