Sammeli Sammalkorpi has spent more than two decades selling enterprise software to some of the largest companies in the world. And after listening to his session at SaaSiest, one thing became very clear:
“Enterprise sales is not a process. It is controlled chaos.”
The Reality of Enterprise Sales
The CEO and co-founder of Sievo has built one of the world’s leading procurement analytics companies, serving global enterprises with an average contract value of around €190K. His customers include some of the largest organizations on the planet, and according to Sammeli, Sievo now sees purchase transaction data equivalent to roughly 2% of global GDP every year.
But despite the scale, sophistication, and years of experience, Sammeli described enterprise sales in the simplest possible way:
“A whack-a-mole game.”
You think the deal is done, then a new stakeholder appears. Legal raises concerns. IT rejects the architecture. Procurement introduces a new process. Security blocks access to data. Every time you solve one issue, another one appears. And that is exactly why so many SaaS companies underestimate enterprise sales.
Founders often imagine enterprise deals as a linear funnel. Problem identification. Vendor evaluation. Selection. Signature. Reality looks nothing like that.
Most of the important conversations are happening when you are not in the room. Internal politics. Budget discussions. Executive concerns. Team resistance. Risk management. The “meeting before the meeting,” as Sammeli called it. That means the real job in enterprise sales is not simply pitching your product. It is navigating organizations.
Stakeholder Mapping Is Everything
One of the strongest takeaways from the session was Sammeli’s obsession with stakeholder mapping. He showed a real example of how Sievo maps relationships inside enterprise accounts, identifying who influences whom, where reporting lines exist, what each stakeholder cares about, and where resistance may emerge. And then comes the most important piece: finding internal coaches. Not champions but coaches. People inside the customer organization who genuinely want you to win and are willing to tell you what is really happening behind closed doors. Without those relationships, enterprise sales become guesswork.
“Enterprise Sales Is Not About Measurement”
Another refreshing part of Sammeli’s talk was his honesty about metrics. Coming from the CEO of an analytics company, most people expected a deep discussion around attribution models, conversion funnels, and forecasting precision. Instead, he said something most SaaS leaders probably need to hear:
“Enterprise sales is not about measurement. It’s about judgment.”
Why?
Because enterprise sales are a low-signal environment. When you close a small number of large deals every year, sample sizes are tiny. Sales cycles are long. Attribution is messy. A single deal can involve hundreds of interactions over multiple years. One customer Sievo recently closed had their first interaction with the company twelve years ago. How do you accurately attribute that journey?
Sammeli’s view is that most SaaS companies overcomplicate enterprise measurement. The one thing that actually matters is understanding which channels create pipeline consistently over time. Not leads. Not clicks. Not short-term attribution games. Pipeline is what matters. And you need to evaluate it patiently, often annually rather than monthly, because enterprise sales simply move too slowly for rapid optimization cycles.
Why Enterprise Reps Fail in Startups
But maybe the most valuable part of the session was his brutally honest story about scaling enterprise sales teams. Like many technical founders, Sammeli believed that hiring experienced enterprise salespeople would unlock growth. So Sievo hired proven commercial talent from larger software companies across Sweden, Germany, and France.
Some were incredibly talented. Several still failed completely. One salesperson sold nothing in twelve months. Another sold zero deals in fourteen months. One successfully sold products the company did not even have yet.
The problem was not the salespeople. The problem was the missing infrastructure around them.
Large-company enterprise reps are used to operating with pre-sales support, legal teams, product marketing, security specialists, customer references, and mature internal systems. Early-stage SaaS companies rarely have any of that. So when founders expect experienced enterprise reps to magically scale sales without support structures, disappointment usually follows. Sammeli explained that before enterprise sales become scalable, founders themselves often need to build the infrastructure manually. Only later can experienced sales operators truly thrive.
Industry Matters More Than Geography
Another myth Sammeli challenged was the obsession with geographic expansion.
Many SaaS leaders believe selling into Germany, France, the Nordics, or the US requires completely different approaches because “the markets are different.”
Sammeli disagrees.
In enterprise sales, industry matters far more than geography.
A manufacturing company in Germany often behaves more similarly to a manufacturing company in the US than to a bank located in the same city. Large enterprises share operating models, governance structures, procurement processes, and stakeholder dynamics regardless of headquarters location. The real complexity lies in understanding individual people and organizational incentives, not national stereotypes.
Play the Long Game
And then came perhaps the most important lesson of the entire talk:
Play the long game.
Too many SaaS companies think about enterprise sales as closing deals.
Sammeli thinks about building decades of trust. Every interaction matters because people move between companies. A stakeholder who trusted you five years ago may become your internal sponsor at their next employer. Over time, those relationships compound. Today, when Sievo enters many enterprise sales cycles, they already know multiple people inside the organization who can help them navigate the account. That is fifteen years of relationship-building.
In a SaaS industry obsessed with speed, automation, and growth hacks, Sammeli’s message was almost countercultural.
Enterprise sales still come down to people. Not flashy tactics. Not perfect attribution models. Not aggressive automation.
It comes down to trust. And the companies that understand that tend to win the biggest deals.
