"Software buyers see tech sellers as drug dealers. They get you hooked, then hike up the price."

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Dina Kakaras said that on Tuesday night at SFC's portfolio event on selling into corporates. She's spent years on the buying side, in procurement and digital roles at the Ministry of Defence and Worldpay, and it got the biggest reaction of the night.

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I went mostly to listen. Selling into corporates is the challenge I hear about most from founders after a raise, usually because the board pack has a few big logos pencilled in for next year and the team isn't quite sure how to land them.

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What struck me was how much of the evening came back to trust. Nearly every point the panel made was a way of helping a big organisation feel safe choosing a small one.

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Everyone who has to say yes

An enterprise deal has a lot of people in it. The user, the champion, the budget holder, procurement, compliance, IT, finance, legal. The champion who loves your product is rarely the one who signs.

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I understand why teams sell to the champion. They're enthusiastic and they reply to your emails, so it feels like momentum. But if they're your only friend in the building and they leave, the deal usually leaves with them. Aim for more than one named champion per account, and treat losing your second one as an early warning.

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Then work out what each of the others needs to believe before they'll say yes, and what would make them block it.

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That's what we did with Harbr Data, who sell an enterprise data platform. We worked out how enterprise data buyers actually make decisions, built a profile for each person involved and ran campaigns aimed at named decision makers. Marketing got 6x more efficient and pipeline value tripled.

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Will you still be here in 5 years

The person who picks you is putting their own reputation on the line. If you disappear in 18 months, it's their name on the decision.

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So you probably need two versions of your story. Investors want to hear an ambitious start-up. An enterprise CFO wants to hear a stable, credible partner. Both are true, and the trick is choosing which one goes in which room. (Mix them and you end up sounding like a start-up to the CFO and a safe bet to the VC.)

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The panel had a couple of very practical ways to look safer. Take the risk out of the base price: corporate buyers are braced for the hike Dina described, so give them a starting point they can trust. And commit to a date, then hit it. In a long sales cycle, doing exactly what you said you'd do counts for a lot.

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Humara (formerly 15gifts) is a good example. They sell to global telcos, and we moved their positioning from an AI feature to a long-term strategic sales partner, working hand in hand with their sales team. They hit 75% of their annual target for sales-accepted leads in the first month.

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Have the answers before they ask

Go through the deal from each reviewer's side. What will compliance ask for? IT security? Finance? Legal?

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Then have it ready: security and data documents, compliance certificates, a business case with real numbers, contract terms, references. Every missing document adds weeks, and the weeks are where enterprise deals go quiet.

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Make it easy to say yes, too. Show how you fit into the systems they already run, so their team has as little heavy lifting as possible. Plan the training for their staff, including who delivers it and how long before people are actually using it. One panellist suggested saving the customisation for mobilisation, agreeing what can flex during set-up so it doesn't drag out the sale.

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And a nice point from the defence world: the law is fixed, but there's often room to work with policy. Know which one you're up against before you walk away.

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Proof they can find without you

Corporate buyers do a lot of their homework privately. Before they get in touch, they've asked an AI tool who to shortlist, checked social for what people say about you, Googled you by name and only then landed on your website. So visibility is one job across all of those, with proof at the centre.

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That proof can come from a few places. The right logos on the website and in the deck, because buyers look for companies like them. If you don't have those yet, your SMB customers and your founding team's experience can get you in the door. Coverage from others counts too. One founder I know couldn't get enterprise buyers to sign until they'd seen her in 3 named publications.

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Last, be honest about whether you can deliver at their size: team size, support, onboarding, account management. Overpromising wins the deal and loses the renewal.

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The one thing to do this week

Ask your team to take your biggest open enterprise deal and map it on one page. For each person who has to say yes, write down:

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• What they need to believe
• What would make them block it
• What they'll ask for
• Whether we have it today

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Then count how many of them anyone on your side has actually spoken to.

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The gaps in that last column are next quarter's marketing priorities, and they'll usually do more for the deal than another campaign. The founder owns the relationships and the story for each room. The team owns building the material.

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Drop me a line and tell me how many people are on your list, and how many you've spoken to. I'll tell you honestly where I'd start, including when the answer is that you don't need us.

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PS. Thank you to Stephen, Niklas and Ricardo for having me, and to James Owusu, Dina Kakaras, Raoul Lumb and Sam Taylor for such an honest panel. Helping founders sell into enterprise is a big part of what we do at Scale Up: a fractional CMO to set the direction and a senior team to deliver it, from the buyer research to the documents every reviewer needs. Declared interest, obviously. If we're not the right fit, I'll tell you and point you elsewhere.‍