You land a pilot with a major Big Tech company. Big logo. Big potential. Big headache.
At first, it’s all smooth: great meetings, strong internal champion, alignment on value. But then procurement enters the chat—and everything slows to a crawl.
Security reviews that want your SOC 2 and your server room floorplan. Legal clauses written for multinationals. Net-90 payment terms like you’re their outsourced cashflow solution.
Meanwhile, your roadmap—what actually got you this far—starts grinding to a halt. Engineers pulled into audits. Product managers explaining features to procurement people who’ve never used software.
One week turns into eight, and you’re wondering if the logo’s worth the burn.
This happens more than founders admit. And most dig in too late.
Here’s how to play it differently—before your sprint board turns into a legal inbox:
Set the tone early. When procurement gets looped in, state the obvious: “We’re a startup. We’ll meet real compliance needs, but we can’t spend two quarters in contract limbo.” Buyers respect clarity more than silence.
Protect your team. Assign one commercial owner to the deal—someone who can handle back-and-forth and only escalate to engineering when absolutely necessary. Keep product focused on product.
Push back politely. A lot of contract language is boilerplate. Flag it. Ask what’s essential. You’ll be surprised how fast “non-negotiables” become optional with the right framing.
Lock in cash terms. Don’t accept net-90 unless you’re pricing for it. Try milestone billing or partial upfront. You’re not their bank.
Know your walk-away point. If the deal’s bleeding time, money, and attention, it might not be a win—even with the logo.
Big logos can be transformational. But only if you close them without pausing your company to do it.
Negotiate like your roadmap depends on it—because it does.
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