We were chasing a six-figure deal in the enterprise space. A well-known client. The sale felt like a marathon—demo, security review, procurement, legal..
And then came the kicker: net-60 plus end-of-month payment terms, biannually.
By the time the cash landed, it was often a full year after the first discovery call. Meanwhile, payroll, cloud bills, and contractor invoices didn’t wait.
Sound familiar?
Long sales cycles aren’t just a strategy risk—they’re a cash flow trap. And the fix isn’t just closing faster. It’s getting paid smarter.
Here’s what worked.
We started writing payment terms into the proposal, not the final MSA. Not every client accepted it, but the ones who did saved us from borrowing to stay alive.
For compliance-heavy buyers, we framed it as a commitment mechanism: if we’re locking the roadmap around your use case, we need some skin in the game.
And for the stubborn ones? We offered small prepayment incentives—2–3% off if paid upfront. Cheaper than debt.
The key is this: don’t wait until the redline phase to talk terms. By then, you’re negotiating from a weaker position.
Lead with it. Set the frame early.
Because in startup land, margin matters—but timing matters more.
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