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Selling to enterprises (B2B)

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How long is a B2B sales cycle and how do I not run out of money waiting? Enterprise cycles routinely run 3 to 9 months (longer with security and procurement), so assume every deal takes twice as long as the champion prom... Intermediate 3 resources → They want a free pilot, should I do it? Free pilots attract tire-kickers and give you no signal on real buying intent, so default to a paid pilot, even a small refundable one, to force th... Intermediate 3 resources → How do I survive procurement, legal, and security reviews as a tiny startup? Procurement, legal, and security exist to slow you down, so prepare the paperwork before they ask: a standard MSA, a security one-pager, a data-han... Advanced 3 resources → How do I price my very first enterprise deal without leaving money on the table or scaring them off? Price against the value of the problem you solve, not your costs, and anchor high enough that the buyer takes you seriously as a real vendor rather... Advanced 3 resources → Should I hire a salesperson yet, or keep selling founder-led until I hit a certain revenue? Keep selling founder-led until you've closed roughly your first 10 enterprise deals yourself and can write down a repeatable playbook, because a sa... Intermediate 3 resources → A big company wants to acquire us instead of buying our product. How do I even think about this? Treat an early acquisition offer as a signal that you're onto something, not as an exit to grab out of relief. Most first offers are acqui-hires dr... Advanced 3 resources → How do I negotiate multi-year contracts, discounts, and renewal terms without training customers to always squeeze me? Never give a discount for free: trade it for something you want, like a longer term, an upfront annual payment, a case study, or a reference. Hold ... Advanced 3 resources → When should I move from selling one deal at a time to building a repeatable, scalable sales motion? Systematize only after founder-led selling has proven the same pitch, buyer, and objections win repeatedly, because scaling an unproven motion just... Advanced 3 resources →
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