Sure there is pain, but 5,000 seats all at once is usually worth it. The thing to avoid like the plague is RFPs. They will kill your startup faster than anything. Your customers should be early adopters and early markets do not do RFPs.
Why it a death sentence to sell to organizations with RFPS
Is it cause of other people putting bids? What if I want to sell to government agencies as a bootstrapped business
Thanks so much
Big picture: it just frames things the wrong way — if they want to buy from you, then they're buying from YOU. If you get pulled into an RFP, then you're selling to THEM.
That doesn't mean RFPs are always bad, just that they can be terrible for startups that are too small, and not prepared for the process.