Pilots and closing

Demo their workflow, not your feature tour. Agenda: confirm pain → show the three screens that kill that pain → discuss next steps. Record objections. Timebox.

Pilots that do not become zombies

Free open-ended pilots are where deals go to die. Prefer:

• Paid pilots or short contracts with opt-out
• Written success metrics (e.g. "resolve ≥15% of tier-1 tickets on a 1,000-ticket sample")
• A calendar decision date and named economic buyer

A POC should prove the value equation your champion will take to the CFO — not provide free consulting forever.

Closing and price

Ask for the order. "What would need to be true for you to sign this month?" beats another feature build. On price: know your floor (gross margin, CAC payback, precedent). Trade term (annual prepay, multi-year, reference rights, case study) for discount rather than naked price cuts. Multi-year logos help ARR optics and cash. Deep discounts train the market to wait.

If proposal→won is 5%, the issue is often pricing, security blockers, or non-ICP — not prettier slides. Rough early rates (measure yours): discovery→demo 50–70%, demo→proposal 40–60%, proposal→won 20–40%.

If you are the technical cofounder, own solutions-engineering for pilots: data connectors, eval harnesses, success dashboards. That skill set often becomes the first SE hire's job description.

When sales asks for a feature to close one deal, ask whether it matches ICP and NRR — or is a one-off tax.

Common mistakes

• Open-ended free POCs with no metric and no date.
• Naked 40% discounts instead of trading term.
• Building one-off features to close a non-ICP logo.

Check yourself

1. What three things turn a POC into a decision? Paid or bounded, written success metrics, and a named buyer with a date.
2. Buyer says "too expensive." What do you trade instead of list price? Term — annual prepay, multi-year, references — against a smaller discount.

Key takeaways

• Demo their workflow. Timebox. Record objections.
• Paid, metric-bound pilots with a decision date.
• Ask for the order. Trade term for discount.
• Proposal→won at 5% is pricing, security or ICP — not slides.

Further learning

When the motion repeats: first sales hires.