Startup sales — founder-led done right

Three phases. Each one has a job.

1. Qualification (first 10 min) — establish whether they have the problem, the budget, the timeline, and the authority. The mistake: skipping straight to demo. "What made you book this?" + "What are you doing today to solve [problem]?" + "Who else is involved in deciding?" + "What's your timeline?"

2. Discovery + demo (20-30 min) — show ONLY what's relevant to what they told you. A demo that shows 12 features when they have one problem is a tell that you don't listen. Best founders demo three screens, max, in this segment.

3. Close (last 10 min) — "Based on what we've talked about, does this solve your problem?" Pause. Then: "What would need to be true for you to move forward in the next two weeks?" Don't fill silences. Get specific commitments.

After every call: write down what they said in their own language. Within 50 calls, you'll have the marketing copy.

Click-through ToS — appropriate for self-serve under ~$500/mo. Stripe Checkout + a ToS link covers most things. Don't over-engineer.

Order form on top of a Master Service Agreement (MSA) — appropriate for B2B sales above ~$1k/mo. MSA covers terms once; order form covers each deal (scope, price, term, start date).

Custom contract — only when the customer requires it. They will. Have your lawyer prepare a 1-page "position document" of which clauses you'll fight on (data ownership, liability cap, IP, exclusivity) and which you'll concede on. Saves $5k of legal back-and-forth per deal.

Common gotchas:

• Auto-renewal vs annual term — you want auto-renewal; enterprise customers often want notice periods
• Liability caps — start at 1× annual contract value; resist unlimited liability
• Data residency — enterprise customers in EU/UK will require it; check before promising
• MFN clauses — "if you give anyone else a better price, we get it too" — say no; concedes too much pricing power

Trip-wires for hiring the first account executive:

1. The founder is doing >25 sales calls/week consistently
2. Win rate from qualified call to close is reliably ≥30%
3. ACV is high enough to cover an AE's OTE (Base + Variable target) with ≤5 closed deals/quarter
4. Sales conversations are running on consistent positioning + qualification

If you hire before all four, you'll spend 6 months coaching them to do what you do — without the message dialled.

When you do hire:

• Profile: 3-5 years AE experience at a similar-stage company, ideally with the same kind of buyer
• Comp: 50/50 base/variable; OTE of $120-180k at seed/Series A in US (lower in other markets)
• Ramp: 3 months at 50% quota; full quota by month 4-6
• Founder still selling: the founder must close the biggest deals for the first 12 months even after hiring the AE