Real-World Scenarios & Access

How do I land my first enterprise customer when nobody has heard of us?

A starting point

You don't win the first logo with a brand, you win it with a relationship and a sharply-scoped problem you can prove you solve. Mine your network, your investors, and your advisors for a warm intro to one specific team that is on fire about the exact thing you fix, then over-deliver until they become your reference. Your first enterprise customer is bought on trust and founder credibility, not on your homepage.

Go deeper

Watch

▶️ Video
Free Beginner

Enterprise Sales for Founders

On Y Combinator Startup School by Pete Koomen ~35 min

Why we picked it

Pete Koomen took Optimizely from zero to $100M+ ARR, and here he breaks the enterprise funnel down for exactly the person who finds it terrifying: the technical founder who has never sold. It is the clearest short primer we know on how a builder starts closing real deals.

  • Founders can and should run enterprise sales themselves early, treating each deal as a source of product feedback
  • Map the funnel stage by stage and know which stakeholder you need at each one
  • Identify a real champion inside the account and use them to reach the economic buyer
  • A repeatable, learnable process beats charisma when selling complex software
Open ycombinator.com →

Read

📖 Book
Freemium Intermediate

Founding Sales: The Early Stage Go-to-Market Handbook

From foundingsales.com by Peter Kazanjy book (~400 pages)

Why we picked it

The authoritative handbook on founder-led sales, written for technical/first-time sellers building B2B SaaS. Readable free online via membership, and covers the whole motion end to end.

  • Do ~50 demos and hit a ~20%+ win rate before hiring your first sales rep.
  • Discovery before demo, understand the problem before you pitch.
  • Dedicated chapters on prospect outreach and demo appointment setting.
  • Turn founder selling into a documented, repeatable, transferable process.
Open foundingsales.com →
📄 Article
Freemium Intermediate

How to win your first 10 B2B customers

From Lenny's Newsletter by Lenny Rachitsky ~15 min read

Why we picked it

A tactical follow-on covering the channels and motions top B2B startups scale after the first ten. Grounds distribution strategy in real company examples.

  • Content/SEO is a surprisingly dominant B2B channel (Vanta, Amplitude, Figma, HubSpot).
  • The core B2B channels: self-serve inbound, sales-assist inbound, outbound, content, paid, partnerships.
  • Pick and systematize the one channel that compounds for you.
  • Distribution strategy should follow evidence, not fashion.
Open lennysnewsletter.com →

People also ask

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 → Who do I actually sell to inside a big company, and how do I find the decision-maker? Big companies have three roles you must map: the champion who feels the pain daily, the economic buyer who controls budget, and the blockers in sec... 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 → Should I use design partners, and how do I structure the deal? Design partners are your cheat code to product-market fit: a handful of committed early customers who co-build with you in exchange for influence, ... 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 →