Real-World Scenarios & Access

Who do I actually sell to inside a big company, and how do I find the decision-maker?

A starting point

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 security, legal, and procurement. Start bottom-up with the champion to prove value, then explicitly ask them to walk you to the person who signs, because a champion with no budget is a dead end. Do the org-chart homework before the demo, not after.

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 →

Listen

🎧 Podcast
Free Beginner

Founders: Here's How to Get Your Sales Pitch in Ship-Shape

On First Round Review Podcast (In Depth) by Peter Kazanjy (host: First Round) ~60 min

Why we picked it

A practical, listen-on-a-walk companion to Founding Sales where Kazanjy walks through the actual anatomy of a founder sales call. Perfect for the technical or first-time founder who freezes on the phone and needs a concrete structure.

  • Selling is a learnable skill; practice 'turbo rapport' to get comfortable with strangers
  • Structure a call as rapport, discovery, solution framing, then a clear close for the next step
  • Leading with discovery questions is consistently the most effective approach
  • Get narrow on your ICP first, then expand the motion once it is proven
Open review.firstround.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 →

People also ask

How do I land my first enterprise customer when nobody has heard of us? 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, ... Intermediate 3 resources → 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 → 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 →