one of the best sales advice we picked up during YC is the "McKinsey Model" a lot of deals at early-stage startups die for the same reason: your champion is afraid to advocate for your product if they push for it internally and it doesn't work out, their job is on the line so they never come back to you and hit you with the "we need to align internally first" that's why you need to be their McKinsey consultant: instead of them pitching, you personally take the blame after every demo, send them: - a one-pager - a security doc - an ROI calculator with their numbers - useful context/overview of your industry that can help with what they're struggling with right now - a pre-written slack message they can forward make it as easy as possible for your champion to forward your material without them feeling responsible for integrating your solution or "fighting" for it

We hired an ex-salesforce Account Executive to learn how they close 6 figure contracts: Unlimited client dinner budgets. One of our new team members (ex-salesforce AE) would basically email "Lunch on me?" to his prospects. This was his "foot in the door" moment. After that it was game on. Your goal in the free lunch: 1) figure out who is important in the buying process 2) get a way in to these people for a second free lunch or dinner After that, it’s just a cascading waterfall of meet ups at their favorite places. People don’t say no to this. You keep meeting with more and more people until the deal closes. Startups with a high enough ACV should think about adopting this more, especially when trying to move into mid-market/enterprise.

one of the best sales advice we got back in YC was the "ikea effect": if you are in the middle of a demo, never just open your laptop and show a generic feature dump. before you show anything, ask this: "if you were in my shoes, what would this platform need to show you to prove it can solve your problem?" the prospect will give you a checklist of 2-3 things. start by showing exactly those 3 things. people love what they build themselves. when they define the criteria for success, they can't argue when you deliver it

the amount of gifts you receive just by working at a Fortune 500 company is insane you have no idea how intense the competition is. some companies are spending millions on sales gifts to close enterprise customers: 1) Salesloft AE sent a LEGO set after seeing a Star Wars poster in a prospect's Zoom background (Closed a $250k deal) 2) Chili Piper sent an automated $5 coffee voucher 1 hour before a demo with the note: "Coffee is on us for the call" (Increased meeting show rates by 33%) 3) another company sent Pizza to a prospect’s Technical Support department after solving a recent outage to get a demo with an IT Director who was ignoring them (Director called back in 20 mins) 3) Gong sent Pink Unicorn Piñatas to Fortune 500 CFOs with a note: "Sales is like a piñata - the value is hidden inside" (Influenced $33M in pipeline) 4) another one automated Champagne delivery the moment a past "Champion" (someone who used their tool at a previous job) starts a new role at a target account 6) SDRs research a prospect's Alma Mater (College) and send a custom mug with their college logo and a gift card for a "Sunday Lunch" 7) SentinelOne sent "James Bond" Aston Martin LEGO sets to Cybersecurity C-levels because they are official F1 partners and targeted Gen X nostalgia (38.7x ROI) 8) another Company sent custom View-Masters (the 90s toy) with slides showing the prospect’s current "broken" workflow vs. the "fixed" version 9) AEs send Live Bamboo Plants to prospects with a note: "Looking forward to watching our partnership grow" (Stays on the desk for months as a permanent ad) 10) Terminus sends "Backyard Fire Pit" kits to high-value prospects to "warm up" cold accounts during the winter months (Resulted in a 7-figure pipeline)

during YC, we learned about a sales tactic called "internal timeline closing" that helped us hit every single one of our 2-week sales goals: we would say something like this: “just to be transparent, we’re trying to hit our Q1 revenue goals right now, so we might have some flexibility on pricing. is that something that would make sense in your world, or would timing not really matter here?” as a startup you are constantly trying to hit internal numbers to keep momentum. that same context can help you close prospects who are interested but are still undecided

one of the most underrated sales strategies we learned during YC is "rejecting prospects" this is what we tell prospects when it’s not a fit: “here’s what we’re great at today. here’s what we don’t do. and here’s what will be possible in the next 6 months” many founders and sales reps are afraid to lose deals so they oversell “coming soon” features we tried the opposite and even recommended competitors early on when we knew we were not the right fit. it sounds counterintuitive, but many of our inbound leads now come from referrals, often from people we previously turned away you just need to make sure to reject prospects the right way. be extremely clear about what you are great at and what you are not. fire bad fits, they push the wrong features, overload support, and churn anyway. protect your ICP

This is what YC taught us about how to get your first paying users: 1) founders MUST do sales: You can't outsource early sales or hire a sales team immediately. You need to do it personally to understand the customer's problem because the product will initially be bad, only a founder's passion can sell a work-in-progress. 2) Manually recruit customers and do things that don't scale. Brex founders signed up their first 10 customers from their YC batch. 3) Simple cold emails: Use plain text, no fancy formatting/HTML, and keep it very short (max 6-8 sentences). Include social proof, avoid jargon and have a clear call to action for a demo or call. 4) Work Backwards from Your Goal: If you need 2 customers, you can’t just reach out to 10 people. You likely need to send 500 emails to get 250 opens, 20 replies, 10 demos, and finally 2 customers. 5) Most people will ignore you and that is fine. Outbound sales is a numbers game designed to sift through the majority to find the specific "early adopters" who are willing to take a risk on a new product. 6) Start with the Easiest Targets: Do not try to sell to big enterprise companies with bureaucracy initially. Sell to startups (short decision lines), people in your network, or previous colleagues. Pick the "low-hanging fruit." 7) Fire Bad Leads Quickly: If a prospect is dragging you along for multiple calls without committing, or if they don't have the budget, let them go immediately. Focus your limited time only on those likely to close. 8 ) Charge Immediately (No Free Trials): For B2B, if they don't pay, they aren't a customer. Avoid free trials and instead, offer a money-back guarantee or a monthly opt-out clause. Pricing validates that you are solving a real problem. almost every single company in YC gets real revenue. It's very hard, but avoid the temptation to give away your product for "feedback." 9) Track Data in a CRM: Do not guess if sales are working. Use data providers like CrustData or Apollo to get leads and to track your conversion rates at every stage. If you have 0 customers, data will tell you if the problem is the email subject line (open rate) or your pitch (demo-to-close rate). 10) Don't Forget Manual Onboarding: Closing the deal isn't the end. You need to manually onboard early customers to ensure they actually use the product. If you skip this, early churn will be high because early products are hard to figure out.

Vercel already replaced their 10-person inbound SDR team with 1 GTM Engineer if you still don't know what GTM Engineering is and how it will change your sales org: 1) install Claude Code 2) get a free Crustdata test API key 3) describe every workflow you're currently doing that isn't directly adding revenue (researching, building lists, enriching...) 4) ask Claude Code how to automate everything you just described using the API + any other tools in your stack

Every time I'm at a YC event, I get asked how to do GTM. My answer is always the same - here are the bullet points: 1. build your lead lists, use tools like Crustdata or Apollo 2. don't use AI to create the outbound email - make it as concise as possible 3. take a look at deliverability metrics - iterate email every day - make it more and more punchy 4. separately, use LI Sales Nav to write 2 sentence outreach to people - preferably with warm connection (common university, etc) 5. Post on LinkedIn everyday 6. invest in SEO spend 80% of your time on the above and you will breakthrough and get demos Every founder who followed this advice with enough discipline saw results.

i don’t think people are taking this seriously enough one of our AEs just got off a demo with a prospect who is building internal sales/GTM workflows with Replit to replace a SaaS tool they are currently paying for, the Replit agent told him to use our APIs, so he reached out he showed us a demo of one of the apps he built: 1) pull a list of everyone who attended a specific event 2) enrich each person, run web search on people with only a username 3) filter the list down to their ICP 4) rank prospects by buyer intent and priority he was non-technical seeing this trend more and more over the last ~2 months. looks like GTM teams at startups and enterprises will be one of the biggest growth channels for vibe coding tools

YC taught us to never take a sales meeting without asking these 7 questions first: 1) What made you decide to take this call 2) Tell me about the problem. How long have you had it 3) How bad is it? Who else does it affect? 4) How do you quantify the cost/impact of this problem 5) Why haven't you solved it already? 6) What is your budget for solving this? 7) How does your organization buy software? Who makes the decision?

We just hit $4M ARR. This was the hardest $1M marker we've reached so far. 5 key lessons learned from this journey: 1) Prioritize recruiting - Our team is spread thin now due to hiring slowly. So, spending more time on recruiting great engineers and GTM talent. 2) Be proactive with current customers - We are just over a year into launch and now have to deal with churn. So we need to ensure customer happiness and awareness of new products. 3) Build faster - We know what customers want, focusing on that will reduce churn and increase satisfaction. 4) Keep focus on top of funnel - We have 5-6 sources of leads. The goal now is to get better leads rather than more leads. 5) Never slow down when you have momentum - It seemed like there was less urgency due to July/August malaise. This cannot happen again. Momentum is very important for a startup.

a simple sales template someone sent me during YC that helped us close more customers was updating our CRM like this after every call: "the prospect is struggling with [problem] because of [root cause], which is costing them [specific impact]. if this isn’t fixed by [date], [consequence] will happen"

we just renegotiated our Slack Enterprise upgrade with Salesforce instantly understood how Salesforce is valued at $150B after that call their AE used the exact same tactics every enterprise sales org uses: 1) "our quarter ends Friday, so I can get you a bigger discount if you sign by then" and kept pushing: "if I send over the proposal today, would you be able to sign by Friday?" 2) gave us two pricing options where the bulk purchase was designed to look like the obvious choice 3) used our own growth number against us, "you're adding X users/month, so you'll need these seats anyway. why not lock in a better price now?"