Founder-Led Sales: He Learned to Sell and Closed 50 Customers

He walked into his first pricing call asking for $100,000 and walked out with $10,000 a year. Shahar Azulay had never sold anything before co-founding groundcover, and the product he was selling had no user interface yet, just a sensor and some dashboards. He took it anyway, and still argues that was the right call. Shahar explains why founders should close their first dozen customers at almost any price, how he published a per-host list price and then discounted it up to 70 percent, and how his first 50 to 100 customers came from his own network plus 10 to 15 LinkedIn messages a day. Plus: the moment customers started ripping Datadog out on their own, before groundcover had built anything to help them do it. Shahar Azulay is the co-founder and CEO of groundcover, an eBPF observability platform that lets engineering teams monitor production without changing their code. He has grown it to eight-figure ARR with more than 250 customers, competing head-on with Datadog and New Relic. 🔑 Key Lessons Close your first dozen deals at any price: Early contract value teaches you nothing. The reps, the reference logos, and learning to survive security and legal reviews are what make the next twenty deals closeable. Publish your price when you sell to mid-market: A public number per host anchors the conversation and skips a negotiation a first-time founder will lose. groundcover listed $30 per host, then discounted up to 70 percent. Don't expect to grow your earliest accounts: Shahar never planned to 10x those first contracts. Chasing them traps you in old relationships when the rest of the market is still unsold and will pay more. Your first sales calls are really feedback calls: Prospects treat a founder as someone to advise, not buy from. Shahar framed early meetings as "we'd love to show you what we're building" and converted from there. Selling the deal is not replacing the incumbent: groundcover closed customers who still kept Datadog running. The post-sale migration motion only got built after those early displacement attempts visibly failed. A remote first hire with no local team will fail: The first SDR in North America was hired alone, remote, under marketing, with no one around him. Shahar calls it a failure of gravity, not of the person. Bet on the technology your team can already build: eBPF worked for groundcover because the founders came from cybersecurity and knew how to ship a safe kernel agent. Incumbents selling SDKs still struggle to copy it. Chapters Introduction What groundcover does and who buys it Why observability pricing stopped making sense Bring your own cloud and charging per host From Apple and cybersecurity to founding groundcover Discovering eBPF and betting the company on it Why no other observability vendor was using eBPF The first customer, three months in Asking $100K and closing at $10K Why founders should close at any price Publishing list pricing and discounting 70% Being the entire sales function Prospecting on LinkedIn, 10 to 15 a day Getting out of the friend zone on sales calls Hiring the first AEs, SDRs and sales engineers When customers decided it could replace Datadog Failing to rip out the incumbent Learning when you have no leverage Lightning round Resources Full show notes: https://saasclub.io/497 Join 5,000+ SaaS founders: https://saasclub.io/email