He had never sold anything, and his first customer talked him down from $100,000 to $10,000. Shahar Azulay is the co-founder and CEO of groundcover, an eBPF observability platform that lets engineering teams monitor production without touching their code. He has grown it to eight-figure ARR with more than 250 customers, going up against Datadog and New Relic. Three months into the company, groundcover closed its first customer through a connection to a head of DevOps. There was no user interface yet, just a sensor and some dashboards in Grafana. Shahar went into the pricing call asking for $100,000 and came out with $10,000 a year, because neither founder knew what they were negotiating against. His first 50 to 100 customers came from his own network and 10 to 15 LinkedIn messages a day, and it took roughly 50 customers to reach the first $1M in ARR. Stay for 36:55 where Shahar reveals that his customers decided groundcover could replace Datadog before he believed it himself, and that the first few attempts to rip out the incumbent failed. š KEY LESSONS š¤ 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. š° 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. š§ 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. š¤ Your first sales calls are really feedback calls: Prospects treat a founder as someone to advise, not buy from. Shahar framed early meetings as a chance to show what they were building and converted from there. š¢ 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. š 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. š ļø 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. ā±ļø TIMESTAMPS 00:00 Introduction 01:41 What groundcover does and who buys it 02:28 Why observability pricing stopped making sense 05:23 Bring your own cloud and charging per host 06:39 From Apple and cybersecurity to founding groundcover 09:01 Discovering eBPF and betting the company on it 10:48 Why no other observability vendor was using eBPF 16:10 The first customer, three months in 17:47 Asking $100K and closing at $10K 20:54 Why founders should close at any price 22:13 Publishing list pricing and discounting 70% 24:39 Being the entire sales function 26:59 Hiring the first AEs, SDRs and sales engineers 32:11 Prospecting on LinkedIn, 10 to 15 a day 34:44 Getting out of the friend zone on sales calls 36:55 When customers decided it could replace Datadog 43:32 Failing to rip out the incumbent 45:52 Learning when you have no leverage 47:18 Lightning round š§ Full Show Notes: https://saasclub.io/497 š Get weekly 5-minute SaaS insights: https://saasclub.io/email #SaaS #FounderLedSales #SaaSPricing