ChatGPT turned his product into a commodity at close to $1M ARR. Alon Talmor rebuilt Ask-AI into Mosaic AI, an AI platform for technical support, by narrowing into a market rivals called too hard and selling measurable cost reduction instead of features. The company is now at multiple seven figures in ARR, approaching eight.

Alon breaks down how six months of listening to enterprises produced the product idea, how he closed a $6.5M seed after his co-founder quit in the middle of the round, and how 5-day pilots built on technical support automation turn skeptical enterprise buyers into six-figure customers.

Plus: why he believes the next phase of enterprise AI is agents orchestrating people, not people orchestrating agents.

Alon sold his first startup, BlueTail, to Salesforce, went back for a PhD in AI and question answering, and founded Ask-AI in 2021, a full year before ChatGPT. Today Mosaic AI serves about 100 enterprise customers, with go-to-market in Toronto and R&D in Tel Aviv.

🔑 Key Lessons

• Find a blue pond, not a blue ocean: When funded giants crowd your market, narrow into a segment they cannot serve well. Mosaic left enterprise assistants to own technical support and grew past seven figures.
• Talk to customers six months before investors: Alon pitched no VCs until enterprises had told him their problem. Yotpo's knowledge chaos became the product, and the seed closed on that proof.
• Tell investors bad news before they find it: His co-founder quit mid-raise; he disclosed it immediately and still closed $6.5M. Prettifying reality reads as mistrust, and investors sense it every time.
• Sell the cost reduction, not the feature list: Support is a cost center with a known price tag. Mosaic pitches 50-70% savings on a seven-figure budget instead of arguing about features.
• Pick the metric your buyer cannot argue with: Tickets per engineer per day survived scrutiny where time-to-resolution failed. One customer measured an 80% lift in a week of the pilot.
• Treat build vs buy as your real competitor: With AI coding cheap, enterprises default to building. Win by showing the end state their side project becomes obsolete against, not a feature comparison.

Chapters

• What Mosaic AI does and who it's for
• The real cost of technical support
• BlueTail, Salesforce and the PhD detour
• Founding Ask-AI a year before ChatGPT
• Losing a co-founder in the middle of the seed round
• Radical honesty with investors
• Six months of listening before pitching VCs
• Yotpo and the design partner playbook
• Founder-led sales to the first 25 customers
• ChatGPT turns the product into a commodity
• Agents orchestrating people
• Finding the blue pond: technical support
• Build vs buy: the number one competitor
• The 5-day pilot and the metric that closes deals
• Lightning round

Resources

• Full show notes: https://saasclub.io/498
• Join 5,000+ SaaS founders: https://saasclub.io/email

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

He closed most of the deals himself. It took him ten years to stop. Ross Andrew Paquette bootstrapped Maropost to around $50 million in ARR, and for most of that run he was the discovery call, the demo and the follow-up. It worked well enough to take the business from $300,000 to $27 million in 28 months with six or seven people. Then the thing that built the company became the thing capping it.

Ross breaks down how he won accounts paying $10,000 a month on a five-minute response time rather than features, how two people signed brands like Rolling Stone and Mercedes off a conference floor, and why seven or eight experienced sales leaders all failed at Maropost before he changed what he hired for.

Plus: why he took investor money he did not need, and what it felt like to write a $37 million check three years later to buy it back.

Ross Andrew Paquette is the founder and CEO of Maropost, a commerce and marketing platform with roughly 300 people and 5,000 customers. He started it in 2011 out of his apartment while still selling Oracle ERP software full time, planning on ten customers and a quieter life.

🔑 Key Lessons

• 🤝 Win on service before you can win on product: Ross offered 24-hour live chat and a five-minute reply when Maropost had ten or fifteen customers, and landed accounts paying $10,000 a month without the deepest feature set.
• 🎯 Sell to people who already trust you: Three or four customers from Ross's previous jobs signed almost immediately, which is why Maropost had real revenue before it had a finished product or any marketing spend.
• ⚡ Founder demos beat decks: Ross ran simple discovery then a personalized demo with no slides, and credits his edge to having designed the features himself rather than to any sales methodology.
• 🚀 Concentrate spend where your buyers already are: Buying top-tier sponsorships at a handful of conferences let two people sign brands like Rolling Stone and Mercedes off the floor, helping take Maropost from $300,000 to $27 million.
• 🧠 Hire for tenacity, not logos: Seven or eight sales leaders with strong resumes failed at Maropost because their experience came from different engines, price points and company sizes that did not transfer.
• 💰 Capital you do not need still costs you: The 2016 secondary brought expectations rather than money Maropost required, and growth fell from around 400 percent to 6 to 10 percent before Ross bought the investors out.
• 📉 Getting out of founder-led sales takes longer than you think: Ross spent about ten years moving from what he called "Ross and Co" to an actual organization, and says it was the hardest part of building the company.

Chapters

• What Maropost does and who it serves
• The ten-customer lifestyle plan
• Getting the first customers from old relationships
• The developer who kept disappearing
• His mother's advice and the oDesk hire
• Charging $10,000 a month with a small product
• Why most founders cannot sell
• From $300K to $27M in 28 months
• Why seven or eight sales leaders failed
• Writing the $37 million check

Resources

• Full show notes: https://saasclub.io/496
• Join 5,000+ SaaS founders: https://saasclub.io/email