The SaaS Podcast: How B2B SaaS & AI Founders Get Customers

A Fortune 100 retailer put out an RFP for an ad server and didn't like any of the answers. Then they found AdButler online. Rajiv Khaneja had never sold to an enterprise, and AdButler had 12 people. He showed up at the retailer with a laptop and a demo, and signed his first Fortune 100 customer.

Rajiv explains how AdButler sells enterprise deals with no salespeople: inbound leads from a contact form, product-led demos, missing features built in weeks, and month-to-month contracts instead of lock-in. He also shares the pricing mistake he made for 15 years.

Plus: why he thinks AI will kill the settings page and give every customer their own version of your software.

Rajiv started AdButler as a teenager after DoubleClick hung up on him. It ran as a side project for a decade, with plans from $9.95 a month, before he went all in and built it into a $10M SaaS.

🔑 Key Lessons

Let the demo be your sales process: AdButler has no salespeople. Product people show the software screen by screen, and Rajiv watches the room to see what excites buyers. That demo won the retailer and AdButler's next enterprise deals.

Answer the gap before the buyer asks: At the end of every demo, AdButler shows how it will fill whatever is missing. Promising three weeks against a competitor's six months, then shipping in two, won long-term enterprise contracts.

Price on value, not on your costs: For 15 years, Rajiv charged a multiple of what it cost to serve an ad. His first enterprise deal was many orders of magnitude bigger than his SMB plans.

Don't lock customers in with contracts: AdButler offers enterprise clients month-to-month terms and signs longer ones only when asked. If a contract is the only thing keeping a customer, Rajiv says you've already lost them.

Put an enterprise door on your website: After that first deal, AdButler added an enterprise tier with a contact form. Its first 10 enterprise customers all came through inbound leads, with no outbound sales team at all.

Split features into one-person pieces: AdButler breaks every big feature into the smallest units one engineer can ship alone, like single API endpoints. Fewer people syncing means fewer meetings and much faster custom builds.

Treat AI like the tractor next door: Rajiv tells his team the farmer with a tractor sells carrots cheaper than the one with an ox. Founders who won't adopt AI will get priced out the same way.

Chapters

What AdButler does and the size of the business

How AdButler differs from Google Ad Manager

A polls website and the call to DoubleClick at 14

Building his own ad server

Close to seven figures before finishing high school

Turning down a $2.5 million acquisition offer

The dot-com crash and the pivot to paid software

10 years as a side project at $9.95 a month

Going all in on AdButler

A Fortune 100 retailer's email and the 29-tab RFP

A laptop demo for a room of 25

Enterprise customers 2 through 10

Building custom features in weeks, not months

Why AdButler offers month-to-month contracts

Shared Slack channels and one-engineer features

Why AI makes configurable software obsolete

Lightning round

Resources

Full show notes: https://saasclub.io/500

Join 5,000+ SaaS founders: https://saasclub.io/email

He asked buyers to rip out their whole Salesforce stack. The first 200 to 300 called him crazy. David Zhu, co-founder and CEO of Reevo, built an all-in-one AI sales platform and learned the hard way how to sell it. He kept the platform and changed the ask: buyers start with one piece, like the dialer, the sequencer or the AI-native CRM.

David explains why Reevo spent two years in stealth before selling, how a founder he met at an AWS program became the first paying customer before seeing the product, and how Reevo got to $1M ARR in 6 months while an introvert ran founder-led sales. He also shares the Mom Test mistake he made early on.

Plus: why the startups that happily adopted his whole platform turned out to be false validation.

David ran engineering teams at DoorDash and worked with Keith Rabois at OpenStore before founding Reevo, his fifth startup, with a founding team of 14. Reevo now serves hundreds of customers without paid marketing.

🔑 Key Lessons

Be strict on architecture, flexible on the sale: Reevo kept its all-in-one platform but stopped demanding rip-and-replace. Letting a buyer start with one tool asks for a much smaller first yes than throwing out Salesforce.

Give buyers three doors, not the whole menu: Reevo groups its land motions into pipeline generation, deal progression and manager reporting. Prospects pick their biggest pain instead of facing every module and integration at once.

Watch out for false validation: Startups with no RevOps leader or security review adopted Reevo's whole platform easily. That said little about the entrenched mid-market buyers Reevo actually wanted to win.

Play to your strength, not someone else's game: David had no sales brand, so he built on what he did have, a dense engineering team. Copying founders who have distribution you lack is how you lose.

Open the deal, then hand off the close: David, an introvert, sent the first email and ran the intro call. A founding sales leader from HubSpot closed, and Reevo copied his talk tracks across 12 to 15 AEs.

Ask for payment to test your discovery: Early prospects praised David's pitch, then said no when he asked them to pay. The Mom Test's non-leading questions get you to the honest answer sooner.

Don't outsource ICP discovery: Paying a vendor $50,000 to run your outbound skips the learning. David says founders without product-market fit have to do discovery themselves or risk a false start.

Chapters

What Reevo does and who it's for

Founding team of 14 and the size of the business

From DoorDash and OpenStore to the idea for Reevo

Why Reevo built in stealth for two years

The first paying customer from an AWS program

The Mom Test mistake and winning without a sales brand

Founder-led sales as an introvert

Platform vs point solution

200 buyers called the rip-and-replace pitch crazy

Selling the platform one piece at a time

Why startup customers were false validation

Three land motions instead of an a la carte menu

Vibe coding, outsourced SDRs and enterprise bake-offs

Lightning round

Resources

Full show notes: https://saasclub.io/499

Join 5,000+ SaaS founders: https://saasclub.io/email

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