Join Pete in conversation with Marty Kausas, Co-Founder and CEO of Pylon, the Modern B2B Support platform.
Marty and Pete discuss Pylon's unique "Slack-based sale," Marty's early "Anti-sale sale", and Pylon's wild success at "Founder-Led LinkedIn Content" pipeline generation.
Marty's successful founder-led sales efforts powered Pylon to north of 100 customers and millions of ARR before hiring additional sales staff. All of which powered the organization to raising more than $20m from amazing investors like Andreessen Horowitz, General Catalyst, and more.
More on Pylon here: https://usepylon.com/
Sales motion details: Modern B2B Support Platform, Series A and B B2B software companies, customer success and support leadership, five-figure ASP. Multi-month sales cycle.
Pylon: How the “Anti-Sale Sale” Scaled a Support Platform Built just for B2B to Millions in ARR
Executive Summary
When Marty Kausas and his co-founders came up with the idea for Pylon in November 2022, they were initially just looking for "the adventure" of building a company. Two and a half years later, this founder-led sales journey has resulted in millions in ARR, $20M+ in funding from blue-chip investors like Andreessen Horowitz and General Catalyst, and a modern B2B support platform that's changing how companies communicate with their customers. The breakthrough came when they identified a critical trend: businesses were moving support conversations from email to real-time messaging platforms like Slack, but lacked the tools to manage this shift effectively. This led to Pylon's initial product—a connector between Slack and ticketing systems—before evolving into a comprehensive platform that now serves 500+ employees. By sending 120 personalized LinkedIn messages daily across three founder accounts, closing 100 customers before hiring their first sales rep, and turning LinkedIn content into a powerful acquisition channel, Pylon demonstrates how founder-driven selling can create a foundation for sustainable growth.
Key Metrics
Current ARR: Mid-seven figures
Average Deal Size: $10,000 (ranging from $1K to $15K+)
Sales Team: 5 Account Executives, 2 SDRs, 1 RevOps lead, 1 Growth Marketer
Target Market: B2B companies with 50-500 employees
Funding: $20M+ from Andreessen Horowitz, General Catalyst, Y Combinator
Customer Profile: Support and success teams in growing B2B companies
Problem Discovery: Finding the Gap Between New Communication and Old Support Tools
Marty's approach to finding a startup idea wasn't about personal passion—it was methodical and analytical. "We set a goal for ourselves to build a $10 billion plus public company in 10 years," he explains. This ambitious target shaped their entire search process.
After graduating in computer science and working at Airbnb, Marty spent two years pivoting through multiple failed ideas before landing on what would become Pylon. Their breakthrough came from a deliberate strategy: they analyzed the characteristics of companies that reached $10B+ valuations and found they were predominantly horizontal platforms in massive markets.
"We looked at Salesforce, the biggest SaaS company in the world, and their biggest revenue driver—Service Cloud at $9 billion per year—and said that's a good market to go after," Marty explains. But rather than just building another support platform, they went hunting for emerging trends within that space.
Their research approach was surprisingly straightforward but incredibly effective. Each founder would send 40 personalized LinkedIn messages daily to people with titles in customer support, asking for 15-minute calls to learn about their work. During these conversations, one pattern kept emerging: companies were moving their B2B communications away from email to conversational channels like Slack and Microsoft Teams.
This shift was breaking critical business workflows. "When you're chatting with someone in a shared Slack channel, no activity syncs to your CRM," Marty recalls. "You can't open support tickets from conversations happening there."
What really validated the opportunity was discovering that customers loved these new communication channels, but businesses struggled to scale them. Marty shares a telling example: "One vendor had promised Netflix a shared Slack channel in their contract. The next year, they tried to quietly remove this offering, and Netflix immediately called them out on it." Companies were stuck supporting a communication channel they couldn't effectively manage.
The insight that changed everything: businesses needed a bridge between modern communication channels and traditional support infrastructure. Their initial product became a connector between Slack and Zendesk—a narrow but powerful wedge into a massive market.
Early Sales Development: Getting to Yes When There's No Sales Experience
None of Pylon's founders had sales experience. Marty was a software engineer with zero background in selling, which made their approach refreshingly straightforward: just ask questions until someone admits they have the problem.
"The discovery process was mostly just asking questions, which I like doing anyway," Marty explains. This curiosity-driven approach removed much of the intimidation around selling. Rather than trying to convince prospects to buy something, they simply tried to understand whether they had the problem Pylon solved.
Their first customer came through an almost comical coincidence. After brainstorming the Slack connector idea with his co-founders, Marty hung up the phone and walked upstairs in his hacker house to find Tejas, co-founder of Hightouch, sitting on the couch. "I asked if they had this problem, and he said, 'Marty, you're not going to believe it, but we're actually looking for a solution right now.'"
The pricing conversation with Hightouch revealed both their inexperience and the market's hunger for a solution. "We hopped on the call and they asked, 'What's the pricing?' We said '$15K' with no rationalization," Marty recalls. Hightouch, knowing they'd be the first customer, negotiated down to $2.7K. "They really got us, but we were so happy to have our first customer."
One mental model that transformed their early sales approach came from reading "The Mom Test," which taught them to validate demand by asking direct questions about willingness to pay. "We started asking people not just 'Would you use this?' but 'Would you pay $10,000 on Monday once we have it ready?'" This immediately cut through politeness to real interest.
Another breakthrough tactic: moving prospects to Slack channels as quickly as possible after the first call. "Email was a place where conversations would die. LinkedIn had too much noise. But if we could open a shared Slack channel with a prospect, it dramatically increased our odds." This approach not only mirrored the product's value but created a persistent connection to prospects that email couldn't match.
Skills Building: Learning Sales Like Learning Code
Marty approached sales skill development the same way he'd tackled programming problems: break it down, practice systematically, and learn through repetition.
"The way we found our initial customers was LinkedIn outreach—each of us sending 40 personalized messages per day," he explains. While the quantity was important, the quality of these messages evolved based on what worked. Rather than pitching their product, they positioned themselves as founders trying to understand the space.
Pete Kazanjy's "Founding Sales" became their go-to resource, with Marty keeping it "open in a browser tab constantly" for reference. But the most valuable learning came from simply doing more sales conversations and making incremental improvements.
One key insight that accelerated their learning: focusing on getting to "no" as quickly as possible. "You should anti-sell your product quite early," Marty advises. "Give all the reasons why someone wouldn't use your product. If they really have the problem, those reasons won't matter."
This approach flipped the traditional sales mindset on its head. Instead of trying to convince everyone to buy, they worked to identify the small percentage of people who genuinely needed their solution—then focused all their energy there.
The founders' technical background actually became an advantage as they developed their sales motion. "We treated sales like debugging code," Marty explains. "When something isn't working, dig into why." This systematic approach helped them identify and fix specific issues in their process rather than making random changes.
Their biggest early sales skill breakthrough? Moving from "sell what we've built" to "sell before build." As Marty puts it, "Especially if you're coming from an engineering background, you should definitely try to sell your product before you build it." This approach dramatically accelerated their learning cycle and product development.
Sales Process Evolution: From Living Room Fishing to Systematic Sales
Pylon's sales process evolution followed three distinct phases, each addressing the limitations of the previous approach.
Phase One: The Hacker House Phase (0-15 customers) The earliest days were characterized by pure founder hustle. "First three customers were all in our network," Marty recalls. "One was someone who had tried to recruit my co-founder. Another was a former coworker of my other co-founder who had started their own company."
For the next set of customers, they doubled down on LinkedIn outreach, sending personalized messages to support leaders at companies sized 50-500 employees. Each successful connection led to a discovery call, followed by a product demo, then a shared Slack channel to continue the conversation.
"These weren't quick closes," Marty admits. "It was typically three 30-minute calls plus ongoing Slack communication to get them started." Product limitations meant constant troubleshooting, with the team sometimes building features on the fly between calls to meet specific customer needs.
Phase Two: The LinkedIn Content Era (15-50 customers) The game-changer came when they discovered LinkedIn content as a lead generation tool. "We had one post take off about our founder journey and building in public," Marty explains. "It got 300K+ impressions, and suddenly prospects were mentioning seeing us on LinkedIn."
They pivoted their strategy to focus on building relationships rather than immediate sales. Instead of pitching in connection requests, they'd send simple messages like "CS network" or "Founder building in CS" with a wave emoji. The goal shifted to building a network that would see their content over time.
"We'd send that, get them into our connections list, and then they'd see our content forever until they needed the tool," Marty explains. "We know all these people need the tool eventually. It's just a matter of time."
Phase Three: The Platform Expansion (50+ customers) As they evolved from a connector into a full support platform, their sales motion became more complex but also more valuable. They added proper sales tools—Salesforce replaced Notion as their CRM, they implemented Cal.com for scheduling, and built systematic pre- and post-demo sequences.
This phase also saw them shift from pure outbound to a mix of inbound and outbound. "A lot of our business today is inbound," Marty notes. "People book demos on our calendars directly, which compressed the number of meetings needed." This shift drove efficiency but reduced control over the types of companies they engaged with.
The evolution wasn't always smooth. Marty admits they overinvested in automation too early: "I had this crazy complex Clay table doing a bunch of stuff. I spent so much time trying to perfect this machine, but just sending personalized messages myself worked so much better."
Customer Acquisition Strategy: The Power of Founder-Led Content
Pylon's primary customer acquisition channel evolved from direct outreach to content-driven awareness, with LinkedIn becoming their dominant pipeline source.
The inspiration came from a fellow YC founder who mentioned LinkedIn was producing quality leads for his construction payroll company. "At the time, he probably had 5K followers and we thought 'Wow, that's so many,'" Marty laughs.
Their early content attempts failed to gain traction, but persistence paid off. "After a few months, we had one post about our founder journey that really took off," Marty recalls. This success helped them identify what resonated—authentic stories about building the company and solving problems.
The breakthrough strategy combined content marketing with relationship building. Rather than sending sales-focused connection requests, they shifted to building a large network first. "We'd send connection requests with simple messages like 'CS network' or 'Founder building in CS'—just enough to get accepted without pitching."
This approach created a powerful flywheel. Each connection saw their content in their feed, and when the time came that they needed Pylon's solution, they were already familiar with the company. "We know all these people need the tool eventually. It's just a matter of time before that day comes," Marty explains.
As their audience grew, they started hearing "I saw you guys on LinkedIn" from prospects and customers regularly. This validated their approach and helped them double down on content creation.
When asked what creative campaign really moved the needle, Marty points to their authentic founder journey content. "Just sharing how quickly we built our MVP with photos of the founders and storytelling—that post got 300K impressions and started everything."
As the company has scaled, they've begun diversifying beyond LinkedIn. "We're starting to invest in outbound now," Marty shares. "We have AEs starting to outbound, we've hired our first SDRs, and we're building more systematic processes around target account lists."
Timing & Compelling Events: Riding the Wave of Communication Platform Shift
Pylon's timing advantage came from identifying a fundamental shift in how businesses communicate—the move from email to real-time messaging platforms—and building a solution before most companies recognized the need.
"Slack Connect had only come out maybe two or three years before we started the company," Marty explains. "We'd heard of many YC companies who tried this idea before and failed. Our thesis was that the timing was wrong—they were too early."
What made timing particularly important was the network effect of this communication shift. As more companies adopted Slack for external communication, the need for Pylon's solution grew exponentially. Each new deployment expanded the network of companies exposed to this way of working.
This created a viral growth component: "Imagine Hightouch installs Pylon into all their shared Slack channels. All of their customers then see it and become familiar with the tool," Marty explains. "We've even had our customers' customers go tell their other vendors, 'Hey, you should use Pylon to make sure our tickets are tracked.'"
Rather than focusing on a specific compelling event like a compliance deadline or budget cycle, Pylon's opportunity was tied to a broader platform shift. Companies implementing Slack or Teams for external communication inevitably hit scaling challenges—precisely when Pylon's solution became critical.
Marty saw this trend accelerating: "The whole mentality on Slack has definitely changed. It's naturally become such a common way of operating that people don't question it anymore." By positioning themselves at the forefront of this shift, they created their own compelling event.
Pricing & Positioning Evolution: From $15K Guesswork to Structured Tiers
Pylon's pricing journey involved at least ten iterations as they refined their model and expanded their product offerings.
Their first pricing attempt was memorably awkward. "We had a call coming up with Hightouch to discuss pricing. We knew they wanted the product and that we were the preferred vendor," Marty recalls. They asked a YC partner for advice, who told them to "just make something up" and suggested pricing high enough to make themselves uncomfortable.
"We tried to go $15K ACV for our first customer," Marty says. "But they negotiated us down to $2.7K. They really got us." This experience taught them a valuable lesson about anchoring prices and the reality of early customer leverage.
As they evolved, their pricing model changed to match their product. "When we were focused on Slack, we did channel-based pricing—$5 per channel per month with some minimum," Marty explains. This created a clear value correlation: more channels meant more value.
But this approach hit a roadblock when they expanded their platform. "We introduced email support, which has no channels. What if someone's more email-based than Slack-based?" This led them to adopt seat-based pricing aligned with industry standards.
"We wanted to make it easy for people evaluating both Zendesk and Pylon. It would be a simple decision based on product value and features rather than pricing," Marty explains. This initially meant a flat $70 per seat per month with no tiers.
Their pricing gradually became more sophisticated: "First we had one tier, one seat. Then we introduced a second tier of seat. Then a third tier. Then we introduced add-ons like Microsoft Teams integration." Eventually, they incorporated AI capabilities as premium features.
Today, they position themselves as a consolidation play: "If they want AI agents or assistance, they'd otherwise have to buy another product. We try to price our variant the same or cheaper than the point solutions they'd have to purchase."
Customer Success Philosophy: Slack as a Superpower
Pylon's customer success approach centers on using their own product as a communication channel—a strategy that creates both tremendous value and a powerful demonstration effect.
"We have probably 1,500 Slack channels now with both prospects and customers, which is insane," Marty shares. "With Pylon, it's super scalable and it doesn't matter." This approach gives them all the benefits of real-time communication without the traditional downsides of unstructured conversations.
Their AEs "dog food" the product daily as a pre-sales tool, which provides constant feedback for improvement. "Even though it's not built for pre-sales, it functions as an inbox for managing shared Slack channels," Marty explains. This creates a seamless experience where the sales process mirrors the post-sale relationship.
"If you think about what customer success and account management do post-sales versus what a salesperson does pre-sales, they're very similar at Pylon," Marty notes. "You're collaborating with engineering, asking for certain features, sending product feedback directly to engineers—and you do it all through Pylon."
This approach creates natural expansion opportunities as customers experience the value of unified communication channels. It also builds stronger relationships through persistent, low-friction communication.
The biggest customer success mistake they made? "Not hiring CSMs/support soon enough," Marty admits. "We got so many customers with no CSM and were totally over
