Intercom

Intercom was a massive success story. By the early 2020s, it had grown to hundreds of millions in ARR over 14 years, building the dominant customer communication platform. But Owen McCabe's personal health crisis and his departure from the CEO role in 2020 created a vacuum. While he was away, the company became bloated, unfocused, and lost its energy. They were trying to be everything to everyone—customer service, outbound messaging, SDR tools—and it showed. By late 2022, the business was in freefall: five consecutive quarters of declining net new ARR, trending toward negative growth. "We were about to hit zero dollars net new error, which means we would have been in negative growth territory," McCabe recalls. When he returned to the business he'd built, he found a company that had betrayed its original mission and lost its spark.

When ChatGPT launched in November 2022, Intercom had already assembled a small AI team working on rudimentary bots and ML-powered Q&A for support. But GPT-3.5 was different. "We had a bunch of our own machine learning that did Q&A for customer service, but it required a phenomenal amount of setup and was kind of crappy," McCabe admits. Within six weeks of GPT-3.5's release, the AI team had a working prototype of what would become Fin. Des, his co-founder, sent McCabe a text: "The AI team have something interesting. They actually think we could make a product out of this."

The timing couldn't have been better—or worse. Intercom was hemorrhaging growth. They had no choice but to go all-in. McCabe and his co-founders committed to spending nearly $100M of their own cash on the AI bet. "We certainly are unique. I don't know a single company of our size and age that has pivoted this hard to AI and being as successful as we have been, but we also previously were screwed. We ran a really tough spot, so had no choice."

Intercom had a massive existing customer base—30,000 paying customers, hundreds of thousands of active users, and billions of data points. This was gold for training an AI agent. Fin launched at $0.99 per ticket resolved, a price McCabe chose deliberately. "We were spending $22 per ticket resolved. We thought, can we charge $10? Can we charge $5? Can we even charge $2.50? But we knew people just wouldn't value the digital work as much as human work, even though it's better. So we landed on $0.99—the nexus between us earning margin and it being palatable."

The pricing strategy was backed by McCabe's painful learning from Intercom's past: their old pricing was so confusing and expensive it became a viral meme on Twitter. McCabe had just given away ~$50M in ARR simplifying prices for existing customers. With Fin, he got it right from the start: simple, outcome-based, fair.

Fin's success wasn't just about product—it required McCabe to remake the entire company. He moved into what he calls "hardcore founder mode": top-down, dictatorial, unforgiving. He picked a single lane (customer service), killed all other projects, and slashed costs aggressively. "I said, we're doing service. Forget all the other stuff. Even though there was a lot of people in the company saying, oh shit, we still have $80 million of ARR from the other thing." He scrapped the old culture and rewrote the company values to emphasize resilience, high standards, hard work, and shareholder value. He implemented hard-coded quarterly performance reviews with a formula: miss the mark on goals or values, and you're out.

This caused massive upheaval. There were letters to the board. A soft coup attempt. But it worked. "Ultimately, like 40%" of employees turned over. Those who left were generally the ones who wanted a gentler, more collaborative culture. Those who stayed became "the most incredible entrepreneurial, brave, inspiring, happy individuals." Fifteen months in, an anonymous employee survey showed 98-99% approval of leadership and strategy—despite McCabe having the lowest Glassdoor rating when he returned.

Fin itself grew explosively: from $1M to $12M ARR in year one, then into "solid, mid eight-digit ARR." It's now on track to pass $100M ARR in less than three quarters. "We're like in the 15th percentile for ARR growth" among public SaaS companies. Fin is the largest AI agent in customer service by customer count and revenue, rated #1 on G2, and wins every competitive bake-off.

Intercom has become a case study in disrupting yourself before someone else does. McCabe's core lesson: "You don't have a choice. AI is going to disrupt in the most aggressive, violent ways. If you're not in it, you're about to get kicked out." But he's realistic about the cost. "If you want to compete and enjoy success in this age, you need to be doing AI, and that is their price. So you either decide to pay the price or get out." He practices what he preaches, working intensely to keep up with the scrappy 20-something founders who are building AI companies working 12 hours a day, 365 days a year.

McCabe sees a future where organizations are a medley of humans and agents, with agents handling repetitive work while humans focus on judgment, creativity, and connection. For Intercom specifically, this means the customer service category is about to be completely remade by AI—and Intercom, once nearly dead, is leading the charge.