Finding Meaning Despite Corporate Pain

Situation

Company context: Intercom was a 14-year-old SaaS business with hundreds of millions in ARR, but growth had slowed to low single digits
Leadership crisis: Owen McCabe (founder/CEO) had left the company in 2020 due to health issues (mold toxins, tick bite) and burnout
Business decline: After his departure, the company faced five consecutive quarters of declining net new ARR, approaching zero growth
Personal state: Despite wanting new adventures, Owen still felt pride and connection to the company he had built
Timing: Owen returned as CEO in late 2022, just one month before ChatGPT was released

Rapid prototype: Within six weeks of ChatGPT's launch, Intercom had a working beta version of Fin (their AI agent)
Leveraged existing assets: Used their large customer base (30,000 paying customers) and existing AI team as advantages
All-in commitment: Allocated nearly $100 million of their cash to the AI transformation
Pricing innovation: Created outcome-based pricing (99¢ per resolved ticket) despite initially losing money on each transaction

Authoritarian approach: Implemented top-down, founder-led decision making rather than consensus-building
Strategic focus: Narrowed strategy to customer service only, abandoning other product lines despite internal resistance
Value reset: Rewrote company values to emphasize resilience, high standards, hard work, and shareholder value
Performance management: Implemented quarterly performance processes with hard-coded formulas for both goal achievement and value alignment
Workforce change: Approximately 40% of employees turned over during the transformation period

Embraced vulnerability: Returned with greater self-awareness after his burnout and "ego death" experience
Therapeutic growth: Credited 12 years of therapy with helping him remove counterproductive edges while maintaining effectiveness
Renewed purpose: Found meaning in the transformation despite the daily challenges of corporate leadership

Business transformation: Fin (AI agent) grew from $1M to $12M ARR in its first year, now at "solid mid-eight digit ARR"
Growth acceleration: Intercom moved from low single-digit growth to the 15th percentile among public software companies
Market leadership: Became the largest AI agent in the customer experience category by customer count and revenue
Future trajectory: On track to pass $100M ARR with Fin in less than three quarters
Cultural alignment: Anonymous employee survey showed 98-99% approval of management, leadership and strategy
Personal outcome: Found deep meaning in the transformation despite ongoing challenges of corporate leadership

Decisive action trumps consensus: "The way that greatness is created is that you find a CEO who's willing to make brave hard decisions and own the results"
AI requires full commitment: "You don't have a choice. AI is gonna disrupt in the most aggressive violent ways. If you're not in it, you're about to get kicked out of all of it"
Talent acquisition is critical: "We would be nothing if we didn't have actual AI scientists and leaders"
Competitive intensity: "All these little AI companies run by kids in their twenties are literally working twelve hours a day, literally 365 days a year"

Founder mode effectiveness: When transformation is needed, top-down decision making may be necessary despite resistance
Employee-founder fit: "You have to have the right employees for the type of business you're creating"
Leadership development: Therapy and self-awareness can remove counterproductive edges while maintaining effectiveness
Finding meaning in difficulty: Even when daily work is challenging, connecting to a broader mission can provide purpose
Ego management: "When you acknowledge [your ego] then it's not a surprise when you're a little jealous... and it's all good"