After achieving repeatability, the founder/CEO has a 'second job.' They must stop building and selling the product themselves and start building the company that does it for them. This means shifting from being the PM of the product to becoming the PM of the company.

HubSpot co-founder Brian Halligan observes a new archetype of tech leader: the "five-tool CEO." Like a rare multi-talented baseball player, they possess elite skills in five key areas: vision, coding, design, recruiting, and sales. Founders like Rippling's Parker Conrad exemplify this new, formidable breed of entrepreneur.

Brian Halligan reflects that as HubSpot grew, he was coached out of his natural 'founder mode' instincts (e.g., many direct reports, public feedback) and into conventional 'manager mode' (weekly one-on-ones, private criticism). He now regrets this shift, believing his initial, more unconventional approach was more effective.

Brian Halligan graded his performance and happiness as CEO based on company size. He felt most effective and enjoyed his work most in the 10-1,000 employee range, focusing on customers and employees. Beyond that, the work became less interesting and more administrative, suggesting a founder's ideal stage may be finite.

Around the $5 million revenue mark, a founder's primary responsibility shifts from operational tasks to talent acquisition. This transition to becoming a "collector of people" is often jarring but essential for scaling further, mirroring the biblical "fisher of men" concept applied to business.

Tariq Farid shares his grandfather's wisdom: "brawn to brain." In a company's early days, a founder's physical work ("brawn") is crucial. As it matures, their value shifts to wisdom, strategy, and system-building ("brain") to enable scale and prevent burnout.

Despite success, founder Kevin Wagstaff felt like an "imposter" as the company scaled beyond $10M ARR. He recognized his strengths were in the early, scrappy "bias to action" phase, not managing a larger organization. He proactively brought in a seasoned CEO better suited for the next stage of growth.

An engineering background provides strong first-principles thinking for a CEO. However, to effectively scale a company, engineer founders must elevate their identity to become a specialist in all business functions—sales, policy, recruiting—not just product.

Brian Halligan, HubSpot's longtime CEO, observes that the established rules for corporate leadership are obsolete. He cites unconventional leaders like Elon Musk, Nvidia's Jensen Huang (with 60 direct reports), and Airbnb's Brian Chesky as examples of innovators who are successfully rethinking company management from scratch.