How to be a CEO when AI breaks all the old playbooks | Sequoia CEO Coach Brian Halligan

Brian Halligan, co-founder of HubSpot and now a CEO coach at Sequoia, observes that while it has never been easier to start a company, scaling one has never been harder due to immense competition and noise. The CEO’s role has evolved, demanding faster, better decision-making and a willingness to abandon optionality in a rapidly changing environment.

On Hiring and Building Executive Teams

A primary focus for CEOs of scaling companies (over 100 employees) is building their executive team, with many spending up to 50% of their time on recruiting and interviewing.

• Interviewing and Referencing: CEOs consistently overrate their gut feeling in interviews and underrate the value of high-quality, blind references.

  • An Interview Hack: Parker Conrad’s method of sending a board deck under NDA to a C-level candidate and discussing it for 30 minutes is highly effective. It reveals whether the candidate is a challenger or a “yes person.”
  • Better Reference Questions: Instead of asking for strengths and weaknesses, ask questions like, “Would you enthusiastically rehire this person for that role?” or “On a scale of 1 to 10, how likely is it that you’ll try to rehire this person back from me down the road?”

• Hiring “Spiky” Candidates: HubSpot shifted its hiring strategy from consensus picks (where everyone rates a candidate a 3 out of 4) to “spiky” candidates—those with clear strengths and acknowledged weaknesses (e.g., a mix of 4/4 and 2/4 scores). These individuals often bring unique value and challenge the status quo.

• Homegrown Talent vs. Big Company Hires: There’s a “massive impedance mismatch” when startups hire executives from large corporations like Microsoft or Google. These hires often have misaligned expectations and a high attrition rate. It’s better to build a team like the 2004 Red Sox: a core of high-quality, homegrown talent complemented by a few strategic external hires. If it’s a close call, give the internal candidate the shot.

The Anatomy of a Successful CEO

Halligan uses a mental algorithm called “LOCKS” to evaluate founders:

• L - Lovable: They inspire followership. You’d want to “crawl across broken glass” to work for them.
• O - Obsessed: They have deep founder-market fit and a long-term obsession with the problem they’re solving.
• C - Chip on the shoulder: They possess a powerful inner drive, like a “boulder on their shoulder.”
• K - Knowledgeable: They have deep domain expertise.
• S - Student: They are “students of the game,” constantly learning like an LLM, not just from peers but from history.

While some traits may be innate, several critical skills must be learned on the path from startup to scale-up. The most common and difficult skill for new CEOs to learn is giving direct, constant feedback.

The Future of Go-to-Market (GTM) in the AI Era

The GTM funnel is being turned on its head. Enterprise sales, which relies on trust between “carbon-based life forms,” will likely be the last white-collar job AI replaces. However, the process leading up to it will change dramatically.

• The New Discovery Funnel: Buyers will conduct initial research within LLMs like Gemini and ChatGPT, making traditional websites less important as the primary entry point.
• The Rise of Avatars: Websites will evolve to feature intelligent avatars that can hold high-quality conversations about products, pricing, and company information.
• The Augmented Sales Rep: Sales calls will be augmented by AI. A sales rep will bring their own “SE avatar”—an all-knowing assistant—to every meeting, eliminating the need to wait for a human sales engineer.
• The First Movers: The top of the funnel will change first, requiring a new focus on getting found in LLMs (what one might call “AEO” or AI Engine Optimization) and building websites for conversational engagement.

“Halliganisms”: Core Operating Principles

These are memorable pieces of advice from Halligan’s tenure as CEO.

• “When you have to eat a shit sandwich, don’t nibble.”: When delivering bad news like layoffs, do it once and decisively. Rip the band-aid off instead of drawing out the pain with multiple small cuts.
• “Never waste a good crisis.”: The best changes often emerge from crises. After a major outage, HubSpot fundamentally rethought its software deployment and reliability, leading to significant long-term improvements. The key is to overcorrect and swing the pendulum hard in the other direction.
• “If you want to kill a plant, have two people water it.”: This illustrates the critical importance of a Directly Responsible Individual (DRI). As companies scale, ambiguity in ownership for cross-functional projects leads to failure. Every important initiative needs a single, empowered owner.
• “EV > TV > MV”: This formula stands for Enterprise Value > Team Value > My Value. It’s a reminder to prioritize the company’s success first, followed by the team’s, and finally one’s own. HubSpot embedded this into performance reviews and later added CV (Customer Value) at the very beginning of the hierarchy.
• No Silver Bullets: Success isn’t the result of a single hire, product launch, or event. The reality inside a scaling company is a constant grind of “two steps forward, one step back.”

• Tags:
• Go-to-Market
• AI Strategy
• Scaling
• Leadership
• Hiring
• Sequoia Capital
• CEO
• HubSpot