How to be a CEO when AI breaks all the old playbooks Sequoia CEO Coach Brian Halligan (Category Management)

Interesting. podcast Lenny, in which Brian Holligan came to him, co-founder and ex-CEO HubSpot. They discussed leadership and business in the age of AI: how to hire, grow and sell when old playbooks are bursting at the seams. Brian was CEO. 15 He now acts as an internal CEO coach at Sequoia and hosts a leadership podcast. Long Strange Trip.

The basic insights are like this

1Startup is easier than ever; scaling is harder than ever AI and clouds have greatly reduced the cost of launching, so the number of companies will soar to the skies in the coming years. 10 But noise and competition are making scaling and differentiation increasingly difficult.

2CEO Job → Infinite Hiring and Org Design Adult CEOs spend up to half their time recruiting, interviewing, and constructing an exec team, not a product or operating system.

3Everyone overestimates their ability to interview Instinct “I think he’s cool” is worth almost nothing; more important are hard blind references, work sessions with the candidate and the right questions about rehiring. n

4You need to hire "sharp" (spiky)Not consensus people. HubSpot has stopped using consensus.3/4 from all voices" and began to take people with strong pluses and noticeable minuses; it improved the hit-rate

5People from bigtech almost always do not come to companies at an early stage Hiring from Microsoft/Salesforce/Google for a company 50–500 A person often gives “impedance-mismatch”: the expectations of the process and resources do not coincide with the reality of a startup.

6Basic playbook - a team like Red Sox-2004Homegrown mix and a couple of stars
Most management grows from within, plus a few expensive veterans, not the McKinsey/FAANG carpet.

**7LOCK framework(S) foundationer

• L (lovable)**I want to follow him, he inspires his followers. **- O (obsession)**Deeply obsessed with the problem, strong founder-market fit - C (chip on the shoulder): an idiom about “holding a grudge,” when a person feels offended by a past insult or perceived injustice, then there is an intrinsic motivation to “prove.” It's interesting that I didn't know this idiom before and I like it. (I feel like I work best when I have that feeling.)
  - K (knowledge): In-depth knowledge of the domain
  **- S (student)**A fanatical student of the game, digging both history and modernity

8CEO may not be anyone, but at the same time they are not only born There are rare5Tool CEOs who know how to code, sell, inspire, have taste and vision (example Bret Taylor.)But most people have to pick up skills: feedback, BS, people's inspiration.

9Pain No.1 Founders - give feedback and change early employees
The hardest part is telling the cofounder/early head of X, “You’re no longer in control, you’re a visionary/CTO, and we’re hiring an operational leader over you” and doing it in a sustainable but tough way.

AI is already hitting hard on development and support, but not on enterprise sales Coding, support, legal are already transforming, and enterprise sales, where trust between two people is needed, will be the last in white collar to be replaced by AI. But in general, everyone will have their own personal agents, connected to the mail, calendar and notes, who can be called to rallies as an active participant, not just as a record.

And finally about the funnel go-to-market, which becomes focused on agents The funnel “Google → site → demo” will be replaced by “Gemini/Claude/ChatGPT → deep research → already educated client”. The site will become less important.
The site will have an “omniscient avatar” who understands the customer’s product, pricing and context, has a conversation and writes in CRM. Sales will have an avatar on the call that knows everything about the product and the customer and helps answer in real time.

In the sequel, I'll talk about what engineers and technical managers can learn from this talk.

#Leadership #Management #Software #AI #ML