What’s the Second Job of a Startup CEO?

Spot on, and it's really really hard. I had the privilege of working for a CEO who scaled his business from < 20 people when I joined to ~300 when I left. You really feel each of these stages and it's very difficult to ride the transitions through them, especially if you've done a good job in phase one and you have strong product fit with your market, the business kinda just gets sucked along for a while and it's hard to "feel" the break points if you will. There is a transition from the tactical CEO to the thoughtful CEO that is hard to describe and seems hard for many of the CEOs I coach to execute. Not transitioning quickly enough through these stages and steps, and remembering to somewhat modulate your message regarding the vision mission and purpose stuff results in very uncomfortable periods of time, especially uncomfortable if your company has caught up to your thought. I do think CEO at scale is an incredibly difficult job.

I wish this piece had spent more time on the art of "Making Sure They Work Well Together." This is huge -- and underappreciated by 95% of founders. Here are four dimensions that would be worth exploring in a subsequent post:

Who does what? What happens when we disagree? What are the ground rules for revisiting a decision? Do we understand one another's approach to time management, prioritizing, delivery targets, conflict resolution, etc.

Members of the early-stage leadership team aren't clones. There will be differences. Can we calibrate smoothly, or will we forever need to "talk it out"? When there's a lot of churn in the founding team, usually it's because one of these four issues isn't being handled well. In severe cases, cycling new people into the job just starts the fail loop afresh -- no matter how amazing each new candidate might be.

This took me a year to really internalize- I wish I had read this a while back when we were 20 people. It wasn't until we passed 45 that I really took a thorough look at how I was spending my time. I intellectually understood the transition to delegation and leverage but a lot of the rest of the company didn't and it caused me to take longer than I should have to refocus on recruiting an exec team and defining the company strategy. Excellent writeup.

This essay is absolutely fantastic - one of the best pieces of writing I've ever read on growing a company. The description of the phase one/two/three CEO Model makes a ton of sense, and the examples given (SpaceX mission, Pixar culture) were enlightening.

I have just one criticism: I think the headline under-sells the rest of the essay. I see this more as the YC guide to growing your startup beyond phase one.

I took me a while to figure this out but i agree with Ali. However, i'd argue that as a CEO with a product background (the same probably goes for engineering) you can still spend time with your product teams through Phase 2 and maybe even in Phase 3. It is just a slightly different role, a more guiding function.

The second thing a CEO should focus on is building a repeatable sales model. Some products "sell themselves" but most products need a lot of experimentation with the sales model until they become profitable.

The second job of a startup CEO is actually everything outside of building a product. Everything from hiring the right team, to making sure people are happy, to finding sales/distribution channels, marketing channels. It's not a question of what else the CEO should be doing but a question more of how long he/she should be doing those things.

My three priorities when I was a CEO: Team, Vision, Cash.

Easier said than done.

> Doer-in-Chief. You must be deeply involved in both building the product (observing/interacting with users, writing code, designing product specs)

I slightly disagree here, I would rather start with the Second Job or Phase 2, 'Hiring a Leadership Team and Making Sure They Work Well Together'. The more you focus on finding and setting up the best team early on the better. You can do yourself a prototype, write code or do market research to see if you are on the right track. However, I recommend to setup the founding or leadership team before anything else. Once you have the team in place the project gets momentum and pace will be 100x compared to before. And finding the team plus setting up all legal matters will be a full-time job your first weeks if not months.

The stereotypical image of the CEO is that they are Backslappers and they play golf.

Not so in Silicon Valley I suppose.

The main factor I see for CEOs in a startup is Time horizon. If you want to be around for thirty Years, have fun, and incidentally build a useful Product - you will do things differently.

The Steve Jobs/ Sun Tzu type of anecdote is the best. If you spend 50 percent of your time on strategy or Thinking, it is for the best.

A final point is that keeping a good attitude is Important, not just for you but also for your team. This is often underestimated.

I'm not so sure about the implicit assumption that growth/phase change should be measured by head count. Sure you need some estimate but I do find the stage3 = 400 employees a bit strange. Especially given WhatsApp happened.

I would have preferred if the article used some other measures to indicate the state changes (profit, net promoter whatever) or at least discussed this a bit more.

That being said it's a pretty good article. I think it makes the product/market fit -> company building shift pretty clear.

Why did YCombinator blog switch to Wordpress from their own "free forever" Posthaven solution?

Their new site feels tacky and generic kinda like this blog post. Taken together with less news on larger batches of startups in recent years, it feels symptomatic of a slow dilution/degration of the YC brand.

Caveat, I'm not the CEO of a company, but I feel like the priorities in this are wrong (but maybe I don't strictly prescribe to the SV/startup mentality). At first, especially if you are technical CEO, it makes sense to build the product either alone or with your CTO/co-founder. However, I wouldn't consider this a "first job" because while it's necessary at the beginning it isn't the job of a CEO. For example, this post says, "Delegation should not be a word in your vocabulary." This is really not true; good leaders and those who get lots of things done are the ones who can delegate extremely efficiently and who can trust those they delegate to do get the job done. In my opinion, building the product is maybe 10% of the job of a CEO, even in the beginning. The 90% of the job is actually building the company, building the brand, getting the word out, delegation.

I would say that the first job of a CEO is building the company, the second job is building the product. If I have time after all of my other priorities were done, then I would help with the product (as in commit code, create or collab on a design or product workflow, etc.). The title CEO isn't just a random arrangement of letters: sure, it's fine to be part of the product in the beginning when there's only a couple or few people, but once it moves beyond that (and not at the 20 person level like this post says) the CEO should really trust that the CTO and the product team can do their job while the CEO handles all the other non-product aspects.

Lol. The job of a CEO is to implement the will of the board, of the people who actually own the company. It is normal for startup CEOs to also be an owner, or to know them all socially, but that doesn't mean they aren't a CEO.

If the board wants to expand, the CEO works to expand. But increasingly boards fear rampant expansion. Some aren't looking to cash out via an IPO or buyout. That path is becoming exceedingly difficult. Some want to see profit much earlier. I know one startup with TWO customers, big customers, that is totally focused on them and isn't seeking to grow. That board places customer focus above anything else and instructs their CEO accordingly. He isn't happy. His dreams of rampant expansion and market dominance have been quashed, but he is still doing his job as CEO.