The Startup CEO Playbook
This guide is for founder-CEOs from pre-seed to about Series A. It covers the three jobs that never go away, direction, team and cash, and the habits that make them work: founder-led sales, a one-page strategy, a weekly operating rhythm, runway discipline, clear decisions, a strong leadership team, a well-managed board and a deliberate culture.
What makes a good startup CEO?
Not a personality type. Good startup CEOs set a clear direction, build a team that can deliver it, never let the company run out of money, and change their own job as the company grows. Most CEO problems come from doing the previous stage’s job for too long. Start with what a startup CEO does.
| Plan | |
|---|---|
| Priority | 6 mid-market deals |
| Not doing | Enterprise RFPs |
| Hire | VP Sales |
| Section | Status |
|---|---|
| Highlights | 2 deals |
| Lowlights | 1 churn |
| Asks | 3 intros |
Related guides cover the specialist work: raising money in Pitch Decks and Fundraising, ownership in Startup Equity, people operations in Startup HR and marketing in the Fractional CMO Playbook.
Where should you start?
Sell first, set the priority, build the rhythm, guard the cash, then build the team around you. Each card opens the page for that step.
First 10 to 20 customers.
Teaches: the marketSee the pageAnd a not-doing list.
Creates: focusSee the pageTime where only you can.
Frees: hoursSee the pageScorecard and meeting.
Catches: problemsSee the pageDefault alive or dead?
Avoids: surprisesSee the pageReversible or not.
Removes: bottlenecksSee the pageBuilders, not titles.
Scales: the companySee the pageMonthly updates.
Builds: trustSee the pageWorking with a co-founder? Read co-founder relationships. Growing the team? Read culture and communication.
The job
What a startup CEO does at each stage, why the CEO sells first, and where the week should go.
The CEO’s three jobs, and how the role changes from pre-seed to Series A.
Read guideSell the first customers yourself, then hand off a process that works.
Read guideAudit the calendar, delegate the right things and protect time for priorities.
Read guideRun the company
Strategy and goals, the weekly operating rhythm, cash and runway, and how decisions get made.
A one-page strategy, quarterly goals a small team can use, and a not-doing list.
Read guideA weekly scorecard, a few good meetings and a quarterly planning rhythm.
Read guideBurn, runway, default alive or dead, and when to raise or cut.
Read guideReversible versus irreversible decisions, clear owners and a decision log.
Read guideLead the people
The leadership team, the board and investors, the co-founder relationship, and culture.
When to hire executives, who to hire first, and how to avoid VP hiring mistakes.
Read guideBoard composition, board meetings, monthly investor updates and delivering bad news.
Read guideDivide roles, disagree well, spot warning signs and handle a co-founder exit.
Read guideValues that guide decisions, all-hands meetings and a writing culture.
Read guideDo this stage’s job, not the last one’s.
The habits that got the company to its first customers are rarely the ones that get it to Series A. Change your own job as the company grows.
Frequently asked questions
What does a startup CEO do?
Sets direction, builds the team and keeps cash in the bank, plus selling and recruiting in the early stage.
Should the startup CEO do sales?
Yes, for the first customers, until there is a repeatable process to hand off.
How should a startup CEO spend their week?
On customers, hiring, cash and the quarter’s priority. A calendar audit shows where time really goes.
What is default alive?
A startup that will reach profitability on current growth and spending before its cash runs out.
How often should a CEO update investors?
Monthly, with highlights, numbers, lowlights and asks.
When should a startup hire executives?
When a function has a repeatable process to scale and the CEO has become the bottleneck.
Sources & further reading
These primary sources let you read the original ideas this guide builds on.