Dear SaaStr: What Steps Did You Take To Become a CEO?

Dear SaaStr,
I want to become a CEO someday. Not “CEO of my group project,” but the real thing: building a company, leading a team, making the calls, and (apparently) drinking iced coffee while staring meaningfully out a window. What steps should I takestarting nowto actually earn the seat?

Sincerely,
Ambitious, Slightly Terrified, and Very Into Checklists

Dear Ambitious,
First: you’re not crazy. Second: you’re a little crazy (but in a healthy startup way). Third: becoming a CEO isn’t one giant leapit’s a stack of smaller, unglamorous reps that quietly build “CEO muscles.” Think of it like training for a marathon, except the marathon occasionally emails you at 2:00 a.m. with the subject line: “URGENT: churn + runway.”

Here’s a practical, real-world pathbased on patterns you see again and again across SaaS and tech: the roles people take, the skills they deliberately collect, and the moments that finally make them CEO-ready.

The Big Truth: CEO Isn’t a Crown, It’s a Job Description

A lot of people chase “CEO” like it’s a destination. But the title is just the label on the box. The box contains the job.

At most startups (especially SaaS), the CEO’s work tends to collapse into a few non-negotiables:

• Build something people truly want (or guide the organization that builds it).
• Build the company around itteam, culture, systems, and execution.
• Keep the company alivecapital, runway, customers, and credibility.
• Make the hard callspriority, tradeoffs, hires, fires, and strategy shifts.
• Represent the companyto customers, investors, partners, and the public.

If that list makes you think, “Wait, that’s… a lot,” congratulations. You’ve discovered the CEO role. It’s not a reward for being the smartest person in the room. It’s a commitment to being responsible for the whole room.

Step 1: Get Close Enough to the CEO Seat to See the Receipts

If you want to become a CEO, don’t just admire CEOs from afar like they’re rare birds. Get closeprofessionally. The fastest learning happens when you can observe real decisions in real time.

What “close” looks like in real life

• Roles that sit near leadership: chief of staff, ops lead, strategy, finance, legal, business ops, or running a critical function that reports directly to the CEO.
• Board exposure: not because it’s glamorous, but because it forces clarity. Board meetings are basically “explain your company to smart skeptics” practice.
• Cross-functional projects: anything that touches product, go-to-market, and execution at the same time.

One classic route is an “apprenticeship ladder”: you work alongside founders or CEOs in multiple contexts, watch them scale teams, survive crises, and communicate under pressure. This isn’t about copying their personality. It’s about learning the mechanics of leadership: how decisions get made when no option feels perfect.

Concrete example: If you’re a director running a revenue team, don’t just hit the number. Start noticing what the CEO notices: pipeline quality, retention risk, hiring needs, pricing leverage, and whether the story still makes sense to customers.

Step 2: Learn People Management (Because Adults Don’t Manage Themselves)

CEO readiness is painfully correlated with one skill: managing people. Not “assigning tasks,” but leading humans with fears, ambitions, blind spots, and Slack notifications.

If you want the CEO path, you need reps in:

• Hiring: defining roles, evaluating talent, and making calls with incomplete information.
• Feedback: saying the true thing kindly, clearly, and on time.
• Delegation: letting go without disappearing.
• Culture: reinforcing values through what you tolerateand what you don’t.

The “lead by example” trap

Early on, leaders often “lead by example” because it works: you’re in the trenches, people see your hustle, and everything moves. But as companies grow, that approach breaks. Not because hustle is badbut because the organization can’t scale on your personal output. Eventually, leadership becomes “lead by ideas,” meaning your clarity, priorities, and decisions shape what hundreds of people do.

Concrete example: At 10 people, you can personally answer every customer email. At 100 people, if you do that, you’re not heroicyou’re a bottleneck wearing a cape.

Step 3: Own Something That Has a Scoreboard

Want to be CEO? Own a number.

CEOs live in scoreboards: revenue growth, churn, retention, burn, runway, margins, customer satisfaction, velocity, and quality. The fastest way to build CEO instinct is to run a function where success is measurable and the tradeoffs are real.

Good “CEO-training” ownership areas

• Revenue: sales, partnerships, or a quota-carrying team.
• Retention: customer success, support quality, or product adoption.
• Growth: marketing that ties to pipeline and conversion (not just vibes).
• Product outcomes: shipping improvements that move activation, engagement, or expansion.

Concrete example: If you lead customer success for a SaaS product, you’ll learn how churn behaves, how onboarding fails, why “feature requests” often mean “I don’t understand your product,” and how renewals expose whether value is real.

Step 4: Learn Fundraising (Or at Least Learn the Language of Capital)

In startup land, the CEO is often the company’s primary translator: turning messy reality into a clear plan investors can trust. That’s why fundraising and CEO readiness overlap so much. It’s not just “pitching.” It’s proving you can think in systems and plan for risk.

What fundraising teaches you (even if you never raise a dollar)

• Clarity: What are you building, for whom, and why now?
• Strategy: How do you winand what do you stop doing?
• Metrics: What matters, what’s noise, and what’s improving?
• Runway discipline: How long can you survive, and what changes that?

Concrete example: Start writing investor-style updates (even if you’re not fundraising). A simple monthly notehighlights, lowlights, metrics, lessons, next month’s prioritiesforces CEO-grade thinking.

Step 5: Build Go-to-Market Muscles (Talk to Customers Like It’s a Subscription)

Many future CEOs fall in love with building and forget selling exists. Then reality shows up like: “Hi, I’m Reality. Your product is great. Your pipeline is not.”

CEO-ready leaders understand go-to-market:

• Positioning: what you do that’s different and why it matters.
• Pricing: capturing value, not apologizing for it.
• Sales motion: who buys, how they decide, and what stalls deals.
• Customer discovery: learning pain points early and continuously.

Concrete example: If you’re a product leader, sit in on sales calls. If you’re in sales, watch onboarding. If you’re in marketing, follow deals through close. CEOs connect the whole loop.

Step 6: Learn the Hardest CEO Skill: Managing Your Own Psychology

Here’s the part no one puts in the “10 Steps to CEO” carousel: the job is emotionally loud.

You’ll face uncertainty, loneliness, and decision fatigue. You’ll get praised for wins you barely caused and blamed for problems you inherited from physics. (Yes, physics. Timelines and budgets obey their own cruel laws.)

Build a personal operating system

• Decision hygiene: make fewer, better decisions; document reasoning when stakes are high.
• Truth-tellers: cultivate mentors, peers, and a team that can disagree with you safely.
• Energy management: sleep, exercise, boundariesbecause burnout is not a business strategy.
• Reflection loops: weekly reviews of what worked, what didn’t, and what you’ll change.

CEO success isn’t just intelligence. It’s emotional stability under pressurestaying clear when things are messy, and steady when things are scary.

Step 7: Take the Founder Path (If That’s Your Goal) in Smaller, Safer Reps

Many CEOs become CEOs by founding. But founding is a leapand leaps go better when you’ve trained your legs.

“Founder reps” you can do before going all-in

• Be the “owner” of an internal startup: a new product line, a new segment, a new motion.
• Build nights-and-weekends: a tiny tool, newsletter, micro-SaaS, or servicelearn distribution.
• Join early: be employee #5–#50 at a high-quality startup and grow with it.
• Take a founder-adjacent role: Chief Business Officer or COO can be a bridge into CEO.

The goal is to learn the full-stack reality: product, customers, people, cash, and tradeoffswithout relying on a title to grant permission.

Your First 90 Hours (Not Days): How New CEOs Win Trust Early

New CEOs often feel pressure to “make a mark” fast. But the smarter play is usually: listen deeply, map stakeholders, and build credibility before you swing big.

A practical first-90-hours checklist

• Meet your direct reports 1:1 and ask: “What must change? What must not change? What am I missing?”
• Talk to customers earlyespecially churned customers. They are brutally honest for free.
• Understand cash and runway immediately. Hope is not a line item.
• Align with the board on goals, constraints, and how success will be measured.
• Communicate your approach to the company: what you’re learning, what you’re prioritizing, and when decisions will come.

Trust is built when people feel seen, when reality is named clearly, and when priorities are consistent.

Three Common Paths to CEO (Pick the One That Fits You)

1) Founder CEO

You start the company. You earn the role by doing every job until you can hire people better than you. Your biggest challenge is scaling yourself: moving from doer to delegator, from “I did it” to “we built it.”

2) Internal CEO (Promotion)

You join early, grow with the business, lead major functions, then step into CEO when the board and team already trust your execution. Your advantage is context. Your risk is becoming too inside-the-boxso keep external perspective through mentors, customers, and market reality.

3) Hired CEO

You’re brought in to lead based on experience, reputation, and fit for the next stage. Your challenge is the learning curve and culture: you must earn trust fast, respect what exists, and still drive change.

CEO Mistakes You Can Avoid on Purpose

• Hiring too early: adding headcount before clarity creates expensive confusion.
• Being the hero: rescuing everything yourself trains the team to wait for rescues.
• Avoiding hard conversations: delays compound. Small problems become expensive problems.
• Confusing motion with progress: meetings are not momentum; outcomes are momentum.
• Letting the story drift: if you can’t explain the “why us” in one minute, the market won’t wait for minute two.

So… What Steps Did You Take? A CEO-Building Blueprint

If you want a clean checklist (you do), here’s a CEO-ready sequence you can actually execute:

1. Work near strong CEOs and watch real decisions, not highlight reels.
2. Manage people early and oftenhiring, feedback, delegation, culture.
3. Own a scoreboard (revenue, retention, growth, or product outcomes).
4. Learn capital and runwayfundraising, budgeting, and stakeholder communication.
5. Build go-to-market instincts by staying close to customers and deals.
6. Develop your psychology so you can lead when things get weird (they will).
7. Earn the CEO seat by doing the CEO work before you have the CEO title.

Becoming a CEO is rarely one dramatic moment. It’s usually a quiet accumulation of trust, judgment, and repsuntil one day the seat opens, and you’re the obvious choice. Not because you wanted it the most. Because you prepared the most.

of CEO Experiences (The Real Stuff, Told Straight)

Below are composite “field notes” drawn from common experiences CEOs and senior operators describeespecially in SaaS and venture-backed startups. No superhero myths. Just the real texture of the job.

1) The board meeting that rewired your brain.
You walk in with 27 slides. You walk out realizing you needed 5: the problem, the plan, the math, the risks, and the ask. A great board doesn’t want theater; it wants clarity. The best lesson is how quickly smart people spot fuzzy thinking. After a few rounds, you start building the company differentlybecause you know you’ll have to explain it. That pressure becomes a kind of leadership gym: uncomfortable, but transformative.

2) The first “real” hire that went wrong.
Everyone remembers the hire that looked perfect on paper and struggled in practice. Maybe they couldn’t execute without constant direction. Maybe they were brilliant but toxic. The moment you finally admit “this isn’t working” is painfuland oddly freeing. You learn a CEO truth: keeping the wrong person is not kindness. It’s a slow leak in team trust. After that, you get better at interviewing for values, problem-solving, and learning speednot just pedigree.

3) Fundraising as emotional endurance.
You start optimistic: “We’ll raise quickly.” Then you discover the hidden curriculum: narrative discipline, pipeline management, rejection resilience, and follow-up stamina. The experience teaches you how to sell without desperationhow to stay confident while absorbing “no” after “no.” The best founders treat it like a process: qualify investors, run a tight timeline, show momentum, and never confuse interest with commitment until the wire hits.

4) The day you realize culture is what you tolerate.
A small behavior repeats: a leader interrupts, a team ships sloppy work, a meeting starts late every time. You ignore it because you’re busy. Then you realize everyone noticedand your silence became policy. CEOs learn that culture isn’t posters or perks; it’s patterns. So you start doing the unsexy work: setting standards, reinforcing them publicly, and addressing issues quickly, calmly, and consistently.

5) The loneliness nobody warns you about.
There’s a strange moment where you can’t fully vent “up” (to investors), can’t vent “down” (to the team), and friends outside startups don’t speak the language. CEOs build peer circles for a reason. The best ones find truth-tellersother CEOs, mentors, or operatorsso they can process reality without destabilizing the company. It’s not weakness. It’s maintenance.

If you take anything from these experiences, let it be this: CEOs aren’t born with a special gene. They’re built through exposure, responsibility, and the willingness to keep learning after every messy week. The seat doesn’t require perfection. It requires ownership.