🪜 Your Career Ladder Is a Lie (and That’s Okay)

A founder once asked me if I could build them a “robust career ladder” for their 43-person startup.

They were pre-Series B, had two people in Ops, and a team structure best described as “choose your own adventure.”

When I asked how roles were currently defined, they said, “Well… we kind of just figure it out as we go.”

Cool cool cool. Welcome to scaling, my favorite fever dream.

The myth of the early-stage career ladder

Let’s just say it: career ladders under 100–120 people are mostly decorative. Like those Pinterest-perfect home offices with zero visible wires. Technically achievable, but only if you don’t actually use them.

In theory, ladders are neat. Predictable. Fair. In practice? They’re a mismatched spreadsheet of levels and titles that no one follows, maintained by one increasingly desperate People person and reviewed once a year (if that).

Here’s why they don’t work:

• The work is too fluid.
  A PM today is designing onboarding flows, running standups, and writing copy. Tomorrow they’re moonlighting in sales. Roles stretch and morph faster than any static framework can keep up with.

• You don’t have enough layers (or people) to ladder.
  Career ladders assume a stable hierarchy: Associate → Manager → Director → VP. But if you’ve got a 12-person marketing team and one VP, you’re not building a ladder. You’re building a single tightrope.

• They signal false certainty.
  People start asking, “When do I go from L3 to L4?” which, in a startup, is often code for “When do I get paid more for doing the same ambiguous job with a different emoji in Slack?”

So what do you build instead?

Forget ladders. Focus on what actually fuels growth, retention, and performance in scaling teams:

1. Skill growth over title growth

Early on, job titles are cheap. What’s expensive is building real capability.

Swap rigid level definitions for skill maps. What does great look like in this role, right now? What’s the next useful skill they can learn? What does mastery look like in this context, not some hypothetical FAANG ladder?

Try this:
Create a progression map with 3–5 core skill areas for each role (e.g., technical depth, cross-functional influence, problem framing). Show how these evolve. Review every quarter with:

“What’s one skill to double down on? One to stretch into?”

2. Context + autonomy > clarity + control

People don’t leave startups because they didn’t get a new title. They leave because they don’t see how they’re growing or where they fit in the bigger picture.

Give people radical context: What’s the company trying to do? What bets are we making? What’s broken that they can help fix?

Then? Give them room to build.

Your job as a People leader is less “define the path” and more “make the terrain walkable.” Set guardrails. Offer coaching. Shine a light on what’s needed. But don’t try to pave every inch.

Try this:
Run a quarterly “role remix” session. Ask:

• What are you doing that feels energizing?

• What’s draining you?

• What bets is the company making, and where could you lean in?

Let roles evolve with the person and the company, not despite them.

3. Show your work (and the tradeoffs)

If you do need a loose leveling system—for compensation bands, hiring consistency, or equity planning—keep it lightweight and transparent.

Instead of pretending it's a crystal ball, treat it like a map:

• “Here’s how we think about impact and scope right now.”

• “Here’s where this role could grow, if the org grows with it.”

• “Here’s what we can support today—and what we can’t yet.”

People can handle ambiguity. What they hate is the feeling you’re hiding the ball.

The real goal: Create a system where people grow with the company

In startups, the best roles are often the ones people shape for themselves. They see a gap, lean in, and build something new.

Your job isn’t to predefine that journey—it’s to make sure the conditions exist for people to explore it:

• Clarity on what matters

• Support when they hit walls

• Recognition when they level up (even without the fancy title)

So let the ladder go.

Give them a compass instead.

💥 TL;DR
Forget formal ladders in early-stage orgs. Instead:
✅ Map skills, not levels
✅ Create space for roles to evolve
✅ Offer context, not control
✅ Keep comp frameworks lightweight and honest

Free downloadable career progression conversation template for scaling orgs that want to grow people without pretending they’re a bank here.

If you’re tired of maintaining a ladder no one climbs, send this to your CEO. Or your People team. Or just print it out and ceremonially set fire to your old leveling matrix.

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