It is a linear, predictable, and incredibly boring path. It also happens to be the slowest way to increase your salary and influence in the modern tech industry.
The most successful people I know in startups didn't climb a ladder. They climbed a Jungle Gym. They moved sideways, diagonally, backwards, and across entirely different disciplines. And in doing so, they built a rare stack of skills that made them untouchable.
The Problem with the Ladder
When you climb a traditional corporate ladder, you are competing against everyone else on that exact same ladder. If you want to be the VP of Engineering at a Fortune 500 company, you are competing against 10,000 other highly competent engineering directors.
You become a commodity. And commodities don't have leverage in salary negotiations.
Furthermore, the ladder is fragile. If AI suddenly automates 40% of standard front-end development, the people who only know how to climb the front-end ladder are going to fall hard.
The Power of the Jungle Gym (Skill Stacking)
The Jungle Gym strategy is based on the concept of "Skill Stacking" (popularized by Scott Adams). It is very difficult to become the top 1% in the world at one specific thing (e.g., being the best Python developer). But it is relatively easy to become the top 20% at three different things.
When you combine those three things, you create a unique intersection where you are the top 1%.
Consider these Jungle Gym career moves:
The Engineer -> Sales Engineer Pivot
You are an okay backend developer. You take a lateral move to become a Solutions/Sales Engineer. Suddenly, you are the only person in the sales department who can actually read the client's API logs. You start closing massive enterprise deals because clients trust you. Your compensation doubles because you are now tied to revenue.
The Customer Success -> Product Manager Pivot
You spend two years talking to angry customers on Zendesk. You know the product's flaws better than the CEO. You make a diagonal move into Associate Product Manager. While the other PMs are guessing what users want based on analytics, you know exactly what they want because you've absorbed 5,000 support tickets. You get promoted faster than anyone else.
The Big Tech -> Early Startup Pivot
You take a "step down" in title and a 20% pay cut to leave Google and join a Seed-stage startup as employee #4. You learn how to set up AWS from scratch, how to interview candidates, and how to talk to VCs. Three years later, you are a VP of Engineering, skipping five rungs of the traditional ladder.
How to navigate the Jungle Gym
If you want to break off the ladder, you have to get comfortable with short-term discomfort for long-term leverage.
1. Stop obsessing over titles.
Titles at startups are made up anyway. Focus entirely on scope and autonomy. I would rather be a "Product Specialist" who reports directly to the CEO than a "Senior Director of Product" who reports to a VP of a VP in a 10,000-person bureaucracy.
2. Follow the pain.
The easiest way to move diagonally is to find the thing your company is terrible at, and volunteer to fix it. If the engineering team is building great features but nobody is adopting them, volunteer to spend 20% of your time writing technical marketing content. You just built a new rung on your jungle gym.
3. Embrace the "Step Back."
Sometimes you have to take a lateral move or a slight pay cut to enter a new discipline. Do it. The compounding interest of a diverse skill set will pay off massively in your 30s and 40s.
The ladder is crowded, stressful, and fragile. The jungle gym is fun, chaotic, and ultimately, much more profitable.
