The Playbook I Used To Double My Salary (Twice)

Maya Grossman
Aug 4
3 min read

I never set out to “make high six figures.”

But by 37, I had. And more importantly, I did it on my terms.

I think it’s partly because I didn’t follow a traditional path.

I didn’t get a good job, worked my way up, and waited to get noticed.

Instead, I made strategic decisions at every step of my career.

Sometimes that meant walking away from a good thing. Sometimes it meant betting on myself.

But every decision was part of a bigger plan.

Today, I want to reverse-engineer that journey, so you can see exactly how I doubled my salary twice, and how you can start thinking more strategically about your own career.

Step 1: I stopped confusing hard work with progress

At 27, I hit a wall.

I was exhausted, underpaid, and stuck in a job that didn’t excite me.

That’s when I asked myself:

If I keep doing what I’m doing… where will I be in 5 years?

The answer made me pivot because that future wasn’t exciting.

So I left my job as a travel agent (yep, that’s what I did for 7 years) and moved laterally into tech. Not for more money, but for more growth.

It was a strategic bet, and it paid off.

Step 2: I prioritized visibility, not just results

Once I got my foot in the door, I didn’t sit back and wait. After a short few months of acclimating to this new environment, I went into full “I’m going to crush this” mode.

Instead of just doing my job, I looked for bigger problems to solve so I could show up like a leader, before I had the title.

Funny thing is, when you look for problems, you usually find them. So when I showed my boss a blind spot and what we could do about it, he promoted me on the spot. There was no position before our conversation he created it for me.

That mindset got me promoted 3 times in 4 years.

I doubled my salary and became a Director by making myself too valuable to ignore.

(Note this didn’t happen because I said yes to everything and worked crazy hours (although I did work hard). It happened because I learned how to add more value.)

Step 3: I played the long game

I didn’t take the next job for the title. I took it for the leader.

In fact, I almost said no because the original job description felt “too junior”. But the friend who referred me, and every person who interviewed me, said I would be a fool to say no. They couldn’t stop praising the hiring manager and told me it would be the best decision I've ever made. They were right.

The job wasn’t perfect at first, but the manager was exceptional.

And that changed everything. I ended up reshaping the role into what the company needed and what I could do best.

In the process, I learned how to manage up, navigate politics, and operate at scale, all skills that made me VP-ready later on.

(I also negotiated the title after I shifted the work and got exactly what I asked for.)

Step 4: I didn’t wait for the “right” opportunity

When I moved to California, I lost my network.

No one knew who I was, and I kept getting passed over.

So I made a new plan. Instead of going after VP roles that required a strong reputation, I started consulting to build relationships and prove my value.

It wasn’t forever, but it gave me leverage. One of my clients was Google. That helped grow my network significantly.

And within a year, I landed a VP role at a $400M startup and earned the highest salary of my career.