SDR → AE → Mgr → VP. It wasn't what it looked like.
READ TIME: 4 MINUTES
In 2013, I got recruited to join ZocDoc as a Sales Manager. A scrappy startup in NYC that was just starting to scale.
I left my final round interview, a dinner with members of the leadership team, on such a high. The train ride back to DC felt electric.
Then the offer came in.
It was a pay cut.
I said yes anyway.
I packed my bags, sold my car, almost doubled my rent, cut my apartment size in half, and moved to New York City. The apartment had mice.
From the outside, it probably looked like a lateral move at best, Sales Manager to Sales Manager. But it didn't feel that way. It felt like exactly the right next step — a new city, a product in HealthTech starting to take off, and the chance to manage a team at a company I hadn't grown up in.
One of the Senior Leaders in my company at the time questioned my move. She told me it was a bad decision.
That experience taught me something I've carried ever since:
Your career is not a ladder. It's a jungle gym.
On paper, my path looks linear.
SDR → AE → Manager → VP
But when you look closer, it was anything but.
I moved from selling best-practice research to breaking into SaaS.
I managed teams across three completely different organizations in three different industries.
I was asked to step back from a VP role — and instead of chasing the same title somewhere else, I stayed. AE and SDR Manager. Glorified title. Smaller scope.
Then I was laid off. Twice. In 2023 and 2025.
The last one is what pushed me off the corporate ladder entirely.
What drove me through all of it wasn't the title or trajectory. It was three things: learning something new, the people and building something. Whether that was selling into a new industry, developing a new process, or growing a team from scratch — that's what kept me engaged. Sometimes money was the motivator. Sometimes I took a pay cut to get to the right opportunity.
The ladder didn't account for any of that.
Throughout my career, people have always come to me with the same question:
"What's the next step?"
At several companies, I built out the formal career path — SDR to AE to Senior AE to Enterprise AE, sometimes to Manager. The yellow brick road. Some people were looking for clarity on the path to follow. Some of them asked: "But is this actually the right path for me?"
That tension never went away.
Because the ladder creates the illusion that there's one right way to move forward. There isn't.
Some of the most rewarding transitions I've seen looked nothing like the traditional path:
Teacher → SDR or AE in EdTech
Solutions Engineer → AE
Supply chain expert → AE → SE → President
SDR → Marketing
AE → Customer Success
SDR → self-taught engineer (yes, he taught himself to code)
Ad Sales → SaaS Sales
These weren't detours. For the people who made them, they were exactly the right moves.
Here's what I've learned from watching hundreds of careers and living my own:
The most important question isn't "What's next on the ladder?"
It's "What do I actually want from this chapter of my career?"
When I was hiring, the candidates who stood out weren't the ones who had checked every box. They were the ones who could clearly articulate why they wanted the role and demonstrate the will to figure it out once they landed it.
You don't need a perfect résumé. You need relevant skills, honest self-awareness, and a clear sense of direction.
So stop climbing the ladder.
Swing across. Step sideways. Go up when it's right. Step back when it gives you something the next rung never would.
The right move is the one that fulfills your goals — not the one that looks best to everyone else.
Hit reply and tell me one of two things: a move you made that looked unconventional from the outside but was exactly right for you — or what transition you are navigating today. I read every response.
To clarity and confidence in your career path,
Amanda
See you next Sunday.
