My first month at Fleet: the onboarding paradox

October 15, 2025 • 1322 words • 6 min read

🏷️ fleet work company culture workplace values

One month in, and I’m discovering something frustrating: onboarding at a place you’re excited about is harder than onboarding at a place you’re indifferent about.

When you don’t care that much, you can sit back and let the process wash over you. When you’re genuinely excited? Every day you spend reading documentation instead of helping customers feels like a day you’re not contributing. Everyone warned me this would happen. They were right.

The deep end comes early

A few weeks in, several members of the support team were out. I had to jump into the support queue earlier than planned.

The first couple days, a seasoned CSE worked alongside me. I handled triage and kept smaller issues from becoming distractions while they tackled the complex stuff. Then one day, I was the only CSE available.

It was a little scary. But I got through it without any major incidents, and I learned more in those few days than I had in the previous two weeks of reading. There’s something about real customer problems that makes the product documentation click in a way that studying alone never does.

The problem? Getting a taste of the action and then going back to onboarding made staying patient even harder. It’s like learning to ride a bike by reading the manual, then getting one glorious ride down a hill, and going back to the manual. You remember what it felt like to actually move.

CEO shadow: not what I expected

Fleet has a three-day CEO shadow program for all new hires. I thought it would be boring. Sitting in meetings all day, not contributing, just observing.

I was completely wrong.

I got to provide input as a seasoned client platform engineer, a former employee of a leading MDM company, and a former Fleet customer. In meetings full of people who’ve never been in those roles, I could advocate for customer viewpoints. I contributed to strategy around Fleet’s presence at JNUC. I didn’t want the three days to end.

If my full-time job could be following Mike around adding context from the perspective of a former CPE, manager, and customer, I’d jump at it.

What struck me most was how much my past experience mattered. Not just the technical knowledge, but the lived reality of being on the other side. That perspective has value, even when you’re brand new. Maybe especially when you’re brand new.

The customer sophistication gap

Fleet’s customers are smart. Really smart. Many of them are doing advanced work that pushes the product in interesting directions.

I’ve spent hours watching past customer training sessions and shadowing calls. The technical sophistication is higher than I expected. I need to step up my game to match their level, and that’s both intimidating and motivating.

The bar is high. That’s a good thing. It means I won’t plateau. There’s always going to be a customer doing something I haven’t thought of, asking a question that makes me dig deeper. That’s the kind of challenge that keeps work interesting.

Building while learning

Even while onboarding, I’ve been working on a Fleet AutoPkg processor and opening feature requests that came out of that work (#34137, #32965).

This is the onboarding paradox in action. I want to contribute. I have ideas. But I also need to trust the process and build the foundation that’ll make me effective long-term.

Empathy, still

My back injury recovery continues, and the flexibility hasn’t wavered. People don’t bat an eye when I’m camera-off because I’m working from bed at an unflattering angle. They’ve been flexible about doctor’s appointments. When I needed a day off for a minor outpatient procedure, I got it with no questions asked.

Everyone keeps telling me to prioritize my health over the job. Empathy being first in Fleet’s company values isn’t just words. It’s how people operate every day.

The inbox that stays empty

One month in, and I haven’t received a single email from anyone at Fleet. Not one email sent just to me, and not a single company-wide email either.

Everything lives in public Slack channels. Things that are important and permanent go in the handbook. Even customer communications happen through Slack whenever possible. This means everyone can see what’s going on, and anyone can contribute. It also means I have one less thing to remember to check, which helps me stay focused. Less toggling between tools wondering if I missed something important. No more searching through email threads to find context. Everything is where it should be, when I need it.

I knew this going in. It’s right there in the handbook. But knowing it and living it are different things. At most companies, there’s the way things are supposed to work according to the handbook, and then there’s the way people actually work. The gap between theory and practice is usually wide enough to drive a truck through.

Not here. The handbook says no email, and there’s actually no email. It’s refreshing to see that kind of alignment between what’s written down and what happens day to day.

The burnout I didn’t know I had

Here’s something I didn’t expect: it’s been easier to show up and be excited every day than I thought it would be.

I was dealing with serious burnout from my last job. I’d forgotten how much I love working not just with technology, but with people who love working with technology. I’m excited about my work in a way I haven’t been for a long time.

That energy makes the waiting harder, but it’s also a reminder that I made the right choice.

What’s next

I have an assignment coming up to help with Fleet’s first MDM migration for a customer. I can’t wait to get hands-on.

I can see what my role could look like in 6–12 months. I can see what the future of the product looks like. I want to get there now. I have a lot of ideas, and I need to figure out how to prioritize them, who to talk to, and when the time is right.

Moving fast is my default. Learning to move fast with other people is the challenge.

If I could tell week-one me anything, it’d be this: be patient. Pace yourself. Listen when people say onboarding will feel like it’s taking forever. Trust the process.

I’m trying. It’s just hard when you’re this excited to get started.

The real lesson

Here’s what I’m learning: the impatience I feel isn’t a bug. It’s a feature.

At my last job, I started out feeling exactly like this. Excited, eager to contribute, ready to move fast. And I never actually lost that. Even at the end, I still cared deeply about my team and making things the best they could be. I was still working hard, still trying to move fast.

But the context had shifted. I was moving fast to survive. To prove I was worth keeping around. To make myself indispensable so I’d have some control over my circumstances. That kind of speed is unsustainable because it’s fueled by fear.

Now, I’m moving fast because I’m excited. Because I see possibilities and I want to explore them. Because I’m working with people who are also excited, and that energy is contagious. That’s a different kind of fuel entirely.

The trick is learning to channel that excitement in a way that’s sustainable. To build the foundation even when I want to skip to the finish line. To remember that the point isn’t just to move fast, but to move well.

Month one taught me I still have a lot to learn about patience. But it also taught me that impatience driven by excitement is a much better problem to have than impatience driven by trying to hold together something that’s falling apart.

I’ll take this problem any day.