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For a long time, the fastest way to get a raise was to quit. Companies built that system. Now they’re surprised by the behavior it created. The truth is that when strong employees quit, they usually cite the same reason. It’s not because of the pay, but because they couldn’t see a path forward.
When I was building Prepory, I couldn’t afford to be one of those companies. Running a non-venture-backed startup, I couldn’t offer luxurious office perks, signing bonuses or stock options. What I had was a clear answer to one question every good hire eventually asks: Where does this go for me?
Today, Prepory has a team of nearly 100 people and an all-time high employee retention. This isn’t an accident. It’s what happens when you stop trying to make people comfortable and start giving them something worth staying for.
I’ve spent years building a team and working with thousands of young people entering the workforce. I’ve watched Gen Z get blamed for a retention crisis that was already here before they arrived. They’re called disloyal, entitled and impossible to hold of. I think that’s mostly wrong, and I think leaders who believe it are going to keep losing their best people.
I grew up watching the 2008 financial crisis impact my parents and many of their friends. Good people with decades of experience found themselves unemployed with no warning. Gen Z watched versions of that same story play out in their own homes. Many entered the workforce during or right before the pandemic. They’ve seen “family culture” language dropped mid-layoff announcement. Their skepticism isn’t a character flaw, but showcases their ability to read a situation clearly and act on what’s true rather than what they’re told. Companies shouldn’t ask for critical thinkers and then be surprised when those thinkers think critically about their own careers.
The companies I respect most have stopped asking how to make Gen Z more loyal and instead are asking whether they’ve given them a rational reason to stay. That’s a better question, and it leads somewhere.
Most people don’t leave bad companies — they leave unclear ones
What I’ve noticed building a team from scratch is simple. When someone joins and can’t see where they’re going, they start looking for a place where they can. That reaction usually says more about the clarity of the opportunity than the loyalty of the employee.
People who joined Prepory in our early days weren’t staying for comfort. They were staying because the work meant something and because they could see what their contribution was building.
Today, every member of our leadership team started in an entry-level role. That wasn’t a planned talking point. It’s what happens when growth paths are real, not something you just say in an interview.
Take our current Program Director. She started as a 1099 contractor with no guarantees and no full-time offer on the table. She did great work, moved into a W-2 role, then became a team lead, then a program manager and today leads a team of 70 employees.
Her story isn’t an outlier. It’s the model, and it continues to shape how we operate. Someone three weeks into their first role should feel just as comfortable bringing an idea to the table as I do as CEO. When people believe that, they invest differently in their work.
It’s also why we don’t hire externally for leadership roles. Every managerial position at Prepory is reserved for internal candidates. If you come here and do the work, the path is real.
We do offer perks like free lunches, team activities and flexible PTO. But those don’t answer the question employees are actually asking. The question isn’t, “Is this a nice place to work?” It’s, “Can I grow here?”
When that second answer is unclear, the first one matters a lot less.
What retention actually requires
The retention conversation in most companies focuses on what can be added: better benefits, stronger onboarding or a nicer office. These signal investment without requiring a harder conversation.
The more useful approach is removing ambiguity. Can your people see where they’re going? Do they know how they’re being evaluated? Do they believe staying is worth it?
A simple test: ask three people on your team what they need to do to get promoted. If you get three different answers, or no answer at all, you have a clarity problem, not a loyalty problem. And no perk or salary can compensate for what is ultimately a dead-end role.
High performers, especially younger ones, have little tolerance for institutional vagueness. And vagueness often signals that the real answers aren’t the ones the company wants to say out loud.
At Prepory, we try to make this concrete. Every team member has a defined growth path, but more importantly, they help shape it. We do this through a simple quarterly conversation, separate from performance reviews, where each person identifies one skill they want to build and one problem they want to own. That input helps define their next few months.
We also encourage people to explore beyond their current role or even their current team. Employees move across functions, take on new challenges and build entirely different skill sets without leaving the company. The goal is for every person to feel like an architect of their own future, not a passenger in someone else’s plan.
That’s how we ended up with our first software engineer. One of our part-time coaches, who had a background in computer science, kept bringing forward ideas and projects he wanted to take on. We listened. Over time, those conversations evolved into a role the company had never had before.
He went on to lead the development of Rory, our college admissions AI tool, and most recently GradBloom, our in-house learning management system designed to make session notes, student data and application tracking more intuitive for our team. None of that was in a job description when he joined. It happened because he was encouraged to say what he wanted to build and we took it seriously.
The leaders who do this well aren’t doing anything complicated. They make the path forward clear. They give people real ownership and room to lead. They measure performance transparently and talk about it directly. They build roles that develop people, not just fill seats.
None of this is revolutionary, but it requires a level of intentionality most companies skip because it’s harder than ordering better snacks.
Loyalty has to be earned now — that’s a good thing
Loyalty isn’t gone. I see it all the time, in my own team and in the young people I’ve worked with over the years. But it’s important to remember it’s no longer a given. It has to be earned structurally, through how roles are designed, how growth is communicated and how much autonomy people actually have.
Ultimately, this is a good thing. It means the companies willing to do the work will build teams that are harder to poach, more engaged and more invested in outcomes. Gen Z isn’t the problem — they’re just watching closely. If you think about it, it is exactly what you want in a high performer.
For a long time, the fastest way to get a raise was to quit. Companies built that system. Now they’re surprised by the behavior it created. The truth is that when strong employees quit, they usually cite the same reason. It’s not because of the pay, but because they couldn’t see a path forward.
When I was building Prepory, I couldn’t afford to be one of those companies. Running a non-venture-backed startup, I couldn’t offer luxurious office perks, signing bonuses or stock options. What I had was a clear answer to one question every good hire eventually asks: Where does this go for me?
Today, Prepory has a team of nearly 100 people and an all-time high employee retention. This isn’t an accident. It’s what happens when you stop trying to make people comfortable and start giving them something worth staying for.
