Operations
In media, the hardest thing to build isn't your tech. It's loyalty.
By Dan Stofenmacher ยท
Why retention has become the real bottleneck in digital media, why it hits our industry harder than most, and why I still don't think anyone has fully solved it, including us.
People assume the hard part of what we do is technical. The syndication pipelines, the compliance layer, the production systems that move content at volume across a dozen platforms. Those are hard, and they're where most of the conversation goes. But the genuinely hardest part of running a media operation, the one I think about most and feel least certain about, is keeping the right people long enough for any of the rest to matter.
And the reason it's so hard isn't a failure of management technique. It's that something structural shifted in the relationship between people and the places they work, and a lot of operations are still pretending it didn't.
A generation ago, people stayed: they stayed twenty years at the same company, sometimes out of true attachment, often just out of comfort or because the salary worked and leaving felt like a lot of trouble. Loyalty was, to some degree, the default. You had to actively break it for someone to leave. That world is gone, and the operations that built their retention assumptions on it are losing their best people without fully understanding why.
Loyalty used to be the default you had to break. Now it's the exception you have to earn, over and over, against a market that assumes the opposite.
The mindset of the market changed, and the math changed with it.
The clearest way I can describe the shift is in the question people ask themselves about work. The old question was some version of what do I need to do to be secure, to earn well, to build a stable life. The new question is closer to what makes me feel good, what lets me grow, where do I actually want to spend my time. That's not a complaint about a softer generation, it's just a different value system, and it reorganizes everything about how you keep a team together.
Under the old question, a salary that worked was usually enough. Under the new one, a salary that works is the floor, not the offer. People will leave a job that pays them fairly if they don't feel they're growing, if they don't feel seen, if the place doesn't mean anything to them. And they won't wait the way they used to. Nobody is giving you ten years to show them a path anymore. If they don't see growth in a year or two, they start looking, even when the money is fine.
So the benefits that used to be how you competed, the vacations, the bonuses, the long weekends, and the after-work events, have moved from being a differentiator to being the price of entry. They are no longer able to win people over; they are exactly what you need to avoid being clearly behind. The actual competition for keeping good people now happens on a different and much harder setting, the one made of culture, belonging, and growth, and it doesn't respond to a line in a budget the way a raise does.
Why this hits media operations harder than most industries.
Every industry is dealing with some version of this, but it lands harder in media work, and the reason is the nature of the talent. In a lot of businesses, a departure is painful, but the replacement is findable because the role is somewhat standardized. In editorial and content operations, the talent is hyperspecific in a way that makes every loss expensive and slow to recover from.
The person who writes hard, data-driven news copy is not the person who writes comedy scripts for short video, who is not the person who can write about film with the particular register of nostalgia, who is not the person with the instinct for what will clear a compliance review. These aren't grades of the same skill, they're different skills that happen to share the word writer. When you lose the person who was genuinely excellent at one specific vertical, you can't patch the hole with whoever is available. You have to find another person with that same specific aptitude, which is rare, and then you have to give them time to develop the context that made the last person valuable. The cost of a single wrong departure in this kind of operation is measured in months, not weeks.
This is, honestly, a large part of why publisher operations come to a partner like us instead of just building the team themselves. From the outside it can look like the value is having a system and putting people into it, but it isn't. The value is the much harder, much less visible work of finding, evaluating, and keeping hyperspecific talent across many verticals at once. That right there is a full discipline of its own, and one most operations underestimate until they've tried to do it and watched it fall apart.
Losing a great editorial hire isn't losing a seat you can refill. It's losing a specific aptitude you now have to find again, and rebuild context around, while the work waits.
What we actually do, and the principle underneath it.
So what do you do about it? We try a lot of things, and I'll describe them, but the things matter less than the principle they come from, because a list of perks copied without the principle underneath just becomes more table stakes.
We try to remember each person as an individual rather than a resource, to celebrate what they accomplish, to reward the good work specifically rather than generally, and to actually be there when someone needs help, including the kind of help that has nothing to do with work. If someone is going through a hard time with their family, or needs support that isn't about a deadline, we try to show up for that, because the relationship isn't only transactional and pretending it is would be both cold and ineffective. In a business this digital and this distributed, we also push hard against the isolation, with in-person meetups, with spaces to actually talk, with monthly dynamics like having the team vote for the colleague who showed up best for everyone else.
But the principle that organizes all of it is something we repeat constantly: there is no ego here, and nothing is personal. When we give feedback, it's about that specific piece of work and how to make it better, never about the person. That single norm does more for retention than any benefit, because it makes the place safe to be wrong in. A writer who knows that a hard note is about the draft and not about their worth will take the note, grow from it, and stay. A writer who experiences every correction as a verdict on themselves will leave the first chance they get, no matter how good the vacation policy is.
Part of what lets this work, and I want to be measured about this because it's easy to oversell, is that we're founders who stay close. The operation didn't start as a cold corporate structure, it started as people building something, and we've worked to not become inaccessible as it grew. That closeness is a real advantage in a moment when people want to feel they belong somewhere human rather than somewhere faceless. But I'd be lying if I said it was the answer, because closeness has a limit, and it doesn't override everything else, as I'll get to in a moment.
The part nobody likes to admit: sometimes you do everything right and still lose.
Here's the thing most writing about culture leaves out, because it's not flattering and it doesn't sell a tidy lesson. You can do all of this, genuinely and well, and still lose people you wanted to keep.
We've had people who showed us, again and again, that they were loyal, who stayed through the rough patches that every agency has, who were there in the bad moments precisely because all the closeness and the care had built something real with them. And we've had people who were with us for two years leave for a marginally better offer somewhere else, without even giving us the chance to have the conversation. Not because we did something wrong, but because they simply didn't arrive with loyalty as part of how they operate, and there's a limit to how much of that you can manufacture from the outside.
That's the reality underneath all the culture work: some people bring loyalty with them and respond to being treated well by becoming more committed, not less. Others treat every job as a temporary position to be optimized and abandoned the moment a slightly better number appears, and no amount of belonging will change that, because the individualism is in them before they ever reach you. And the market has tilted toward the second type. More people now think the path to a good life is to look out for themselves first, to keep their options open, and to never get too attached. I understand the logic of it, even as I spend a lot of energy trying to pull the people around me out of that mindset, because I think it makes for worse work and, frankly, worse lives. But I don't pretend I win that one every time. I don't.
And closeness is not the same as softness.
Building a close-knit, human culture has a drawback that is rarely discussed: it can be mistaken for a lack of boundaries. If this is the case, it must be corrected immediately to prevent the entire thing from collapsing.
Not long ago I had to deal with someone on the team who was, to put it plainly, playing people against each other, telling different managers different things and trying to route around all of them to get to me, the way a kid who doesn't like mom's answer goes to ask dad. I had to be very clear with them, so I told them that yes, we're close, we're friendly, we're genuinely good to the people here. I know it can feel like we're all friends, but we are not friends in the way that word lets you off the hook. I'm your boss, and this is a serious place. I value transparency and good faith above most things, and I have no room for someone trying to game the closeness as if it were a weakness to take advantage of.
That's the part of culture that the optimistic version never mentions. A place where there's no ego and nothing is personal only works if the same place is willing to draw a hard line when someone confuses warmth for an absence of standards. The closeness and the boundaries aren't in tension, they're the same thing. You can only afford to be that human with people precisely because you're willing to be that clear when someone tries to take advantage of it. Take away the boundary and the warmth stops meaning anything, because it stops being safe for the people who are there in good faith.
A culture with no ego only survives if it's also a culture with a spine. Warmth without boundaries doesn't read as kindness; it reads as a thing to take advantage of.
You keep building it anyway.
I want to be honest about where this leaves things, because I don't have a clean ending for this one.
We work at this constantly, we reinvent the ways we try to keep good people, we put real effort and real care into building a place worth staying in, and we still lose some of the people we most wanted to keep, and we still have to draw hard lines with some of the people we were most generous with. That's not a failure of the approach, it's just what the work actually is right now. Loyalty stopped being something people bring and became something you have to build, person by person, knowing it won't always take.
If there's a conclusion, it's only this: in a business where the talent is this specific and this hard to replace, the operations that succeed aren't the ones with the best benefits, the kindest founders, or the smartest retention strategy. They are the ones who always show up for their people without any illusions, who stay close without becoming sentimental, and who accept that even if you do everything correctly, you may see someone leave for no reason at all. You keep building it anyway, and that's the job.
Milan Lab builds and operates editorial, content, and software teams for digital publishers and media companies. See how we work.