It takes a certain type of personality to want to work at a startup — and the crucial qualities of startup employees you decide to hire.
When I was 26 years old, one of my closest friends and I decided we were going to start a company. He was still in the process of finishing his MBA. I had recently taken the leap from my job as a copywriter working in advertising. And every few weeks he would fly to Chicago (where I was based), or I would fly to Atlanta (where he was based), and we’d trade off sleeping on each other’s couches while brainstorming what our first step was going to be.
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We called it Digital Press.
Over the past two years of building this company, I’ve learned a thing or two about the qualities of startup employees you need to look for.
I’ll never forget the day we decided to make our first hire.
He was a freelance writer recommended to me by a friend — and we were in the market to start hiring writers and editors (to replace the jobs my co-founder, Drew, and I were performing ourselves). We asked him to meet us at Soho House in Chicago, ordered a bottle of red wine to share, and “interviewed” him by the pool on the roof. He was a fiction writer with a passion for fantasy and sci-fi (not business writing, which was what we needed), and we were young and inexperienced just hoping someone would trust us enough to follow our vision.
We hired him — and fired him two months later.
Over the next year, Digital Press grew from my co-founder and I to nearly 20 full-time employees, before going through another period of reassessing who we had on the team and why. Those first 12–18 months, we were hiring 1–2 full-time people every single month, month after month. We made some absolutely terrific hires. We made some mistakes. But overall we learned (and are continuing to learn) what qualities make a truly exceptional startup employee.
Here are 9 that come to mind:
1. A great startup employee has to thrive in “organized chaos”
This was a phrase a mentor of mine, a startup founder himself, used to say all the time. “You have to be OK with organized chaos.”
What that means is, you have to not expect things to always be set in stone. Obviously, the goal for the organization is to find these grooves and build processes and best practices that scale and age well. But the truth is, a startup is as fragile as a newborn baby. Some days, you wake up and realize, “What we’re building isn’t actually scalable. We need to change things now.” And the best startup employees not only understand this mentality, but they help you spot issues along the way — for the improvement of the whole.
2. A great startup employee looks for ways to help beyond their formal job responsibilities
When you’re building a company from scratch, there is a never-ending list of things that can be done.
On any given day, my To Do list ranges from “in the weeds” tasks like prospective client follow-ups, current client follow-ups, training new employees, putting events on the calendar, etc., all the way to trying to imagine where the business will be in 5 years and how we’re going to get there. And fluctuating between those two states is extremely mentally taxing.
Great startup employees realize they are building their “future role” at the company. So they take it upon themselves to not only get their own work done, and done exceptionally well, but find other ways to check things off the company’s To Do list and add exponential value.
For example, our second hire was an Account Managing Editor whose responsibilities included working with clients, outlining and editing pieces, etc. But when she was hired, we had close to no processes in place. Nothing was organized. Documents floated between people’s emails. And she took it upon herself to not only perform her own responsibilities but help us organize every single file and document within the company.
3. A great startup employee cares more about the team than their individual title
This was something my own mentor bashed into my brain — and I’m thankful he did.
“Your title doesn’t matter,” he’d say to me, over and over again. “What matters is your quality of work. What matters is what you bring to the table.” He’d go on to rant about how many people call themselves a “CEO” when, in reality, they run a blog or a Shopify store and their only employee is a virtual assistant — and he’d used that as an example of how little your title means in the grand scheme of things.
Great startup employees also have to understand and internalize this concept.
When you’re working at a startup, and you’re part of building something from scratch, your title will never be able to fully encompass all the different things you do (if you’re a high-performer, that is). If you try to come up with a title that is an umbrella to all the different hats you wear, your title won’t make sense (both internally and externally). But without some sort of title, it’s also difficult (internally and externally) for there to be clarity around your individual priorities.
The way I try to “lead by example” here is the fact that I don’t refer to my “title,” period.
I never say the phrase, “Because I’m the founder, that’s why.” I refuse to call myself a CEO (even though we have investors, a board, and over a dozen full-time employees) because I don’t believe that’s what matters. The only thing I care about is building the company, putting the team in a position to succeed, and continuing to move forward. Spending even an ounce of energy caring about my own “title” is a poor use of time — and my hope is that everyone else on the team internalizes this same “value-first” mentality.
4. A great startup employee takes chances, learns quickly, and isn’t afraid to break things along the way
Something else my mentor used to say to me was, “Cole, I’ll never be upset if you make a mistake. I’ll only be upset if you were too afraid to take a chance in the first place.”
Building a startup is hard because almost everything you do is the “first time.” You’re constantly in exploration mode — which means, you’re probably going to be fumbling in the dark for a while.
A great startup employee thrives in this sort of environment.
They take it upon themselves to do some exploring on their own. They bring new ideas to the table, and point out areas for improvement. They try things because they know they can. And most of all, they understand when things need to change at a moment’s notice.
5. A great startup employee has a sense of urgency
Building on the above, one of the most important qualities in a startup (and the people the company hires) is speed.
In startup land, a single day can feel like a month. A month can feel like a year. And a year can feel like an eternity. Which means, in order to continue moving forward and making progress in a meaningful direction, every single team member has to be willing to run and sprint with things as soon as they become a priority.
There isn’t time to wait a week. In many cases, “tomorrow” is too late.
The time is now.
6. A great startup employee doesn’t measure their value between the hours of 9 and 5
As a founder, I really work hard to honor people’s personal lives, their weekends, their evenings and their time outside of work.
However, I also have a certain expectation for the people who say they want to be part of building something from the ground up. And in order to be a valuable addition to a startup, you have to be OK with the fact that your day won’t always start right at 9 and end the moment the clock strikes 5. Some days will start early. Some days will go late. Some weekends, you’ll even want to get some work done yourself — so that you don’t have a crazy week ahead.
But this is the tradeoff to working for a big, established company, where your role might be more cut and dry. In a startup, you typically have more freedom, but you also have higher expectations to live up to. In our case, we’re a 100% remote company, so employees have the freedom to work from home (or travel and work from an Airbnb).
But with that freedom comes the expectation that you provide exponential value.
7. A great startup employee doesn’t see their role as a “job,” but as an opportunity to build a career
As a bootstrapped startup, you have to make decisions with minimal resources. And because you have minimal resources, that means you need to hire people who actually want to be part of the vision.
The biggest differentiator between high-performing startup employees and “everyone else” is the way they treat their role. Without fail, we’ve found that hires who treat their role as a job and nothing more are the ones who don’t end up lasting. Either they become unhappy, or it’s just abundantly clear that they aren’t someone worth investing time, energy, and resources into. People forget that when you work for a company, the company invests a lot of money into each and every employee. Tens of thousands of dollars (if not more). So if you have minimal resources, and the way you deploy those resources is what dictates success, then investing in the wrong employee can sometimes mean the difference between life and death.
Great startup employees don’t see their role as a “job.”
They see it as an opportunity to improve their skills, master their craft, and become a leader in their industry in some form or capacity.
8. A great startup employee doesn’t encourage drama or start conflict
When you’re building a startup, you run into all sorts of things you don’t expect — especially when it comes to “people.”
The unfortunate truth is that not everyone you hire is going to be the right cultural fit. Some will interview well, join the company, and then end up becoming a source of toxic energy. Others will appear shy in their interview but turn out to be absolute all stars. Often times, it’s difficult to know who is going to be the right fit before they walk through the door and start interacting with the team directly.
What’s important, though, is how long you let negativity and toxic behavior fester.
Great employees, at any size company, are relentlessly positive. Plain and simple. They understand things go awry. They know not every day is going to feel great. They can ride the ups and downs of the journey, keep themselves centered, and be a positive force to the team — not a negative one.
As a founder, then, it becomes your responsibility to not only hold yourself to this same standard (and higher), but to also keep a close eye on how your team continues to develop and grow together. Some people won’t be long-term fits. Others will only make it a few weeks before you realize you’ve made a mistake. What’s important is that you acknowledge these bad hires, get them out quickly, and move forward in the direction you know will be best for everyone.
9. A great startup employee is willing to sacrifice short-term rewards for the longer-term payoff
Building something great takes time.
If you want to be able to say you were “in on the ground floor” before the company reaches its first or second big mountain of success, then you need to realize that means building the floor, cleaning the floor, and helping lay the bricks on the building one by one by one.
Early-stage startup employees are a unique and impressive group. They’re exceedingly “intra-preneurial,” in the sense that while the original concept for the business might not have been “their idea,” they are willing to take a certain level of risk to help bring you idea to life. It’s amazing to hear people say, “I was the 8th employee at Uber,” or, “I was part of the original 20 at Facebook.” In society, these early employees are praised and idolized almost just as much as the founders.
If you want to be part of that group though, you have to really internalize that none of those early employees signed themselves up for a “job.” They believed in the vision. They wanted to be part of the building process. And they dedicated a significant amount of time and energy into bringing that vision to life.