Startup Careers: How to Create Career Paths at a Small Startup

“How does someone "grow" in an organization that may never surpass a dozen people? My team wants is always comparing their growth path at my startup versus a big company — how do I become a better alternative?”

September 9th, 2020   |    By: Wil Schroter    |    Tags: Recruiting

The old days of having to grow our staff by promoting them into a management pyramid are (thankfully) wasting away. Startups can do way more with fewer people, which means fewer management layers and more empowered staff.  

Yet, we're still stuck in the old thinking of "I can only progress if people are reporting to me." It's a dying notion, yet one we struggle with as startup Founders to replace. But we have to figure out how to recast the career paths of our teams if we're going to learn to work in a new world of smaller teams doing 10x more than they used to.

A startup is a company that's in the early stages of development, usually characterized by a small team, fast growth, and limited resources.

Most startups fail, but some create amazing and lasting value.

To do so, they need to be able to scale up quickly. This means being able to hire people with different skill sets who can work together effectively. Keeping that staff around is just as important, so creating career paths for them is worth the time it takes to make.

But what goes into this process? Let's dive in to find out.

Growth Needs to be Unpacked 

When our staff talks about growth, they are really talking about three things — money, recognition, and empowerment.  Money is easy — we can always pay more. Recognition is usually a title issue, which can always be changed, although obviously being "Senior Director of Marketing" feels silly when it's a department of one. And empowerment is about giving someone the agency to do things on their own, or the reward for their achievements.

Cash = Contribution

We need to align cash compensation to the actual contribution, not the title. Titles imply a level of contribution, but in a small startup we need to be more explicit — "The more impact you have, the more we can pay you." Our staff needs to know that their salary isn't capped because of a lack of reporting structure, but to be fair, it also isn't endless either.

Top tech jobs startup companies offer should consider the median salary as a minimum. But a lot can be negotiated in the early stages of a startup, including equity, vacation days, and other incentives to bring sought-out employees onto the team. But that leaves one question: where do we find them?

What are involved resources tech hubs?

Tech hubs connect business leaders, researchers, tech professionals, and more — and can be built anywhere since they are digital. This type of online community is to connect those searching for tech jobs with those looking to hire.

Involved resources tech hubs are one avenue to find startup jobs for an online community and are a better option than an open search join log.

Titles Reflect Skill, not Direct Reports

As we've seen with the evolution of top tech jobs, it's not just about building products. It's about building companies and teams.

This means that if you want to be successful in this new world of startups, you need to know how to build a company as much as you need to know how to build a product — and that includes creating a job title for each member of the team.

We have to be mindful that titles still do matter to folks, but those titles need to be a reflection of skill, not the number of direct reports. That means a designer should be able to rank up from Designer > Senior Designer > Art Director > Creative Director without a single direct report. It's also important for those folks to know they can likely get to those titles faster than they could in a larger company because they will be given more agency.

Career paths in tech companies or

Empowerment to Make Contributions

This brings us to empowerment. At its core, we all want to be given the empowerment to do more, and test our skills. In a small startup, we need to flaunt the fact that our team will get way more opportunities to branch out and take responsibility for more in a smaller environment.

When it comes to empowering our employees, this brings us to another important point: the role of senior management. At a large company, there are hundreds of people in senior management positions. This means they can delegate tasks down to their subordinates and trust them with decisions they would not have made themselves.

If you're working at a small startup, chances are you'll be one of those senior managers — if not the only one. You're going to have no choice but to empower your team members and let them make decisions on their own.

Of course, this isn't an excuse for making silly mistakes or doing subpar work. However, it does mean that you'll need to give your team members freedom so that they can learn how to make decisions without having someone else hold their hand through every step of the process.

That additional responsibility will hopefully lead to more contributions which will then lead to more cash. See how that all works?

A keyword search remote team for engineer finance hr might not be one of the best startup jobs at tech companies, but that's the point of creating career paths so there are options to grow

Any Company Can be Outgrown

This isn't to say that our team may have ambitions to actually be managers unto themselves — there's nothing wrong with that. Or they may look to a larger company to learn from more senior folks which are something we can't provide.

Our job as Founders is to provide the best possible environment for the things we can be great at — that's it. It's the job of our staff to figure out whether they want to trade endless flexibility in their days for being on the clock in an office from 9a-5p.  

As startups with smaller staffs, we have to lean in heavily on being the better alternative to a corporate career path, not a limitation of one.

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About the Author

Wil Schroter

Wil Schroter is the Founder + CEO @, a startup platform that includes BizplanClarity, Fundable, Launchrock, and Zirtual. He started his first company at age 19 which grew to over $700 million in billings within 5 years (despite his involvement). After that he launched 8 more companies, the last 3 venture backed, to refine his learning of what not to do. He's a seasoned expert at starting companies and a total amateur at everything else.

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