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

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 a 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.

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 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.

Titles Reflect Skill, not Direct Reports

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.

Empowerment to Make Contributions

Which 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 opportunity to branch our and take responsibility for more in a smaller environment. That additional responsibility will hopefully lead to more contributions which will then lead to more cash. See how that all works?

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 is 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 9-5.

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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