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How to Create Career Paths at a Small Startup

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

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. 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.

Today’s Advice Sponsored by Freshworks

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 out 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.

$10,000 for your customer acquisition? You got it.

What’s the number one reason startups fail to gain traction? Lack of customers. They are hard to find, hard to convince, and more discerning than ever. Does this sound like you? I’d wager $10,000 it does. Specific, repeatable efforts that drive new users is all an early-stage startup should be focused on. That is why it is incredibly important to have tools that make it possible.

Luckily, Freshworks’ FreshMarketer has every marketing tool you need. And, because we know that the "marketing learning curve” can make or break a business — we’ve selected a tool that is both easy to use at the earliest stages of business AND powerful enough to carry from learn, to grow, to scale. Think of it as a unicorn factory.

Here’s SOME of what you’ll get (seriously, it does more than this):

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  • CRM Integration (Once you’ve got them in the door - you need to treat them like royalty)

Freshworks and are partnering to give $10,000 to qualifying Startup companies to acquire and maintain customers for life using best in class platforms.

Don't let the cost and difficulty of marketing deter you. Freshworks has amazing customer marketing tools from first-touch-marketing to after-sales-retargeting. Take us up on this — we promise, you'll thank us later. Click here to get started.

PS check back in 2 weeks — we’ll be giving away access to a best in class CRM for all the customers you’ll acquire with FreshMarketer.


In Case You Missed It

How Do I Design My Startup Around My Life? There’s very little preventing us from designing our startups around our life goals. It starts with us being very clear about what we want to achieve and then taking clear, small steps toward those outcomes.

7 Habits Of Highly Successful Entrepreneurs From ice cream powerhouses to e-commerce pros, here are some traits from great founders that I’ve observed and tried to emulate throughout my 20-year career as an entrepreneur.

How Much Should I Be Working? (podcast) While there's truth to the assumption that more hours equal more growth, we'll explore how it benefits to think quality and not quantity when it comes to your weekly punch card.
Love this topic? Hate it? Let's chat on social media!

Wil Schroter
Founder & CEO @
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