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Writer's pictureTeam UNDASHED

Consider these 5 Things Before Joining a Business as Employee #1



After having worked in some of the top global law firms, I craved autonomy, speed, and impact and dove head first into #entrepreneurship and working with #smallbusinesses.


Over the past years, I've spoken to lots of people who want to be an early employee of a startup or small biz and interviewed many applicants who left corporate but weren't prepared for the ambiguity and expectations that come with being employee no. 1 (or 2 or 3 or....).


Are you multi-passionate, have a bias for action, and want to accelerate your learning across functions and skills?


Check out this list and see if joining a small business, an early startup, or becoming an entrepreneur is the right move for you.




Out of the 32.5 million small businesses in the U.S., 23 million have fewer than 20 employees and approximately 92% are considered microbusinesses, defined as businesses with less than 10 employees.

If you're a scrappy generalist, crave autonomy and responsibility, and enjoy turning a business owner's vision into reality, you might be perfect as an (early) employee in a small business.

I became employee no.1 of such a business in 2020 and often get asked what I enjoyed about my role and what advice I would give to someone who's interested in joining a small business.

Here are the 5 things you should consider before applying to join a small business as a full-time employee:

1. Are you multi-passionate and multi-skilled (i.e. you're great at a lot of things and enjoy doing a variety of tasks)?


While most businesses have similar functions like HR/hiring, marketing, customer service, operations, etc., many small businesses don't have the resources to create entire departments to handle the tasks related to these functions.

As an employee of such a business, you're expected to work cross-functionally and jump in wherever needed to keep the business running like a well-oiled machine.

2. If you don't know how to do something, can you figure it out and get it done?


When you jump into working for a small business - whether it's an eCommerce store, a brick-and-mortar shop, or an agency, your onboarding may look a bit different than what you're used to if you're coming from a more corporate role.


Unlike large corporations that offer multi-day trainings on all of the processes and tools used and available, employees in most small businesses are expected to be scrappy, apply their knowledge from previous roles, utilize the free training resources offered by companies like HubSpot, Airtable, and Asana, and learn via YouTube or Google how to quickly become an effective team member.

3. Are you comfortable 'learning by doing'?


Have you ever created a landing page for a campaign including copy and visual, sourced manufacturers for a new product, or launched a podcast from scratch with no clear directions or a step-by-step guide?

If the thought of doing these things makes you queasy, you may not enjoy working in a small business. As the business owner's vision, goals, and objectives change, you're expected to adapt, work through ambiguity, and learn by doing while keeping the vision front and center in all decision-making.

4. Are you willing to take full ownership of your work, knowing that things probably won't get done if you're not doing them?

One advantage of a large team is that responsibilities can be shared amongst colleagues as needed and someone else can step in and help you complete your work.

In a small business, the motto 'all hands on deck' is 100% accurate. If you're tasked with managing a project, you're expected to take full ownership of the project, make the team aware of any blockers or bottlenecks, and complete all work in a timely and appropriate manner.

Don't want to do something? Well, it probably won't get done - yikes!

5. Can you apply any transferable skills from personal experience or previous roles to keep the business running smoothly?

You may be surprised to hear that I think people who have worked many odd jobs, reinvented themselves multiple times, and tried a bunch of things, often have the best transferable skills I've seen in applicants.

Ever worked in retail or the service industry? You're probably great at customer service, diffusing intense situations, and maintaining a certain standard of work.

Being able to apply your soft and hard skills from previous jobs, hobbies, and life experiences is one of the greatest assets a small business can benefit from.

Now consider, does the thought of working closely with a business owner to advance their mission and scale their business excite you?



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