5 Tips for Hiring Your First Employee

now hiring sign

Moving from just yourself (or a group of founders) to hiring your first employee is filled with terror and peril. At UserScape, we’re fortunate that our first hire, Rebecca (our Happiness Engineer), has been with us over 5 years now. Actually, nobody has ever left UserScape, but that’s a post for another day!

As I look back on that initial hire and others we’ve made I think there are a few key things you need to consider when making your first hire, especially if you’re a bootstrapped company.

1. Hire for support first

If you’re in software, you probably already have some technical chops. If you’re growing, support is probably the pain point that’s making you consider a hire to begin with.

Hiring for support frees you up from the common support requests to continue development and sales on your product.

2. Hire from your customer base

This one is a little tricky; stealing your customers’ employees doesn’t always sit well with your customers! That said, this is a great route to go because you can find someone who already knows your product and really enjoys using it. It’s like they’ve been trying out for a job at your company the entire time!

In our case, Rebecca was leaving her old job and just sent us a résumé on a whim. It so happened her timing was perfect! Even if you don’t get that lucky, if you’ve established a bit of a community, make them aware of open positions. If there are some stars in the community already publicly helping out, don’t be afraid to reach out to them.

3. Hire for trust

Nothing is more important than trust in your early hires. Pass on that person who seems like a superstar but your gut tells you isn’t answering questions fully or truthfully.

This is why hiring from your customer base for early hires is so great. You’ve already been interacting with them and know them outside the context of a formal interview. You probably have a sense of their work ethic, their technical knowledge, and their personality.

In a very small business trusting your employees with money, access, and information is key to them being effective. If you have to hold all the keys you’re not really getting your money’s worth. In a remote business, you’re also trusting them to manage their time effectively.

You’re also probably pretty protective of your baby and are scared about letting in outsiders. Your mental health basically makes hiring for maximum trust a requirement.

This is why founders often hire from within circles of trust. However….

4. Don’t hire your friends

I’ve seen this go wrong more times than I can count. If you want to be friends with someone, they pretty much can’t work for you. It’s not impossible to make it work, but it’s awfully risky.

5. Talk to an accountant

Don’t skip this one. This is the most important step. There are loads, and I mean loads, of places you can go wrong when you get into withholdings, benefits, and taxes. We’ve made several of these mistakes even with accountants since day one.

If you’re hiring remote you’re in for a real treat; you’ll need to learn about nexus, registered agents, and registering with the secretary of state of the state your remote worker is in.

Dealing with all this is well beyond the scope of this post, but seriously: talk to an accountant before you make a hire. If you’re hiring remote don’t go with the local guy who does the deli’s taxes, either. You probably need a bigger local firm or a regional one that’s familiar with multi-state companies and ideally software as well.

Bonus: Hire part time? Outsource?

I’ve always been pretty set on hiring full-time employees. I think this is my own hangup though and you shouldn’t be encumbered by it!

Today, there are a lot of great ways to hire  part-time workers. Also, with the option of working remote it’s much easier to find people willing to put in 10–15 hours after their day job from their home. A part-time worker can be a great way to bridge the gap between your current needs and hiring full-time employees. It’s also  a lot less accounting work and less benefits cost.

Outsourcing your support can and does work for many people. In our case, I knew I had a full-time job to fill, and it was important to me to find somebody I could train and trust. Rebecca also helps with other things, like accounts receivable.

You probably know in your gut if your company is better off outsourcing for now, or if you’re ready to hire and grow. Hopefully these tips will help you make wise choices as you set about hiring your first employee. Just stay away from Rebecca, she’s ours.


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