3 Essential Tips For Hiring Freelancers With Your Startup

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Hiring freelancers for your startup: it’s something everyone struggles with. There are roughly a trillion copywriters out there, Facebook advertisers, front-end developers, social media managers. And while the gig economy makes it easy to find these kinds of professionals, sifting through the incredible amount of resumes and portfolio sites that basically all look the same to you can be an overwhelming experience.

Here are a few tips to make it easier.

Know where to look for freelancers

Ok, so in the situation that you’re not as fancy as I assumed above or your network doesn’t have anyone to recommend that you really dig, the next step is to know where to look for a good freelancer. Try these spots:

  1. Chances are that if you need to hire a freelancer, you run in circles with other entrepreneurs who also hire freelancers. Use those connections to your advantage! Whether it’s a LinkedIn post to your network or a private message to a close friend on Facebook, ask them if they have any recommendations of people for you to work with. This is like asking to speak to someone’s reference before they’ve even applied for the job. Bonus: they might also be able to tell you of some people you should definitely stay away from. Bottom line: you’re a big deal. You know people. Use those contacts, my friend.

  2. I definitely suggest Upwork as a starting point. It’s a great marketplace to find skilled individuals, but beware, it’s not as great for freelancers as it is for business owners.  Freelancers are getting nailed with fees and face high competition from countries all over the world where the cost of living is lower—making it really hard to compete and still make a living wage. If you want to hire someone in a first world country, expect to pay first world prices. Spend some time with their portfolios, reading their articles, etc. The best thing you can do for yourself is learn a bunch about them, then ask some thoughtful and individualized interview questions which will really help you narrow down the talent pool.

  3. Start attending your local Chamber of Commerce meetings. The gig economy affects us all, and the more ambitious freelancers aren’t waiting by their computers for job offers to come through—they’re out in the community making things happen for themselves. If you don’t come across a great freelancer after a meeting or two, ask come of your new contacts who they have used and you’ll likely meet some great local talent.

Make all communications clear

This is a very important tip, and I can tell you from personal experience, it’s always best to take the terms of your agreement with a freelancer clear. Put it in writing if you can.

Everything from deadlines to design expectations to word count. You have to remember that they are not your employee; you’re not working with someone who shows up to your office every day and can recite the company mantra. You have to assume that your freelancer has a fuzzy understanding—at best—of what you need. Never assume anything. Make your communications very clear so you both come out of the working relationship feeling satisfied.

Document everything

It doesn’t happen very often, but there are people who take advantage of this whole gig economy thing. Don’t allow someone to take your money and run…. Have the freelancer sign a  formal contract—even for small projects so you’re covered in any circumstance. Use a time tracking software like Toggl so you can see how they’re spending their time. Save Paypal receipts.

Like I said, most freelancers are looking to build their portfolio and their reputations. They only want to do good work for you; but in the case that you hired a bad egg, being prepared with documentation will make it easier for you to handle a bad situation.


Hiring a freelancer can be scary, but it’s a super affordable way to offload tasks in your business that you don’t have the skill or the time for. And for bonus points, you’re supporting a small business owner and keeping the creative economy moving. So are you ready? Go hire that first freelancer with these essential tips.


Meet the Author: Shauna Armitage

Shauna is a Marketing Director or Fractional CMO helping early-stage startups scale with effective strategies, creative solutions, and unparalleled integrity by making the most of small budgets for maximum impact.

As a vocal advocate for women in business, Shauna is on a mission to redefine what it looks like to be a working woman and to support other women doing the same. She spends her free time traveling with her husband and four kids while drinking Coca-Colas. Connect with her on Instagram at @shauna.armitage.

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