How I Hired Freelancers at LinkedIn

So you’re getting ready to launch a freelance design career. Your eye is honed. Your skills are sharp. Your portfolio is gorgeous.

There’s just one problem: How do you go from great design to great design that you get paid for?

The answer is to understand the person doing the paying – i.e., your future client.

To provide insight into how clients think, let me give you a glimpse into how I hired freelance designers as a marketing manager at LinkedIn. That way, you’ll know exactly who your audience is – and how you can win their business.


The Need

The first thing to understand is why a client is hiring a freelance designer in the first place. There are two basic scenarios:

  1. The client is from a tiny organization. Let’s say that your client works for a 5-person startup or a small nonprofit. In this case, it’s unlikely that his/her organization has a full-time designer on staff. And as such, he/she is looking for a freelancer who can get work done for less than the expense of hiring someone full-time. In this case, the need is focused on cost.

  2. The client is from a larger organization. In the other scenario, your client works for a bigger firm – anywhere from a 50-person established business to a 100,000-employee multinational. Now, you can be fairly certain that any organization of this size has at least one full-time designer on staff. So why is the client hiring a freelancer? Given that the “price” of using an internal designer is essentially $0 as far as the client is concerned, cost isn’t a likely motivator to go freelance. Instead it’s much more likely that the client is looking externally because their internal design team is stretched too thin and so his/her project has been backlogged for weeks. And hence, the need in this scenario is actually focused on speed.

This second scenario was absolutely the one I found myself in at LinkedIn. Even though our internal design team was awesome, that same awesomeness ensured that they were always overwhelmed by the demands on their time. And so when this resource crunch got particularly bad, I would look for external design support as a way to get my projects completed faster.


The Search

Now that you understand why a client might search for freelance designers, let’s talk about where they’ll search.

The first thing to appreciate about this search is that the internal designer isn’t the only busy person at the client’s company. The client is just as busy, too.

Because whether they work for a tiny organization and have to juggle multiple roles (e.g., they’re doing marketing and sales), or whether they work at a larger organization and are rushing to get a project done (given that they couldn’t wait around for their internal designer in the first place), the client’s time isn’t unlimited. Which means they certainly don’t have unlimited time to spend on this search.

And so, even with the rise of freelance sites like Upwork, clients would prefer not to spend hours sorting through hundreds of proposals. Instead, they’d much prefer to go with a designer who’s already been vetted and is ready to go.

And this desire leads them to get recommendations from their friends and colleagues. For example, at LinkedIn, once a freelance designer completed a project successfully for one of my colleagues, she became the go-to freelancer for every single marketer on my 30-person team. That’s how powerful reputation and trust is in the designer selection process.


The Bid

We’ve covered why a client wants to hire a freelance designer and where they look. Now let’s look at who they ultimately pick.

To illustrate, let’s go back to my experience at LinkedIn. Again, my need for a freelance designer was based primarily on speed. And because I was looking to move quickly, I didn’t want to sort through a bunch of different designers – instead, I just got a few recommendations from my colleagues.

Now, amongst these handful of options, how did I make my final pick?

First, I looked at their portfolios. Not to see who had the best designs, mind you – but to screen out those that weren’t adequate.

Wait a second - why wasn’t I focused on finding the best designer? Wouldn’t it make sense that the best designer would win???

Not necessarily. Go back and remind yourself about my particular need. Was it to get the absolute best design? Nope. If that were true, I would have waited around to use our rockstar internal design team.

Instead, my true need was focused on speed. Because at the end of the day, my performance as a marketer would be judged most harshly on whether I launched my campaign on-time – and only secondarily on quality. After all, a decent on-time project beats a beautiful project that’s stuck on the drawing board in just about any scenario.

And so when I looked at portfolios, I knew that I couldn’t afford to eliminate good designers just because they weren’t the best. Indeed, what if the very best designer turned out to be a perfectionist diva who missed all my deadlines? And hence, I only removed completely unacceptable quality work from consideration.

Left with just three final options, I turned back to the real need: Speed. And so I asked the designers to give me bids and estimated timelines for completion. Here’s an approximation of what I got in return:


  • Designer A: 4 weeks, $4,000

  • Designer B: 2 weeks, $6,000

  • Designer C: 4 weeks, $6,000 – and we’ll do some extra work to make this project even better!


To simplify, here’s what each designer was really saying:


  • Designer A: I compete on cost

  • Designer B: I compete on speed

  • Designer C: I compete on quality


And so who do you think got my business?

Exactly. Designer B not only understood where I was looking by getting a great recommendation from a colleague, she also understood why I was looking by focusing her bid on my most important need. And that’s precisely why she ended up being who I was looking for.


Your Turn

OK, so now that you understand the client mindset, how can you leverage that understanding to win clients for your own freelance business?

There are just three steps:


Step 1: Get on the Radar

As discussed above, clients would much prefer to hire designers based on a simple recommendation than an exhaustive search process. So the first key step is to get onto that recommendation list. Here’s exactly how to do so:


  • Import your email address book into LinkedIn to make sure you have visibility into the careers of everyone you know.

  • Run a LinkedIn search for “marketing” and limit it to 1st degree connections – this will show you all the professionals you know in this space.

  • Send them each a message along the lines of:

“Given your marketing work, just wanted to let you know that I’ve recently started a freelance design firm. If you or your colleagues are ever in need of (low-cost/quick-turnaround) design work, please don’t hesitate to let me know!”

Note that you’ll want to focus either on cost or speed, depending on the size of the organization. That way you’re speaking their language!


Step 2: Get the Business

Based on your initial outreach, you’ll now start to be included in opportunities that were previously invisible to you. And if you’re not getting enough requests for bids, be sure to follow-up with your contacts. It may take a couple of messages to fully cement the connection between your new business and their needs – so be persistent!

That said, once an opportunity comes your way, go back to the question of “Why?” As in, why is this potential client reaching out for design support? Is it because she can’t afford to do the design in-house? Or because her in-house team can’t do it fast enough? The size of her organization should be an important clue but, when in doubt, don’t hesitate to ask: “What’s the number one thing that will make this project a success?” Too few designers, in my experience, ever try to understand what the client’s priorities are, which means they’re flying blind when it comes time to bid.

And then, when you do make your bid, hone it around what matters most – usually by cutting out nice-to-haves to keep costs down or increase speed. As tempting as it may be to focus on out-designing the competition, remember that your prospective client has a business goal to achieve that may not rely upon maximizing design quality. So the more you can focus on that business goal, the more you can do to win her business.


Step 3: Get More Business

Congrats! You just landed your first freelance design contract. You’re all set, right?

Not exactly. Because, presumably, the reason you started freelancing in the first place is to spend time designing, not trying to win design business. And wouldn’t it be nice if you didn’t have to work as hard for all of your future contracts?

In order to get to this point of a self-perpetuating freelance business (i.e., more designing, less selling), you’ll want to kick butt on your first project. Even if it means working overtime or delivering more than you promised, make sure that you blow it out of the water. And then, once your first client is overjoyed with your work, send her the following:


“Thanks so much for the opportunity to work on this project! I really enjoyed the chance to develop something both beautiful and (cost-effective/fast-paced) for you.

That said, since I’m just starting out as a freelance designer, would you mind sharing the project with your colleagues? If there’s anyone else on your team looking for similar work, I’d love to help out!”


This way, your awesome start doesn’t end up in a dead-end, but instead is shared widely with your next set of potential clients. And if you consistently do this kind of follow-up after each project, before you know it, you’ll be the de facto designer at organizations big and small. Which means more design work and revenue for you – all with less hassle.


Know Thy Audience

So there you go, the three steps from freelance newbie to freelance freedom – to the life and career that you want to lead. And while it’s undeniable that design skill will be critical to your success, empathy for your audience will be just as important.

So as you go forth and build connections with potential clients, deliver great results, and get referrals far and wide, never forget that great design starts with great understanding!

Upwork Note: Freelancers are now charged anywhere from $0.15 and $0.90 to submit a job proposal. To help freelancers and employers with this change, here is a comprehensive guide to the Upwork Connects pricing program with everything you need to know.