Here’s a thing that happens: sometimes early-stage entrepreneurs find themselves light in the old wallet and needing to make some side cash while growing their startups. That’s been me at several points in my career, including recently. So, in true ego-centric marketer fashion, I figured why not combine my consulting efforts with a new experiment that builds upon the most-read blog post I’ve ever written? And so, our hero embarks upon a new journey into the depths of the freelance hell known to many as Upwork.

That post was a Medium piece, How I’m Gaming Elance & Guru, that covered “growth hacks” I used a few years ago to get more – and better – clients on the two freelance gig sites. The biggest game changer move was to shoot a personalized video for each project I applied to, immediately setting myself apart from every other freelancer. This all worked pretty damn well. Then I got busy and didn’t use the sites for a while.

Since then, Elance and Odesk merged to form Upwork, and I found myself curious about the new site, how it worked, what I could do to game the system again, and wanting to test the waters to make some quick money.

DOES UPWORK SUCK?

People hate Upwork. I get that, I really do. Generally speaking, gig marketplaces that connect job providers with freelancers like this often result in a situation where the lowest bidder wins out. Upwork (and similar sites) are filled with overseas workers willing to complete jobs for pennies on the dollar. On top of that, clients on gig sites are known to have ridiculous expectations for the money they are offering, creating a shitty environment for all parties involved.

But that’s the common way to view Upwork and I’m not interested in that crap. What I am interested in, is how I can work the system to my benefit, mainly defined by:

• High quality clients
• Strategy jobs with no-to-little execution
• Reasonable fees
• Minimal pitching/applying time

I might need to swim through a river of shit to get to the good stuff, but my theory was that I’d eventually be able to spot quality clients for whom I can have a real impact while earning good money. I wanted to find patterns for identifying these clients, pitching them, and closing jobs. Finally, I wanted to explore using Upwork as a lead generation tool, not just a site where you apply for specific jobs posted.

THE SET UP

Since I’ve had experience on sites like Upwork, I already knew a few ways to maneuver the search process. Three key filters on Upwork are Job Type, Experience Level, and Client History.

An easy filter is Job Type, for which I exclusively choose fixed price. No way in hell am I getting into a situation where I have to track and report hours for a damn freelance gig. For Experience Level, I typically avoid Entry Level because, well, those guys can’t afford me. While Expert is ideal, I’d venture to say most jobs are tagged Intermediate, so that’s a good place to be. Finally, I don’t get too picky with Client History because a first-timer isn’t necessarily a bad thing. Just consider that when reviewing job posts, but don’t rule those folks out.

When looking at job categories, I never did determine a fool-proof way to pull out only the right kind of gigs. Take these “marketing strategy” posts for example:

I don’t know about you, but running someone’s social media accounts isn’t what I think of when I say “marketing strategy.” End of the day, you just need to learn how to spot bullshit jobs from their titles and move on quickly.

90 UPWORK APPLICATIONS

All in, I applied for about 90 gigs on Upwork in the span of a few months. My go-to approach from Day One was to go HAM on the customized videos and use those to razzle dazzle all potential employers. The videos were a great concept because they: demonstrated I was English speaking, showcased my personality, brought life to my application, and (presumably) pleasantly surprised the application reviewers. The downside, however, was the time and effort involved in creating them.

Then, like a true growth hakkerz, I questioned the validity of this approach after all these years and threw in two new experimental moves – no videos / all text pitches, and what I call a “creative” pitch, which involved me outlining 6 reasons the hirer should pay attention to me in an unconventional format (that included a little humor).

Beyond gigs I proactively found and applied to, I was also invited to apply for six jobs. Immediately after you post a project on Upwork as a job provider, the system recommends best-fit freelancers you can easily invite. For the invites, I skipped the flashy pitch and instead provided clear lists of my experience.

WINS & LOSSES

Out of those ~100 gigs (90 applications + 6 invites), I converted 23 of them into potential wins. Why “potential” wins? Well, seven jobs that were offered to me I decided to pass on for a number of reasons, the primary ones being red flags popping up during communication with job owners and/or too much execution involved. As of today, I have 12 job applications that are still “TBD” status, which means I’m in active conversations with the job owners, but haven’t closed or lost them yet.
So I’m working with an approximate 24% close rate, if you include the “Pass” jobs. But that’s not what I care about for this experiment. I’m more interested in the micro numbers specific to how each job was pitched.

Obviously this isn’t a statistically significant experiment, as I used the “video” pitch for way more applications than any other approach. But, hey, I’m no scientist. All that aside, here’s what the same chart above looks like when converted into percentages of wins/losses/passes/TBDs for each type of pitch.

Over time, my kick-ass personalized video pitches seemed to lose effectiveness, as win rates decreased. That’s when I tried out no videos and the “creative” pitch format. What jumps out at me, when analyzing the chart above, are three things:

I essentially won over 66% of the jobs I pitched using the creative format. And while I won almost 30% of the jobs I was invited to, that wasn’t really a surprise, given that the job owner sought me out in some manner. What was noteworthy about the invited jobs is the 29% pass rate. This tells me that many invite jobs end up being low quality, as I didn’t filter them through my typical review process.

BID > WIN > EXECUTE > ?

Let’s take a step back for a minute and contemplate what most freelancers expect from services like Upwork. Everything starts with the supplier posting a new job description. You like the sound of it, so you bid on it with a custom pitch, and in the best case the job is awarded to you. Then you work with the client to execute the outlined tasks, submit for approval, and get paid. The end. Rinse, repeat.

But what if that’s not the end? And what if the beginning – the job description – is actually the beginning to a different outcome? Viewing Upwork through these filters can change everything.

UPWORK FOR LEAD GEN

I’m saying this with minimal hubris, I’m overqualified for the majority of Upwork marketing jobs. That fact hasn’t been lost on gig owners, as I started to get comments back on applications like this:

This was a signal from the market, and I jumped on it. Out of those 16 wins, I got 5 follow-on projects and 1 referral. Those follow-on projects (more work from the same client) had an average per-project revenue worth 2.5x more than gigs I was invited to. The referral project now counts as my second highest paying one in this span of time.

But, wait, there’s more. Nearly 45% of the business I won involved greater scopes than the original job posting covered. I don’t have exact numbers on the increase in revenue associated with these larger scopes, as many original job descriptions only have budget ranges or, worse yet, no real associated fees yet. Regardless, this means that almost half of the jobs won were closed for more cost than the poster intended.

From my many conversations and consultation with Upwork job owners, particularly in the marketing strategy category, I can confidently say that most of these folks need guidance. That makes obvious sense if you see marketing strategy = marketing advice = marketing guidance. Extrapolate that out a bit further and you can start to get a feeling for their mindsets going into posting an Upwork job for seeking a marketing strategist. That is, they need someone to come in and tell them what they should be doing.

That’s why I began to assume the job descriptions are only starting points. A job owner posts a gig for someone to author a few blog posts, maybe what they really need is a well planned content strategy. Actually, this exact thing happened to me. I turned a job for 3 blog posts into a full research and strategy project, because that’s what the client actually needed.

Getting the most out of Upwork requires a little different view of the platform. Some people will come to the site, follow the typical flow of a job seeker, and simply do the expected. But others will seek the opportunity to source new client leads in new ways that turn the transaction a bit on its head.