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Sales 101 for Freelance Devs — Avoiding the Pain You’re About to Experience

Back in March, I made a fake tweet for a blog post draft.

It was a blog post about how not to handle a situation where your large, only client (i.e. your salaried employer) abruptly breaks up with you.  But given that the economy collapsed in on itself like a neutron star a week later, the post seemed in poor taste and I never published it.

Still, no sense letting a good fake tweet go to waste.  So I’m going to use it instead for a post about freelance dev sales, which is basically a rounding error away from salaried dev job interviews.

What I’m going to do is walk you through the sales strategies that a dev freelancer will suffer through, in numbered order, before figuring out something that actually works.  I’ll also have a couple of interludes to explain a little bit about sales along the way.  The goal is that hopefully you can skip some of missteps and create a strategy for faster joy.

1. Introduction to Affiliate Sales: The I Just Got Fired Tweet

Here’s something that seemingly every developer tweets at some point in their career:


Usually it has approximately 8 billion retweets and likes, a handful of comments, and, I’d assume, a conversion rate just north of the Planck constant into useful job leads.

Why would I presume that?

Well, because the call to action invites people to do something super easy.  “Smash that retweet button and do your good deed for the day.”  So people do… exactly, and only, that.

And then they call it a day, assuming that someone else down the line will do the actual thing that might help this person.  And, if it ever happened, the “actual thing” would probably be just introducing them to a corporate recruiter or, maybe a dev manager or something.

It’s a classic case of vanity metrics in the world of marketing.  But I want to talk about the sales strategy here.  Let’s save freelancer marketing for another day.

Interlude: Understanding Affiliate Sales

From a pure sales perspective, this “please someone help me” tweet is the absolute laziest and least effective imaginable strategy.  Understand that I say that with no judgement about the newly unemployed person.  After all, they’re:

  1. In a really tough and vulnerable place and
  2. Not seeking to be a business owner or a sales person

But let’s really look at this as a strategy for selling person-hours of labor (which is what all salaried software engineers and hourly freelance developers are actually doing).

This is a sales strategy wherein the hours vendor neither executes his own sales, nor does he hire someone to handle his sales.  Instead, he relies on affiliates to handle lead generation for him.

To understand affiliate sales and marketing, watch this.  Here’s a link to a book about sales by some dude named Ken Wax.

I have no idea who Ken is, and I assume that he has no idea who I am.  But, that doesn’t stop him from employing me in his sales organization.  In my link, I used a special little thing called an Amazon affiliate code, which you can see in the screenshot here:

With that affiliate code, if I successfully get you to buy Ken’s book, I make a little tiny bit of money from your purchase.  (It’s actually Amazon paying me, but the model remains — sell other people’s stuff for them, and they give you a cut.)

In this example, Ken (Amazon) is crowdsourcing his sales.  “I’m not going to do anything at all to sell my book, but if you do all of the sales work for me, I’ll share with you a chunk of the proceeds.”  It’s a model that works well-ish for lower ticket items and, well, when you actually pay the affiliates.

2. “Networking” as an Affiliate Seller Strategy

Let’s go back now to the “I got fired tweet,” and how it’s an example of lazy, cheap affiliate sales.  Here’s what that tweet really says.

I’m not going to sell my own person-hours, nor hire someone to do it for me.  Instead, I’m going to rely on you, my Twitter followers, to be my sales force.  And for your trouble, I offer you nothing except a tiny drip of dopamine for the feeling of helping me.

This is why I call it both incredibly lazy and ineffective.

And yet, this essentially becomes the default sales strategy for the newbie app dev freelancer.  “Use your network” means “crowd-source your sales to an uncompensated workforce.”

The difference is that the newbie freelancer doesn’t fire and forget this tweet as half-venting, half-prospecting.  Instead, she employs it as a holistic strategy, announcing to friends, family, and anyone else who might listen that she’s now “on her own and let her know if you know anyone that needs app dev.”

Her friends and family thus become an uncompensated affiliate network for lead generation, usually offering not meaningful references, but “character” ones.

This “strategy” is understandable for a traumatized person tweeting from the phone in their left hand while gripping a pink slip in the right.  The salaried employee only has to figure out person-hour sales once every 5 years or whatever.

But the strategy of uncompensated affiliate sales is ridiculous if you’re an aspiring business owner.

3. Headhunters as an Affiliate Seller Strategy

It doesn’t take long for the “friends and family” well to run dry on you.  Most of them don’t know how to recommend you to begin with, and their patience for doing you favors starts to peter out after the initial desire to support you hanging out your shingle.

Time for a new strategy.

What most freelance app dev folks will do here is turn to the devil they know.  No, I don’t mean former employers, though they probably pitch them too (rightfully so).  I mean recruiters.

Recruiters are, with one an important catch, a slightly different form of your uncompensated affiliate workforce.

Now, I know what you’re thinking.  “Recruiters don’t work for free — they’re compensated.”

They sure are!  Just not by you.

And that preserves the recruiter’s role as affiliate salesman.  But it reverses the roles, makes you the product and the company hiring you the affiliate “seller.”

Weird, right, since they’re not selling?  Well, sure, but it makes sense if you zoom out a little.

An affiliate partner normally makes it cheaper to sell something, but they can also defray cost for something inefficient or labor-intensive. Like hiring you, for instance.

Buying freelance labor is less labor intensive when companies use recruiters, so they pay the recruiters by passing on some of the savings (and probably taking a little bit out of your hourly rate, as well.)

So let’s look at recruiters as a sales force for freelance developers.

It’s actually kinda worse than the “I got fired” tweet.  That tweet casts friends in the role of uncompensated sales staff.  With recruiters, you’re still not compensating your staff, but this time your staff is actively working for the company you’re about to start negotiating with (against).

Yikes!

4. Toptal/Task Rabbit/Upwork as the Same Affiliate Seller Strategy

Let’s move on to a strategy that you’ll probably run either in parallel or once you tire of recruiters.  You turn to a labor broker site like Fiverr or Toptal or whatever.

I’m not going to spend time on this, since it’s almost the same thing, modulo casting a robot as the recruiter.

The resume bot 9000 is the only one that cares about your resume skills section.

Sure, some of these types of sites might take a cut out of your take-home, but don’t get it twisted.  You’re not contributing enough money to flip to customer, rather than product.  Anything they take from you is just kinda salt in the wound.

So we’re right back at square one.  It’s the scenario where your sales staff is actively working for someone else, but this time your staff is an algorithm.

It feels like we’re heading in the wrong direction here, doesn’t it?

Interlude: Sales Is Just Arithmetic

If I were to ask you, “what is sales, anyway” I can imagine the responses I’d get in the comments.  (Go ahead, scroll down and comment if you’d like, but no peeking ahead.)

I’m guessing you’d offer some snark about scamming people or promising things that engineering can’t possibly deliver.  And, depending on the organization, you might be right about one or both of those things.

But that’s not what sales is.  It’s just what some people do in pursuit of it.

Sales, at its core, is a filtration process that you can represent with a Kanban board.  Recall in my “profit 101 primer” post that I talked about sales (“business acquisition”) as one of the three systems of your business.  Specifically:

Acquisition: a funnel-shaped system that takes “the world” as input at the top and poops out customers at the bottom. (e.g. sales and marketing).

Let’s get a little more specific and think of that funnel as having a series of layers, from top to bottom:

  1. Leads — anyone that you think you might be able to help.
  2. Qualified Leads — any lead that you’d actually want to work with and where compensation would align.
  3. Opportunities — the subset of qualified leads that have expressed actual interest in the form of an exploratory email exchange, sales call, etc.
  4. Customers — the subset of opportunities that shake your hand (or whatever passes for that over Zoom these days) and send you a check.

Sales, then, is the system that moves prospects along this path.

An Example of Sales and the Numbers Behind It

Here’s an example of how I might create and represent a CRM in Trello to model this flow.

I’ve done a pretty contrived thing here, so that we can get to the point quickly.  Specifically, I’ve created columns with 8, 4, 2, and 1 cards in them, respectively.

And let’s assume that this kanban board operates where I move things as far to the right as they ever get, and then I leave them there like gravestones marking casualties in the sales funnel.  (Don’t do this in your actual CRM, by the way — there are closed/won, closed/lost columns for that).

Here’s the arithmetic.

Looking back at the data of how my sales process went, I can see that I’ve had 15 total leads.  Of those, 7 became qualified leads, 3 became opportunities, and 1 became a customer.  That’s not super interesting in and of itself, but here’s where it gets interesting.

Crunching Your Conversion Rates and Learning from That

Based entirely on measured, historical data, I know that:

  • Of all of my leads, I only wind up considering 47% of them to be qualified to work with.
  • When it comes to qualified leads, only 43% find me interesting enough to agree to become opportunities.
  • With those opportunities, only 33% of them like my sales pitch enough to become customers.
  • Of all of my leads, only 7% of them will ever become customers.
  • If I want to close a customer, I need to generate 15 leads.

(These hypothetical conversion rates are highly optimistic, by the way — usually you need to generate a lot more leads to get a customer.)

In sales, defining this sequence and quantifying the conversions is everything.  It’s everything because understanding the funnel and the numbers is the only thing that lets you reason about the quality of what you’re doing for each step, and then make informed, rational decisions about how to improve.

Conclusions, Introspection, and Improvement

This is where you might say, “gosh, only 2% of the leads I get from begging on Twitter turn out to be worth my time, so maybe that’s a terrible channel for leads.”  Or, you might say, “okay, letting a robot who works for someone else create opportunities is sure making me whiff on just about every sales call — maybe there’s another source of opportunities.”

Or, maybe it’s simpler than that.  Maybe it’s, “wow, I never realized that you could take a quantified, measurable approach to sales in the first place, so let me try redesigning how I get business, using this newfound knowledge.”

Up to this point in the post, if the freelancer had ever actually defined a CRM, it would probably look like this (note the column names):

You could still, kind of take a measured, quantifiable approach.  But the actual reasoning for decisions in a job interview process is largely unknowable to you, and irrelevant from one customer to the next (e.g. the fact that Bill the Architect didn’t like your shirt in the Lima LLC interview probably has no bearing on, well, anything else on the board).

Finally, in the theme of outsourcing your sales force to robots working for other people, this freelancer “CRM” process is done entirely TO you, rather than BY you.

So if you’re interviewing as part of your “sales” process, stop immediately and build a new sales process.

And that’s a good place to end the interlude.

5. Taking Over Your Own Sales for the First Time: Warm and Cold Outreach

At some point you start to realize that freelancing through recruiters and labor brokerages looks a lot like employment.  This is especially true when it comes to the sales process.  As a freelancer doing “sales,” you’re basically just suffering through job interviews.

This is when the cave dwelling freelancer first starts to move away from the wall and have different thoughts about the shadows.

And that first step generally comes in the form of outreach.  Rightfully so.  You decide to stop abdicating your own sales egnine and to take control yourself.

Now buckle up.  Because, if you’re anything like me, this part is really gonna suck.

It’s time to do some actual outreach, pitching your services to unsuspecting people minding their own business.

Warm Outreach

Most likely, you start with warm outreach.  Warm outreach means that the person you’re reaching out to is somebody that you know.  And this style of outreach differs from affiliate selling in that you’re not asking them to do work for you, but rather trying to either directly sell them your services or else facilitate an introduction to the target of your sales.

You’ll start with warm outreach, but not because it’s the better sales strategy. (And it is.)  You’ll start with it because it’s the least repellent to execute.

And what you’ll probably do is go through your LinkedIn connections and make a list of everyone you know that you think might want general app dev.  These are your leads.  And, if you’re a little ambitious about organizing your outreach, you might even prioritize them, which is a rudimentary form of calling them qualified leads.

Then you reach out and hope to convert them to opportunities.  (Of course, you won’t think of it that way — you’ll just be hoping for a phone call and an agreement.  But it’s what you’re doing.)

The only problem?  The rate at which your warm outreach turns into sales calls might be 10% if you’re lucky.

You’ll get a lot of “ohai, awesome to hear from you, I’ll keep you in mind” and other forms of polite deferral or rejection.  But probably not many actual sales calls.

And, perversely, the ones that you do get will convert from opportunity to customer at a lower rate than they otherwise might.  Why?  Well, because some of them will just get on the phone with you to be polite.

But don’t worry. You won’t have to worry about people getting on the phone with you very often once you blow through your warm leads, and start with the next step: cold outreach.

Cold Outreach

That brings us to the dreaded cold outreach.  You’ll probably only do this once you start worrying about money, and are thinking about going back to Upwork or salaried employment.  And when you reach out, you will likely reek of desperation.

You’re going to send something that looks like this, at 2:02 in the morning, like this dude:

And it goes on and on like this

And, like him, you’ll probably get no response… from everyone.

This is just a terrible piece of outreach (and is a veritable case study in the problem with generalizing).  “I can do anything, so your homework, Erik, is to figure out how to hire me.”  Because if there’s anything people love at 2 AM, it’s a homework assignment to figure out how to give money to a stranger that’s spamming them.

But the point here really isn’t to teach you how to execute good outreach.  It’s to show you how outreach will go for you in the beginning, and what will likely happen.

Outreach as a Numbers Game

Saying that good vs. terrible outreach isn’t the point here wasn’t just a minor digression.  It matters because you’re probably thinking, “well, I won’t do that — I’ll research each person I’m reaching out to and craft a tailored message.”

I don’t doubt that, dear reader.  At least, not at first.

But here’s the thing.

You’re going to lovingly hand-craft those messages, spend a day sending them out to 10 or 20 people, and get absolutely no response.  Then you’re going to do it again tomorrow, and call it a “win” of sorts, that someone literally wrote back to you, “piss off.”  Hey, he responded!

You may earn a “maybe later” here and there, and maybe even a badly qualified sales call.  But your efforts will yield an atrocious conversion rate to opportunities.  And as the days and weeks of this wear on, it slowly dawns on you.

That carpet bomb spammer in the picture had the right approach to cold outreach.  Or, at least, the more economically efficient one.

If only 1 in 1,000 pieces of cold outreach convert, and you only improve those odds to 1 in 500 with lovingly hand-crafted messages, you’re better off just carpet bombing LinkedIn with the spam.

Spammer McGee up there can generate 1,000 of those messages in 2 minutes.  You’re taking months to generate 1,000 and barely having better luck.

Interlude and Conclusion: The Importance of Warm, Inbound Leads

In the beginning of this post, I mentioned that I was hoping to save you some misery.  You can try to attract leads for your business via tweets, recruiters, and robotic recruiters, and it will probably work in some fashion (though, mainly by casting you as a pseudo-employee generalist.)  And you can try to attract leads by pumping your network, and then pumping… well, anyone whose contact information you can find.

But all of that stuff is a massive grind.  It’s a numbers game that you can only win through a combination of sheer volume and slashing your rates.

The key to getting out of all this is to get cards appearing in the leads, qualified leads, and opportunities columns without you doing anything.  The key is to get them to come to you.  And I don’t mean with the help of a robotic job butler working for your “client.”  I mean actual prospects coming directly to you, specifically.

How do you do that?

Marketing is the Key to Sales

Well, I’ve already covered half of the equation in my last post where I told you not to be a generalist.  And the other half of the equation is a topic coming soon to a blog near me: marketing 101 for freelance devs.

As I’ve said and demonstrated throughout this post, sales is a numbers game.

How can you generate the most leads, convert them at each sequential step most efficiently, and spend the least time and money in the process?  That’s what sales is — what it really is — rather than BS-ing people about what you can deliver or trying to scam them or whatever.

And the answer to that question is a surprisingly and refreshingly human one.  You make sales most effective by only engaging prospects that are interested in your services and that would be a good fit for you.  You cut out the noise by cutting out mismatches and doing your best to only engage when the engagement will be a home run.

Which means that the key to a good, honest sales process, is a good, honest marketing apparatus.

So forget outsourcing your sales to unpaid or conflicted affiliates and don’t go overboard on warm or cold outreach.  Instead, start asking yourself the fundamental question, “how can I help good prospects find me on their own?”

Do this, and you’ll effortlessly ace your sales process.

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Helton Moraes
Helton Moraes
29 days ago

“how can I help good prospects find me on their own?”

Wow that sentence is worth the whole post! Thanks!

Last edited 29 days ago by Helton Moraes