Win More Freelance Jobs with These 5 Cold Email Strategies [Bonus Templates Included]
Everybody knows that being a freelancer and winning freelance jobs comes with its own set of pros and cons.
Pro: Your income isn’t capped at some arbitrary number (based loosely on your level of experience and the mood of the person hiring you).
Con: Every dollar you earn relies on your ability to not only deliver the work, but go out and secure well-paying projects.
… Over… and over… and over again.
(Unsurprisingly, a study by Elance and Freelancer’s Union discovered that “finding new work” and “maintaining stable income” are the two biggest challenges cited by freelancers).
If you’ve ever found yourself on the wrong side of a feast or famine cycle, you know exactly what I’m talking about. Finding freelance jobs and new clients outside of your referral network usually takes more time, energy, and resources than actually doing the work.
It would be great if clients were beating down your door, or you had a never-ending stream of referrals coming in (we can all dream).
But in reality:
At some point we all have to turn to the “cold pitch” to fill up our client pipeline in hopes of winning more freelance jobs.
And if you wing it, it’s not going to be fun. Expect desperation, insecurity, and spiralling morale (trust me, I’ve been there).
This is why I hear a lot of freelancers say cold pitching “just doesn’t work”. Well… those freelancers are dead wrong (and my business is a living proof).
Sure, some failure and rejection is to be expected when you’re coming in cold…
But if you are strategic about the way you pursue cold prospects, you’ll find yourself spending a lot less time chasing new freelance jobs and more time doing the work you love.
(Side Note: This guide is a sampling of what we cover in Digital Freelancer’s Freelance Academy. If you’re interested in leveling up the business side of your freelancing, go and check it out!)
Let’s get started:
Here are five cold emailing strategies I’ve used to land freelance jobs more frequently.
Strategy #1: “Don’t Swing at Nothin’ Ugly”
That’s the advice sales expert Jeb Blount heard from the coach during one of his son’s little league baseball games.
Down by one, with two runners on base, and two outs already secured… the next batter was firmly instructed:
“Don’t swing at nothin’ ugly.”
Basically, the coach was telling the batter not to swing at any pitches way outside of the strike zone.
But Jeb quickly realized the implications for salespeople as well…
By the way, if you don’t consider yourself a salesperson — SPOILER ALERT! — you are.
Here’s my point:
It’s really easy to fall into the trap of chasing down every single opportunity that comes along, go through the motions, and end up converting some single-digit percentage of your leads into clients.
Many freelancers in this situation would think to themselves: “Alright… low conversion rate, no problem. I just need more leads.”
But consider this:
You’re only converting a fraction of your leads because you’re chasing bad freelance jobs and opportunities (and wasting a ton of valuable time in the process).
Just like swinging at wild pitches will drop your batting average… chasing “bad fit” clients will seriously lower your client win rate — and lose you time, money, and peace of mind in the process.
Now that we know what we shouldn’t do, let’s dive right into the next section.
Identifying Ugly Freelance Jobs
At this point, you might be saying: “Ok Connor, I know I shouldn’t chase down every opportunity, but how do I know which opportunities are the ‘ugly’ ones?”
That’s an important question to answer. But luckily for us, it’s not impossible.
Here are a few examples:
- The person you’re connected with isn’t the primary decision-maker;
- The company you’d like to work with doesn’t have the budget for you;
- The work is so complex (or the pay is so low) that the project will barely be profitable;
- The client has unrealistic expectations of the project, which has negative implications for the timeline, budget, scope, and client management requirements.
If an opportunity meets one or more of these criteria, odds are it’s never going to translate to new work in the first place, so why bother?
That’s why it’s critically important to understand:
- What your ideal client looks like (based on past experiences) and;
- Continuously compare new freelance jobs to that model.
Before you ever commit to a call or meeting with a lead, make sure they’re someone you can actually work with in a productive capacity.
It may seem counter-intuitive at first, but eliminating the lowest quality leads — which probably never would have translated to new work anyways — allows you to focus on the most valuable freelance jobs.
Here’s how to put it into practice:
From the very first email interaction, constantly evaluate the current opportunity against your ideal one.
Ask questions like these:
- What is your timeline for making this decision?
- Is there anyone else we should loop into these conversations?
- Have you earmarked a budget for this project or is that an area I could help you better understand?
- Have you worked with freelancers in the past? What was that experience like?
- How would you define success when it comes to this project?
Each of these open-ended questions gives the client an opportunity to share information that helps you determine whether or not this particular project is in your wheelhouse.
If it’s not, don’t be afraid to politely opt out and look for something better.
Unless you’re desperate for the income, you’ll save time and avoid a few headaches by referring these freelance jobs to someone in your network.
Strategy #2: Communicate Your Understanding of Their Problem (and a Solution) as Quickly as Possible
Think about the emails you exchange with your friends, family, and professional contacts (the ones you actually like) for a minute.
Odds are, the language and formatting are a little different from the last email you sent to a client.
You’re probably not addressing them by “Mr.” or “Mrs.”, and you’re most definitely not rambling on about how great you are or sharing things they don’t care about. That’s the way you should interact with prospective clients.
Always keep your cold email pitches personable, clear, and concise.
You want to come off as a real person who is reasonable to work with, knows their stuff, and respects the prospect’s time.
How do you put this into practice? It starts with the subject line.
Which email are you more likely to open?
- Freelance Web Developer
- Your Web Design Project
- John, an issue with your website is turning away customers. Want some help?
The first two emails could have been sent by any freelance web developer to any company with a website, i.e. bulk spam alert.
On top of that:
There’s nothing that communicates either of these freelancers have done their homework on the client.
The third email, on the other hand, quickly and clearly communicates that you know the following:
- The client’s name is John;
- John needs help fixing his website;
- The “brokenness” of his website has a monetary cost;
- You care about the success of his business;
- You’re capable (or you know someone who is capable) of doing the job.
In just a few extra words, John has 10 times more confidence that you can help him out, compared to those other two freelancers.
This brings us to one of the most valuable facts of life you can learn:
People care about themselves more than they care about you.
It seems obvious, but as they say, hindsight is 20/20.
Let’s do a quick exercise:
Go back and look at your last five email pitches. I bet more than half of them start with the word “I” (if I’m wrong all the better — but it never hurts to review the basics):
I’m interested in learning more about your web design needs. I’m a freelance web developer who is comfortable designing custom WordPress themes and I’m also well-versed in front-end design.
Okay… now think back to all of those emails you get from friends and family. How many of them go something like this?
I’m interested in learning more about your plans for tonight. Remember, I’m a friend of yours and I’m pretty good at skee-ball, mini golf, and bumper cars. Also, I’m also pretty good at telling knock knock jokes.
That person would be the most annoying friend in the world, right?
But freelancers send that kind of email every single day, because it’s easy to write and it feels like you’re selling your services by addressing client needs.
Your heart is in the right place, but the execution needs some refinement.
Let’s flip that cold email approach on its head:
Getting your website to look good on all devices can be a real pain. Just when you have it looking perfect on desktop, you pull out your phone and suddenly…CHAOS!
Most of the big names in your industry have gone to custom WordPress themes to address this issue. Many theme templates come responsive out of the box, and with a little love from a developer you can customize them to quickly get a clean, professional website that looks great on every platform.
If you’re open to it, I’d like to share some ideas for how you can solve your responsive web design challenges.
Now, call me crazy… but that just feels different when I read it out loud. It feels like this person is focused on my needs, not theirs.
They aren’t trying to sell me a project. They’re trying to help me solve a problem and want to share some proof that they’re capable of delivering that for me.
Now, what do you do if you don’t have many (or any) project details?
This is a common scenario when cold emailing, and it’s totally okay.
Just ask for more details:
It looks like you’re having some frustrations with your website being broken on smaller devices like tablets and phones. Are you familiar with responsive web design?
Basically, it’s a new standard for designing websites the look great on all platforms, including desktops, laptops, tablets, and phones.
Making your website responsive can be difficult (and frustrating!) if you don’t know what you’re doing. Have you considered hiring a web developer to help you out with this?
If so, I’d love to share some information that will help you find the right developer for the job. Would it be okay to follow up with a few pieces of guidance?
This version of the pitch email will give you three important pieces of information:
- How tech-savvy are they? Do they know what responsive web design is and what that means for their business?
- Is the lack of a responsive website a painful or annoying problem for them? Are they open to hiring a web developer to make this pain go away?
- Do they find you somewhat credible? Are they willing to take your advice to help them solve this problem?
This email also communicates that you:
- Understand their problem;
- Know what the ideal solution is;
- Are willing to help them solve the problem, even if they don’t choose to work with you.
This is the type of interaction that helps you qualify potential freelance jobs (see Strategy #1) and form strong relationships. Both of which translate into ongoing work or professional referrals.
The short version of this strategy is this:
The minute you feel you have a solid understanding of the client’s issues, start communicating that as clearly and concisely as you can.
Strategy #3: Communicate YOUR Value Only in Terms of Benefits and Outcomes for the CLIENT
Now, you might be saying… “But Connor, this is a cold email. These people have no idea who I am. Shouldn’t I be telling them about my skills and qualifications?”
…and you’re right.
At some point you have to prove that you can deliver on the recommendations you’re making to the prospective client.
My point so far has been that you don’t want to lead with that, as many freelancers tend to do.
Here’s what usually happens:
After you’ve kicked things off and made some sort of personal or professional connection, the conversation will eventually lead to:
“What makes you qualified to work on my project?”
At this point, you have to be extremely diligent: It’s easy to fall into the trap of using too many I’s and Me’s, and not enough You’s and We’s.
Let’s say a prospect came back to you with something like this:
Thanks for the note. Yeah, my website definitely needs some help.
I would be open to hiring a developer. Do you have any experience in this area?
That’s a clear opening to come in and start selling yourself. You’re one step closer to closing this new opportunity!
If you start talking in a language that the client doesn’t understand (or care about) you run the risk of losing them.
Here’s what a typical response might look like:
I can customize WordPress themes pretty quickly. Here are some WordPress sites I’ve designed in the past: Link 1, Link 2, Link 3.
If you’re looking to bring someone on, I could start working on this project in the next week or so. What do you think?
What’s wrong with this picture?
Sure, it gives John a sense of how experienced you are, but he probably has no clue what any of those programming languages are.
Depending on his level of technical knowledge, he might not even understand what you mean by “back-end” or ”full stack” or even “WordPress.” He also probably doesn’t care much about your professional career path.
Here’s what you do instead (and also the key to cold email strategy):
Communicate your personal value in terms of the client’s needs, goals, and desired outcomes.
The easiest way to do this is to use a common selling framework known as a FAB statement — Feature, Advantage, Benefit.
- Feature: The individual service or aspect of the service you provide.
- Advantage: How that service or service component stands out compared to alternative solutions or competitor offerings.
- Benefit: The tangible, positive outcome the client can expect to see because of this feature. Answers the question, “So what that means to you is…”
So, let’s try that email response again.
But this time we’re going to use client-focused language and a FAB statement:
I’ve been designing responsive websites for the last three years using a platform called WordPress as the foundation.
Roughly 25% of all websites are built on WordPress, because it has a large developer community that creates responsive website templates that you can then customize to meet your needs.
Starting with a responsive template cuts down on development time and removes the need to continuously test your website on multiple devices (the template creators have already done that). At the end of the day, that means you get a website that is tailored to match your professional brand, looks beautiful across all platforms, and can be easily updated by someone on your team.
Here are three examples of WordPress websites I’ve designed for other clients: Link 1, Link 2, Link 3.
Can we set up a 30-minute call later this week so I can talk you through the process?
Can you see the difference?
Number 2 is laser-focused on the client’s specific need — a responsive website design — and the ideal solution — a customized WordPress site.
Version 1 used some form of the word “I” 8 times, while Version 2 only uses it twice.
The 2nd iteration also leverages the FAB structure to present your qualifications in a client-focused format.
Let’s breakdown how we did that:
Feature — Three years of experience developing responsive websites using WordPress.
Advantage — WordPress is a tried and true website design platform that allows you to customize an existing responsive website template.
Benefit — So, what that means to you is… you get a website that looks beautiful on every device, can be easily modified by your team, and can be developed much more quickly and affordably than starting from scratch.
In my opinion, Version 2 does a much better job of communicating your credibility and selling your services to John.
The key here is to gauge the level of industry knowledge your prospect has and use the language that will communicate the value of your services in their terms.
And remember, always avoid:
- Technical jargon
- Me-focused language
- And the dreaded “feature dump”
Do this, and you, your sales process, and your freelance business will be better for it.
Strategy #4: Set Clear Expectations and Share the “A Day in the Life Of…” Story
As a cold email evolves into a back-and-forth discussion, many freelancers tend to present the working relationship like this:
- You need a responsive website design;
- You sign a contract to pay me money to design your website;
- A couple weeks later, you have a shiny new responsive website.
That’s certainly a nice and easy summary you can quickly communicate via email, but we all know that’s not a realistic reflection of how things will go.
What about the website specifications? Collecting of brand assets? Sourcing website content? Handling revisions? Swapping out the old website with the new design? Handling downtime, bugs, out-of-office obligations, lagging response times, client stakeholder push-back….
You need to remember:
… this kind of stuff can really upset a client if they aren’t prepared for it.
So, after you use the first three strategies to go from cold lead to warm lead, here’s what you should do next:
Share what I call the “A Day in the Life of a _____ Client” story.
Here’s the truth:
They only care about a handful of things:
- What is this going to cost me?
- How quickly can we get this done?
- What do you need from me?
- What kind of hiccups could delay or stop progress?
- How will my business be better off for making this decision?
That’s pretty much their core focus when it comes to working with you.
If you want to deliver an outstanding client service, start addressing these concerns early on with direct, transparent language. The more you avoid surprises, the better.
Here are two ways to address the above items:
- A scoping document or client on-boarding package (long-form)
- Little references in emails early in the selling process (ad hoc)
For example, you might drop in an “A Day in the Life of” snippet at the end of an email by saying:
… If we wanted to start this project next month, we would have to get a 60-minute call on the calendar by the end of next week. During that call, we’ll discuss what you like and don’t like about your current design, capture any specific needs you have for your new site, and collect all of the graphics and content pieces that need to be transferred over.
If we can lock that in, I think we could start this project on the 1st and I could reasonably have a first draft ready for you by the 10th.
Sharing something like this, especially when you haven’t technically sold the work yet, can go a long way toward closing the deal.
One: It shows that you are intentional about your work.
Two: It illustrates that you have a process for delivering on time.
And three: It lays out exactly what you need from the client to make that happen.
These kinds of insights can be peppered in throughout the selling process to give the client a feel for what it’s like to work with you and set expectations for the potential working relationship.
When done correctly, they establish you as a qualified professional and build that critical layer of trust that separates great client engagements from “so-so” freelance jobs.
Strategy #5: Close Out Every Email With a Clear, Active Call to Action
There is nothing that makes me cringe harder than reading a cold email that ends with, “Let me know if…”
Of all the cold emailing mistakes that freelancers make, this is probably the most common and most devastating.
How can such an innocent phrase be such a huge opportunity killer?
A few reasons:
- It puts the responsibility on the client to tell you what the next step is;
- Leaves the interpretation of what that next step should be up to the client;
- And gives the impression that you don’t have a process or you don’t know what you want.
Think about what ending an email with, “Let me know how you’d like to move forward” sounds and feels like to a potential client…
“Move forward with what? You haven’t done anything but tell me who you are and what you do.”
“There are a million ways we could move forward. I could just write you a check, send you some website designs I like, fill out a scoping document, or I could put you in touch with my marketing lead. Which one is the right one?”
“When and how should I let you know? Do I respond to your email? Do I call you? Should I get back to you today? This week? Next month?”
Why do so many freelancers default to this?
Generally, because they don’t want to sound pushy.
But from the client’s perspective, it ends up sounding like you don’t have a plan.
Your purpose as a freelancer is to take work away from your clients and solve their problems, not give them more things to worry about.
So how do you avoid the “Let me know…” trap?
End every email with a clear, active call to action.
To do this, you can choose one of two approaches:
- Ask a clear “yes or no” question. Example: I think that there are some opportunities to improve your website in a way that will generate more sales. Would it be okay if I send you a few ideas around how to improve your conversion rate?
- Provide directive instructions on what to do next. Example: It sounds like the best next step would be to set up a quick 30-minute call so that I can better understand your specific needs. Here is an up-to-date link to my calendar: [LINK]. Let’s book a call sometime in the next week.
The goal here is to minimize the demands placed on the client for moving the conversation forward.
This is the single best way to increase responses and land more freelance jobs.
This strategy is a simple tweak that leaves many freelancers feeling skeptical, but they almost always come back to me a few weeks later saying things like, “This stuff really works!”
Next time you’re drafting a cold email, swap out your usual closing statement with an active call to action… I’d love to hear about the results.
BONUS: Get My Best Email Scripts for Three Common Freelance Selling Scenarios
Starting a cold email campaign can be scary.
But if you use the strategies I’ve laid out in this article (and the templates you’ll get by signing up for the three bonus templates), you’ll find that reaching out to potential clients is a lot easier (and you’ll win more freelance jobs) when you use a strategic approach.
Want to help contribute to future articles? Have data-backed and tactical advice to share? I’d love to hear from you!
We have over 60,000 monthly readers that would love to see it! Connect with me on LinkedIn and let's discuss.