How Freelancers Can Win with Cold Email Outreach - Step-by-Step Process and Email Template

Freelancers have a love-hate relationship with outreach emails, which we sometimes call “letters of introduction” or LOI emails. The premise is the same: You email a stranger and attempt to start a conversation.

This marketing strategy can be uncomfortable at first. Cold email outreach is a numbers game. As such, it requires tracking, careful observation, and discipline. Doing it well is time consuming, and though a bunch of apps promise to help you automate the process, there’s really no substitute for highly personalized emails. Boilerplated spam sandwiches are likely to end up in spam folders or cause eyerolls, irritation, or outright hostility.

So why bother? Because reaching out to potential clients by the most direct means available (email) can be a serious game-changer for your freelance business.

Archimedes first postulated that the shortest path between two points is a straight line. When it comes to your bank account (Point A) and a client’s budget (Point M), a humble, ordinary email from your inbox to theirs is the line. My friend Ed Gandia has been banging the landing clients with email drum for over a decade. Gina Horkey at Fully Booked VA has recommended a 10-10-10 Prospecting Process for years. Alex Berman is a huge advocate of cold email outreach too.

So yeah, it’s a thing, and as crazy as the freelance space has gotten with a record-high number of freelancers and the threat of AI, especially to certain types of writers and designers, the persistent bird will get the worms. This post covers an email outreach process that can improve your response rates and land you dream clients.

• Set a goal
• Identify your target audience
• Customize your offer for that audience
• Set an initial price
• Execute your outbound strategy (6 steps)
• Be consistent
• Follow up until you get a clear no
• Adjust your content strategy

Set a goal

Ideally, you can complete this statement:

“I need to identify X number of prospects to send X number of first emails, start X number of conversations, send X proposals sent, and close X number of projects by X date.”

Like I said, cold email outreach is a numbers game.

100 prospects may lead to 80 first emails, 30 conversations started, 15 proposals, and 3 projects.

That’s a rather abysmal 20% close rate, but you get what I’m saying. You must be committed to the process as a whole, and you must turn this big, squishy thing called email outreach into a Morning Marketing Habit: “I'm going to email one decision-maker at one cleantech / solar company each weekday.” You can reverse-engineer the rest of the process based on realistic math and that daily commitment.

Assuming that you’ve identified and validated your target audience (at least to some degree), you’ll be in a better position to guess 1) how many new projects you can take on, 2) approximate number of companies or prospects in the target audience you need to identify, and 3) approximate number of emails you need to send.

Identify your target audience

You’ll have a more strategic approach to your marketing, email outreach included, if you’ve already clarified whom you want to serve and you’ve bent your positioning to fit that audience:

• What industry your dream clients are in
• What your differentiators are, and which ones matter most to them
• Your current track record with clients in that industry
• The work for these clients is one you enjoy
• Clients in the industry are willing to pay what you want to make

Once you’ve picked an industry, it’s usually not too hard to find the names of people who work there and dig up the right email address—e.g., for the marketing director.  If you haven’t already, I would recommend making use of LinkedIn’s Sales Navigator tool. (Check their 30-day trial.) Use the more advanced search criteria to start assembling a list of prospects. You can also use a tool like Dux-Soup to export the list as a CSV file which you can then upload to a GSheet.

This GSheet will serve as your outreach tracker. Voila! You now have a list of good prospects.

You can then start sending connection requests. I recommend sending 10-15 connection requests a day. Skip the message part when sending connection requests because it usually puts people off. Most of these people will probably ignore your connection requests, but some will accept and will even check out your profile and a start conversation with you. Note: This is more likely to happen if you’ve already optimized your LinkedIn profile for that target audience.

Here’s a 49-Step plan for doing LinkedIn the right way.

Customize your offer for that audience

Whether a prospect comes to you (inbound) or you go to them (outbound), you need a juicy offer ready.

For example, let’s say you're a strategist and writer for high-end construction companies and design firms. Your core offer for them is “brilliantly executed case studies that get new project leads.”

The offer’s value proposition goes something like this: Many of these companies and firms have incredible portfolios but weak storytelling. You can pitch them on how you can help them turn their best projects into their best marketing assets. You’ll conduct client interviews on their behalf, and from those interviews, you’ll pull out testimonials, get permission to publish them, and turn those interviews into long-form case studies, short-form success stories, and testimonials.

How do you present the offer to a prospect?

I typically use a GDoc at the beginning. Later, I’ll turn the GDoc into an offer deck with much higher design value, but there’s no reason to waste time or money on eye-catching shapes, colors, and composition until I validate the offer by selling it to 4-5 people.

Here’s my GDoc for my Custom Business Roadmapping Offer. And here’s an example of an offer deck, my 1-Day Brand Sprint.

Validate first. Optimize second.

If you don’t already have a framework for creating Juicy Offers, buy my playbook for $49.

Set an initial price

Regarding price, the cheapest advice I can give is this: Come up with a price you feel good about. What amount of money would you feel good about making for that amount of work?

If you want to be more methodical with your pricing, which I recommend, check out the various posts I’ve written about pricing methodology. Step 1 is here.

And if you’re the sort of person who values your time, buy my Setting Smart, Strategic Prices playbook for $49. It distills the entire methodology into a step-by-step process.

Execute your outbound strategy

Many freelancers don’t know what to do when external threats and pressures like competition, AI, recession, and clients pausing projects cause a scary slowdown in work. My recommendation is to focus on the things you can control—namely, how much time and effort you put into prospecting.

Assume that you’ll always have to hunt for new clients and projects, and build that core competency now—a Morning Marketing Habit. Sometimes, you can get freelance clients fast, but know that one of the most reliable ways to get clients is to email them.

Most people in your target audience still check their own inboxes daily. That means that the most direct path to a conversation is an email.

Instead of waiting for clients to come to you, you go after the high-paying work you want to be doing. Build your dream business one dream client at a time.

Is it easy? Heck no.

But it’s like any other hard thing. You can do it one step at a time. If marketing feels overwhelming to you, simplify your plan. Simplicity is sustainable for you.

Here’s the cold outreach plan I recommend for freelancers:

1. Make a list.
2. Put together a list of 100 prospects in your target audience—e.g., SaaS startups, local food and beverage companies, fashion influencers, independent technology consultants. (There’s a mouthful.) Even if only a fraction of those 100 new prospects become paying clients, you’ll end up with more business than you can handle. You’ll be in a position to rehome the bottom 20% of your current client base.
3. Put name, company name, website, email address, LinkedIn profile, and notes for each person in a GSheet or CRM. Note: Using LinkedIn and Google searches, it’s often easier to find the company name first and then find the decision-maker (e.g., VP of Marketing).
4. Do your due diligence first. One-size-fits-all messages are often ignored or deleted altogether, so send highly personalized emails, not boilerplate spam sandwiches.
5. Take the time to do research on your recipients and learn about their businesses, interests, and any interesting trends.
6. Mention something specific in your email that shows you've done your homework. (I’ll show you specific examples in the outreach email template for freelancers I give away for free at the end.)
7. Track your results. You want to improve your outreach effort over time. If you don't get responses to your early emails, you can iterate and try different content in the next email. To do that, you have to keep some kind of record of the following:
8. In the same GSheet or CRM, keep track of prospects you’ve emailed.
9. Keep track of the subject line you used. Make your subject line catchy and intriguing. Avoid clickbait or overly salesy subject lines. A well-crafted subject line piques curiosity and encourages the recipient to open your email. I typically use questions: “Are you interested?” Your subject line is the first thing your recipient sees, and it can make or break your email's chances of being opened. Your brilliant email is a dud if the client never opens it because the subject line sucked. So at the beginning of an effort to connect with potential clients, the subject line is the single most important piece you need to experiment with and improve.
10. Track read receipts / open confirmation. You want to track whether or not people are opening your emails because if they're opening your emails, then that is a signal that your subject line is working. Check out Boomerang or Yesware and figure out which of those tools is best for your email service provider. (Or maybe your ESP already tracks opens automatically.)
11. Play around with length.
12. Try both short emails and long emails. As with all written content, effectiveness matters more than length. If your short email is boring, people will delete or archive it. If your long email is entertaining, helpful, intriguing, or otherwise valuable, then people will keep reading it.
13. Track response rates. If one particular email gets a high response rate, then you know the content, short or long, is doing its job.
14. Experiment with different calls to action. Your calls to action can produce mixed results, the same as with subject lines and length. I've sent a lot of Letters of Introduction and pitch emails and the ones that end in a question or that have the initial call to action be a question tend to get a higher response rate than the ones that are just sentences. Questions start conversations, and that is the goal of your first email, start a conversation.
15. Include a strong call to action in each email.
16. Copy and paste it into your spreadsheet.
17. Track response rates. If one particular CTA gets a high response rate, then you’re on the right track.
18. Put together a winning combination (eventually). You are a scientist in a laboratory performing experiments.
19. Track the results so that you can start to put together the subject line that gets the highest open rate and the body content and call to action that get the highest response rate.
20. Try new experiments from time to time—e.g., an email with a Loom video message in it. Or, maybe your experience contradicts mine. You discover that ending your emails with a question is less effective. You try different CTAs until your results improve. You get smarter and better over time if you keep paying attention.

Be consistent

Commit to sending one letter of introduction per work day.

By the end of the month, you will have sent 20 letters of introduction (don’t think of it as a pitch).

So even if, out of hundreds, just half respond and only 20% turn into actual conversations, it could still totally transform your business.

Follow up until you get a clear no

I have started conversation and gone on to win projects after 4-5 follow-up emails. I’ll never say “I'll wait to hear from you” because then I’ve put the ball in their court. I always follow up with the prospect.

Always assume that the answer is yes until you get a clear no.

The challenge is obviously finding a creative way to do it. One way to stay top of mind is to go find a valuable resource and send it to them. You can do any of the following:

• Find a really great podcast episode and say, “Hey, I really enjoyed this episode. This guy is a super smart marketer. Thought you might appreciate this.” And then you share them the link to that podcast episode.
• Put together a preliminary plan and just say, “Hey, it's been about a month since I checked in with you. I was thinking about you this morning. I spent 15 minutes organizing my thoughts. What do you think?”
• Check out their socials and find something they did recently: “ “Hey, I stumbled across your Instagram. How is Alaska? I've always wanted to go.”

You don’t even mention the project. You're just popping up on the radar again. So while the other freelancers your client has talked to are just sitting around waiting to hear back, you’re being proactive. The consistent and proactive bird gets more worms. Maybe the early bird does get the word worm sometimes, but the proactive, consistent bird gets a lot more of them.

Don’t be afraid to steal my 12 follow-up email templates.

Adjust your content strategy

Once you have your goal, audience, offer, price, and outbound strategy defined, then you can create content and publish it on LinkedIn (or wherever) to support the offer. Your own content strategy is gonna be much more focused if you know what specifically you want to sell and to whom.

When you do start a conversation, you already know what the offer is and what the next step for them is too. If the person has no budget for your higher-priced offer, you can downsell them to a lower-tier offer.

For example, I know I want to sell 30/60/90 plans, what I call a “Custom Business Roadmap,” to growth-minded freelancers who struggle with focus and second guessing. I wrote this LinkedIn post about the focus problem. It sparked a conversation with a Webflow specialist in my DMs, and within a couple of days he had paid for the engagement in full, up front.

That’s what happens when you write posts about the problems you want to get paid to solve and have your juicy offer ready.

When the price point is too high, I offer a Clarity Session instead.

Also, make sure that you optimize your LinkedIn profile for “your offer.” To do that, I would encourage you to optimize your LinkedIn profile. For example, add something about your offer” to your LinkedIn title. Turn the first “entry” in your Experience section into a miniature landing page for your offer.

Using LinkedIn effectively requires a paradigm shift for many freelancers. Your profile is a landing page, not a resume, and you must drive traffic to it by sending connection requests, leaving comments on other people's posts, publishing your own posts, and then optimizing your profile with hashtags and keywords so that it shows up in more searches.

Sidenote: I would also recommend having some kind of advice or strategy offer for every new client. A major turning point in my business in early 2016 was when I started selling strategy. I shared why and how I started selling strategy as a standalone offer in this conversation with Ed Gandia. The first engagements I sold were content roadmapping and project roadmapping, where I helped people organize their thoughts, pinpoint the right strategies and tactics, create an actionable plan, and, to some degree, decide how to spend their budget.

Think of it as getting paid to create your proposals. David C. Baker and Blair Enns talk about that in this episode of the 2Bobs podcast.

Closing Thoughts on Cold Email Outreach for Freelancers

When we start marketing, we have to keep asking ourselves the right questions:

• What business do I really want?
• Who would be an anchor client?
• What juicy offer can I put in front of them?
• How do I start strategically start doing that?

Make a plan, and keep it as simple and actionable as you can. Simplicity scales.

When I recently had a 1-on-1 session with a freelance strategist and copywriter, I encouraged him to put together a plan of 1’s:

• 1 target audience
• 1 retainer offer
• 1 initial price
• 1 outbound strategy (Email outreach)
• Optional: 1 secondary strategy (LinkedIn)
• 1 call to action
• 1 email per day

If you have one offer for one target audience, one primary strategy, one secondary strategy, one call to action, and simplify, simplify, simplify, sure enough, you're gonna close more sales than most of your competitors.

It’s no surprise that Ben wrote this in an email soon after: “Thanks for all your help. I made more progress in my marketing strategy in the last week than I have all year. Looking forward to our call next week.”

If you want the same cold outreach email template I shared with Ben and a short video tutorial showing how to customize it, put in your name and email address below.

When you’re ready, here are 3 ways I can help you:

1. Freelance Fixes. This short guide walks you through 6 small but important “fixes” that you can make to raise your income without working longer hours. People really seem to like it.
2. Morning Marketing Habit. This course will help you build an “always be marketing” practice, become less dependent on referrals, and proactively build the business you want with the clients you want. My own morning marketing habit has enabled me to consistently make  6 figures as a freelancer.
3. Clarity Session. It’s hard to read the label when you’re inside the bottle. I've done well over 100 of these 1:1 sessions with founders, solopreneurs, and freelancers who wanted guidance, a second opinion, or help creating a plan.