How to Pitch Freelance Services to Small Businesses

Joshua Kraus

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Most freelancers share a common dream. No, not the one where the IRS nixes all of your coffee shop tax deductions. It’s the dream of never having to pitch to clients. No more cold calls or unsolicited emails. No more selling your services to strangers. It’s a dream of self-replicating referrals.

But the road to that dream is paved with pitches. And you know what? Pitching doesn’t have to be a drag. With a good strategy and the right attitude, it can lead to great clients and rewarding work.

Small businesses are great places to start pitching.

For one thing, it’s much easier to get in touch with the owner of a small business than the owner of a large corporation. Small businesses also have limited manpower and a whole lot that needs doing, which means your services are likely needed, whether the client knows it or not.

However, pitching to a small business requires a different mindset than pitching to a larger company. To make a successful first impression, win a small business client and earn fair compensation, consider the following advice.

Understand A Small Business’s Priorities

Andrew Martin is a freelance web developer who has worked with businesses of all sizes. His experience has taught him that smaller businesses prioritize things much differently than larger ones.

“Smaller companies seem to be more focused on things like design,” Martin says. “While larger companies tend to be more focused on the overall communication strategy.”

Martin explains that larger businesses often have marketing teams in place to handle big picture issues such as brand identity and messaging. Therefore, the more immediate concerns skew toward the technical, and include things like content and usability.

But most of the mom and pop shops Martin has worked with don’t have anyone in charge of marketing. With nobody around to handle larger branding issues, small businesses often direct their attention to more tangible concerns, like the look and feel of their website.

To get a foot in a small business’s door, start the conversation by aligning yourself with their priorities. Focus on how you can help them improve things they understand, such as design and page rank.

You can introduce overarching goals like brand identity, social media strategy and customer conversions once you’ve got their attention. Not every small business owner understands these issues, and although the big picture stuff is still important, it’s not always the best ice breaker.

Bring Up Competitors

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Fruit-shaped bean bag chairs, upside-down umbrellas, real fake doors; no matter what the niche, a small business is likely going to have competitors. It might seem counter-intuitive, but weaving the competition into your pitch can actually enhance it.

This is how Martin does it: “I find another industry competitor that has a nicer site than them and say ‘Hey, this guy is doing this,’ or ‘This guy has a really nice way of presenting information.’”

Then he explains to the client how he can elevate their business to the level of its competitors.

This strategy works because it allows Martin to explain what he can do for the client in terms the client can understand. Showing a client your previous success stories can also be effective, but unless those success stories are inherently similar to the current client’s circumstances, it may be difficult for the client to connect with them.

Don’t Look Like A Scam

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Every small business owner has no doubt received spams and scams by the gigabyte.

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The more spams and scams a small business receives, the more jaded they will become toward anyone legitimately offering them their services. Therefore, it’s vital that freelancers avoid looking, sounding and acting like a scammer.

Aside from not using all caps, the best way to reach a small business is by personalizing your communications. Do your research. Get to know the business. Tailor your messaging to the specific company, and if possible, the specific person you’re contacting. Here are a couple tips:

  • Address the recipient by name.
  • Start the email by quickly explaining how you heard about them (“I was looking for a new restaurant to try and came across your website.”)
  • Explain why you’re contacting them (“I’d like to help you increase conversions.”)
  • Show them you possess a nuanced understanding of their problem (“Restaurants face some of the fiercest SEO competition around.”)
  • End with a call to action (“I’d like to go over the details sometime this week.”)

Be Prepared For Hand Holding

Davina Van Buren is a freelance writer who has noticed that smaller businesses require much more hand-holding than larger ones.

“I have to guide a small business owner along a lot more than when I’m working with a larger company,” Van Buren says. “It requires a little more of a personal relationship with the client, and therefore that personal relationship is equally as important as your writing, or whatever you’re doing.”

Freelancing for a small business is a much more intimate experience than completing assignments for a big company. With the latter, you role is typically more cog-in-the-machine, but small businesses want you to take the lead.

To sell a small business on your services, you need to come across as a subject matter expert. You’re offering them something they cannot do themselves, so when pitching, don’t ask what you can do for them, tell them what you can do for them. Don’t look for permission to do something, explain why it’s a good idea.

“It’s really important for them to feel like they can trust you with their baby because often, that’s what it is,” Van Buren says.

Explain Your Value

Both Martin and Van Buren have consistently found that small businesses don’t always understand the value in their specialized services.

“I’ve found that a good amount of people think web development is super cheap and easy,” Martin says. “They can’t see the difference between a good developer and a bad one.”

Many small business owners think that anyone can make a website, that anyone can write copy. To sell them on your services, you have to make them see your unique value.

Whenever Van Buren brings up her figure and sees the shock on a client’s face, this is what she does:

“I try to explain to them that it’s not just throwing out some words on a page – that it is conversions, that a good writer knows how to use psychological tactics to sell things, to persuade the reader.”

Van Buren also makes sure the client understands how her services pay off in the end, and describes the work she can do for them as an investment.

Take Initiative

Small businesses often know they need help with something, but they may be unsure of what that something is. As a freelancer, it’s your job to highlight what exactly can be improved, and establish how you and you alone can do the improving.

Taking the initiative goes beyond the initial pitch. If you succeed in landing a client, you should continue to point out areas of improvement, and offer to help.

“Part of what a good freelance writer does is to offer what other things they can do,” Van Buren says. Take the initiative instead of waiting around, hoping you’ll get more work.”

For example, a client might not know what a case study is, but it could be very beneficial to their business. They might not realize a freelance writer can help with things like blogging, copywriting emails or creating press kits. They might not be aware that a freelance developer can also help with continuous website maintenance, SEO visibility or social media integration.

“Small businesses are busy with the day to day operations,” Van Buren says. “They don’t have time to think about marketing or start blogging.”

It’s your responsibility to convince them that tasks like these are necessary, and you’re the best person to handle them.


Small businesses and big companies are two different animals. While multi-department organizations possess a clearer understanding of their long-term needs, smaller businesses are more concerned with the day to day, and are thus more focused on the short-term.

To approach them when offering your freelance services, it’s important to first appeal to their priorities. Explain what you can do for them in terms they can understand. Prove you’re not just one of a hundred identical spam emails by personalizing your communications and establishing a rapport. Find something in your life that connects you to their business and make it a point of virtue.

Pitching small businesses can be hard work, and demands a lot of research and a fair share of trial and error. But just like your services, pitching will pay off in the end.