• Larissa Lewis

I write (and get!) hundreds of sales emails per week—here’s what works

As a business owner, I get hundreds of sales emails per week. You can count up its many bonuses, but LinkedIn is a hotbed for sales pros crawling for email addresses to fire off cold pitches. As a writer, I read each and every one I get!


Yes, I said it—I love reading cold sales pitches (even the ones that end up in SPAM)—almost as much as I appreciate helping people write effective ones.


Businesses are pitching to me just as clients use my writing to pitch to theirs. In any marketing project, it's always important to sit in the seat of your customer for a moment—and hundreds of businesses give me that chance every week.


If you're a business owner writing your own content, or someone with an unrelated job that's forced to wear the writer's hat, it feels like an uphill battle when it's time to pen those cold sales emails, doesn't it?


🤯 It can feel nerve-wracking, it can feel like an ambush if you’re not used to the practice—what? I have to write WHAT by WHEN?!


🤯 It can feel even more taxing when it’s open-ended: how do you know when to pull the trigger and send or publish?


🤯 As I mentioned in a previous post, starting projects with no perceived endpoint are perhaps even more jarring—they can nearly paralyze us. Our brains have a serious aversion to firing up projects when we can’t envision the final product.


It’s part of the reason why it’s hard to go to the gym today because the mental visual of that beach body six months from now is too murky.


That's why I enjoy helping folks make writing an easy process. Let’s make it infinitely easier than sticking to a new fitness plan.


Kick those hesitations to the curb and start writing rockstar sales emails that build relationships! Here are 10 tips I've pulled together from the thousands of outreach emails I have written and received.


Want to write a good sales email? Here are 5 Dos and 5 Don’ts


Do: Let quality research do the heavy-lifting for you


Understanding your target reader is key. I get tons of emails asking me to check out industrial-sized phone servers meant for huge companies.


One glance at my website, and I think it is pretty clear we’re good with a few iPhones.


The person who keeps contacting me about this is not only wasting their own time, but they’re single-handedly plummeting their own pitch-to-sale ratio.


Enough poor targeting, and even if you’re great at selling, your performance doesn’t look so hot.

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So what can you do? Sometimes it takes a little research, and you don’t even need to worry about selling—showing that you’re interested does all the heavy lifting for you.


I’ve gotten more clients without pitching at all. How?


Although I love writing, I am not a Karen-about-town for other people’s grammar. But, once I stumbled across a pretty significant typo on a site for satellite imagery tech.


I didn’t pitch anything—just emailed them to point it out—and it turned into an exciting project.


Another site I was reading built a really cool technology, but the thing that helped it really stand out was buried in copy that you had to scroll through for 5 minutes to find. I reached out and said, “Hey, you might benefit from pulling this feature out and screaming it from the rooftops closer to the top of this page.” Bingo.


We innately feel a bit off-kilter when we sense someone is trying to persuade us to do something. So sometimes, it helps to ask a question rather than dive into a pitch.


Now, I don’t suggest using this disingenuously—I never recommend wasting other peoples’ time if you’re looking to form a working relationship. But, if you read something intriguing the person has written about and have a follow-up question—go for it.


Learning more about what a person or company does isn’t a zero-sum game. There’s a lot to be learned and a lot of relationships you can build just by being curious.


Do: Let people know what you want them to do next


The thought of turning over 15 minutes of your time or scheduling another dang meeting is flat-out exhausting to most overworked professionals. Yet, tons of emails ask for it, and honestly, lots of sales training recommends it.

Use your "in" to start a conversation—not immediately demand an appointment.

Instead, try to start a conversation instead of demanding an appointment.


“Are you interested? Shoot me a reply; I’d love to answer your questions.”


“What’s your biggest roadblock when it comes to manufacturing?”

“On your site, you talk about working with vibranium: what have been your biggest challenges so far?”


Especially in this era of isolated remote offices, expressing a genuine interest in somebody’s work is a great way to connect.


Do: Disarm your reader by including an intriguing detail about them


If you’ve ever had a census worker come to your door, you’re probably familiar with these little “ins” they use to spark conversation.


They don’t immediately pile on questions about your income or fellow residents—they use a little skill called a “quick connect.”


These disarming nuggets range from noticing the Buffalo Bills flag waving from your second-story balcony or the award-winning rose bushes coloring your walkway.


By working these relatable details into the conversation, you’re more likely to engage rather than send them on their way.


I received one email recently that topped all the others. I honestly wish I needed the product this guy was selling, and I definitely plan to keep him in mind as my business evolves to that point.


What did it say? The email opened with:

Now, I am definitely not a closed book. I’ve got dozens of blog posts on my site. The About Larissa page on this very site says some cool stuff about me. (Some entrepreneurs seemingly balk at including anything interesting or “personal” about themselves on their site—I’ve gotten awesome clients just because they saw that I am from NYC or that I love the New Orleans Saints #WhoDatbut that’s a topic for a later post.)


A few quick seconds of recon and anybody trying to pitch me something can find something to a) praise or b) relate to or c) question.


If you’ve ever been on a date in your life, you know that these are typically great ways to connect with someone new. Guess what? The strategy also works in the business world.


I started working with a designer from a cold email once because she remarked that it must’ve been pretty weird to grow up in New York City and go to a college on sun-splashed shores of the Baywatch backdrop.


Now, you don’t want to focus entirely on small talk, but giving an indication—any indication—that you care a bit about who you’re talking to definitely adds some extra brownie points in your column.


Do: Showcase how your product or service helps them win


I get a lot of emails pitching technologies I’ve never heard of. While they might be able to help me, the sender doesn’t do themselves any favors by assuming I know what they’re talking about.


For example, one company recently contacted me pitching themselves as a “front-end (React, Angular, Vue.js. etc.), back-end (Ruby on Rails, Go, Python, PHP, .NET, etc.) software team.” While I know a bit about what this means and what I could get from it, the hard truth is—most people do not.


Another head-scratcher? “...as an End-to-End Solutions Provider...”



Yes, “short” is good, but “short and sweet” is better.


When going short, don’t cut out the honey—the part that sticks.


The honey is the magic. It’s where you break away from the pedantic dictionary definition of your line of business and let potential customers know the real value: the brilliant way you can help them improve, grow, or simplify how they do things.


I recently received this great email focused almost exclusively on the honey—the true value they can provide me.


Hey, that sounds great!


The email didn’t distract me at all with any mumbo-jumbo but drilled right down to the value they provide business owners like me. I might not need what this company is offering right now, but I have a solid grasp of how it can help my company flourish if I’m ready for something like that in the future.


Do: Use a real person’s name vs. “The Better Company Team”


Maybe it is just me, but emails signed by a generalized team rub me the wrong way. Whenever possible, sign the email with a real name—an actual person that works at your company.


News flash: it doesn’t necessarily have to be the person that is writing the email. While it’s important to transition the conversation over to the real person once you get the conversation going, pick a go-to individual that any team member can sign with. It’s a little thing that makes your outreach feel a little bit more personable.


Don’t: Keep it so short that you leave out the human touch


I’m all for conciseness, but some people swing this club so hard that they forget to sound human. The uncanny valley is real—we humans have a real aversion to things that sound a little too fake. Wander a little too close to this invisible line, and your email goes right to the bin.

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Don’t be afraid to be a little spirited—sprinkle in some conversational elements; even silly things like “Here we go—another Monday!” in a Monday morning email proves you’re not just spamming the same message all week long.


Avoid coming off too obvious that it’s a cut and paste job—this can make the reader feel uneasy. Even if they’re interested in what you’re selling, overly robotic gives the impression that their reply might get the same disingenuous treatment. Emails that are too canned risk leaving potential customers with a sour impression of your customer service level.


While you definitely have to weigh the pros and cons of a mass-messaging strategy, a few thoughtful and personable tweaks can go a long way.


Don’t: Cast a net too wide


This isn’t Wicked Tuna: if you’re hawking a niche or specialized offering, emailing every Tom, Dick, and Harry with a particular job title on LinkedIn is a questionable bet.


For example, instead of assuming they’re using a certain platform for web design and pitting your offering against it, take four seconds to find out what they do use. Don’t just cross your fingers and hope your comparison pitch will land.


In a lot of cases, you don’t even need to ask.


Say you sell something that syncs up with a specific website design platform or email provider—or competes with one—how can you find out what tool the company currently uses?


Here are 3 ways that take less than a minute each:

  • Sign up for their email list: You’ll likely receive a confirmation email, which most of the time indicates the email partner in the footer.

  • Got Google Chrome? Go to their site and view the source code. If you’re not a tech-head, don’t be intimidated by the code wall. You can do a quick CTRL+F for “MailChimp” for example, and see a few lines of code that indicate my site uses MailChimp plugins. At the very top, you can even see it’s built on Wix.

  • Also, don’t be afraid of the cobwebs of a site—the gnarly pages nobody dares visit...duh duh duh….like the Privacy Policy page. These days, they’re loaded with technical intel: most specifically call out which third-party cookies are used by the site backend.

how-to-view-page-source
Targeting users of a certain tech? With a few quick tricks you can pinpoint your target audience.

A few quick clicks and you’re on your way to learning a little more about your target customer, so you can really hone your messaging.


Don’t: Just use a template


What to say in a sales pitch

What to say on a resume

What questions to ask in an interview


There are millions of websites that share templates for just about anything. While you might think you’ve found one on page 35 of Google that nobody has seen yet—think again.


We all know when we’re reading a template. The tone is cheesily upbeat (even I with this natural trait can see through it 😉), or it’s far too stereotypically dull.


Here’s an everyday example: Just think how many text messages you get every month telling you that you’ve successfully updated your billing address or payment method. They all sound exactly the same.


Don’t fall for the “template trap”—the ill-fated siren song telling you that everyone does it this way, so you should too.


Make it a little fun, make it a little exciting—and hey, as I harp on in almost every single one of these posts—don’t be afraid to be yourself.


Yes—you, the real you.


You are far more interesting than any email template on the web, so don’t be afraid to be a human in your copy.


Don’t: Forget to test your email sequences


bad-sales-sequence
A disorganized email series is like shoving your customer into an elevator with all the buttons pushed.

As long as you mind some of the above advice, there’s absolutely nothing wrong with creating a sales sequence in advance.


Hey, we’ve all got to save time somehow!


It’s called a drip sequence—a series of emails you write all at once and then instruct your email service to automatically plop them into email boxes at predetermined intervals. So you might set up five emails to go out on five consecutive Thursdays. You can get pretty crafty with these—arrange different ones to go out if the recipient has or has not opened the previous email, set one to go out if they click a link in one of your emails, etc.


But, you’ve got to test them out.


You might have some of these in your own inbox, the final declarative goodbye— “Since you haven’t reached out yet, I’ll assume we are not a fit.”



Finally, they vow to leave you be! But come next week, and you’re somehow re-enrolled in the inescapable clench of automation.


They’re back to email #1, pleading for you to check out their product demo.


It’s like stepping into the elevator of your reader’s inbox and pressing all of the buttons at once—here we go again, and the chance for escape is not coming anytime soon.


So be sure to test your automated drip sequences every now and again. Make sure they’re firing off in the desired order and aren’t trapping leads that are a bad fit in an infinite pitch loop.


Don’t: Be afraid to be casual


If this isn’t your first time on the Jargon Gist blog, you know what’s coming next. In fact, say it with me: take off the corporate robot helmet—it’s ok to be casual!


Many of us are caught in this inescapable web of outdated professionalism. From school needling us to write in a serious tone and our first jobs dictating “workplace words.”


When it’s time to write for work, most of us immediately fall back on trying to sound like an overstuffed grey suit spouting words like “solutions provider” and “revolutionary” and “purpose-driven” because hey, it’s business time.


Consult with a top-hatted and time-traveling 17th-century shoppeowner, and he’d send you to the guillotine for using “you” instead of “thou.” Suffice to say, I think we can all loosen the necktie on stifling workplace-speak, even if just a little bit.


I once split-tested an email with a client (meaning, we experimented with a bunch) that basically said this:

We played it against the old way—a droll introspection into the company’s manufacturing processes. Even if you’re in l-o-v-e with that subject matter, that doesn’t mean you’re always in the mood to read another jargon-plagued deep-dive, but you do want to know how you can do your job better. So, out with it! Let the reader see and feel how you can help them.


After we started sending that email, they shipped out 15-20 samples in the first week and closed three new contracts from the refreshed outreach (which is a big deal for their line of work).


In case you were wondering, we got precisely zero replies back on the “more professional” version.


Don’t be afraid of ‘casual’ and don’t be afraid of ‘helpful.’ In the sea of pretentious corporate-speak, sometimes sounding like a real person, someone who genuinely wants to help, not sell, is the golden ticket.


It's time to pen your very own rockstar sales email!


No matter how many layers of screens are between you and the customer, B2B is primarily a people business.


People want to work with people they enjoy working with, people who care, and people who aren’t afraid to go the extra mile (which in a lot of cases is just the few extra feet your competitors have opted against in favor of “efficiency.”)


It’s a paradox that when it’s business time, many of us need frequent reminders to act compassionate, be ourselves, and express interest in others. I think the mindset evolved from the old days—you had no choice but to work at the one factory in town, and yes, most people did have to pretend to care.


But these days, every industry is at your fingertips, and nearly every impassioned hobby has a correlated career path, giving everyone a remarkable opportunity to work in a field they are actually passionate about.


Hopefully, you’ve found yours and are able to infuse some of that unbridled energy into each and every sales connection.







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