Why Personalized Outreach Is Key to Closing Deals with SMBs

Every. Single. Day. I open my inbox and see outreach emails that are just… a waste of my time. 

Most of the emails are just generic templates with my name or product shoved in there and a half-assed attempt at “personalization”. 

These worked a decade ago when automated email marketing was the new kid on the block. But now SMBs expect a lot more from personalized outreach. 

So, with every sales rep now using (some form of) personalized outreach, how do you stand out from the pack?

It’s all about going beyond the generic template to earn trust, grab attention and use the right tools to sell at scale. In this article, I’m going to teach you how to do just that 👇 

What is Personalized Outreach in Sales?

Personalized outreach is the art of using customer information to create a unique experience that targets their specific pain points and needs. It uses tactics like audience segmentation, tailored emails and in-depth research to craft hyper-personalized messages to grab a prospect’s attention. 

Let’s cut to the chase. 

We’ve all had those “personalized” emails land in our inboxes. You know the ones I’m talking about, where <FIRST NAME> tags are plopped at the top of the message as some lazy attempt at personalization. For me, truly personalized outreach in sales is when the SDR scratches at my itch. The email makes me sit up and think… holy shit, this rep really understands my problem or what I’m trying to do here. 

A lot of sales reps just… get lazy. And in return, they don’t get many bites from prospects. 

When I think about personalized outreach, my mind always goes to the massive outbound experiment Shane Snow of Contently, and Jon Youshaei of Every Vowel did circa 2014. The guys sent 1,000 cold emails out to senior execs at big orgs to see who would bite, and each one had different subject lines, email lengths and messaging. 

The experiment had some not-so-surprising results around personalization. Not only did the pair get a 45.5 percent open rate, but the main takeaway was also that personalization pays off. The more research Jon and Shane did into the person they emailed, the better the result. Just check out this email Shane sent to Adam Grant— one of the busiest people in academia:

Subject: Shook your hand at NextJump, would love your advice


Fantastic presentation at NextJump yesterday! I was thrilled to shake your hand and say “thanks” right before you ran out. I was also happy to see your book hit the Print+Ebook bestseller list in the Times Book Review last week. The world needs this message.

I feel apprehensive asking you this, since I know you have plenty of opportunities to give already, but I wanted to know if, when the frenzy dissipates, you would be willing to coach me a bit on the work I’m doing for my first book? I just signed an exciting deal with HarperCollins (my editor, Hollis Heimbouch, works with Clayton Christensen and Jim Collins) for a book that I’m hoping will help a LOT of people. (It’s inspired, in fact, by XXXpersonal storyXXX.)

I’d love to tell you more about the book, which is provisionally titled Smartcuts, and pick your brain for one of my chapters. But most of all, I’d be delighted to get your advice on managing the whole process as well as you have. Perhaps we can grab a few minutes at your office or here in New York sometime?

Best wishes,


Now, it takes a shitload of time for this email to come together. Not only did Shane have to meet Adam, but he researched his books and recent events. He used those chunks of information to hyper-personalize the email and weave in his own ask: to grab a few minutes on his busy calendar. 

A big ask? Yeah. 

Did it work? You bet. 

Now imagine if every email that left your inbox was this personalized. Can you imagine what your pipeline would look like?

That’s the power of personalized outreach. 

Why Personalized Outreach is Key to Closing Deals with SMBs

SMBs are a different monster compared to Enterprise companies. 

Personalization outreach with SMBs is so much more than adding a prospect’s name or company to your email. You have to make an effort and do your research. Their budgets are tighter. Their needs are more urgent. A lot of these companies are trying to scale against fierce competition and dog-eat-dog industries. A lame, generic template just ain’t going to cut it if you want to book a meeting on their calendar. 

But personalized outreach can help you stand out from competitors. Think about it. If SMBs from your closest competitors are pumping out semi-personalized messages (like the fill-in-the-tag-here emails we just talked about), they’re fighting an uphill battle. An inbox full of emails mentioning just the prospect’s company name all of a sudden look really generic when they’re all stacked next to each other. 

Personalized outreach helps you go beyond all that. When your competitors rely on mentioning a name to connect with leads, you can dig into prospect problems and talk to them about stuff they care about. 

Oh, and did I mention personalized outreach is also one of the best ways to build trust with potential customers? 

Believe me, I know. Let me explain…  

How Personalization Can Build Trust Early and Create Loyal Partnerships

Nobody will ever buy your product if they don’t trust you. 

Most sales teams know that SMBs can be skeptical, especially if you’re selling something new (or are a new company in general). It might not have anything to do with you, but if an SMB has had a bad experience in the past, it’s another hurdle your sales team needs to jump over. To win their trust and credibility, you must establish yourself as an expert in your industry and be upfront about what benefits you bring to the table. 

I hit this problem when I first launched our outsourced sales service. Think about it, as a company, we had nothing. No credibility, no references, no testimonial. Just my blood, sweat, tears, and sheer want for other startups to pay us for selling their product in their name. 

That takes a ton of trust that is really hard to build. I believe this happens in three steps: 

  • The prospect must trust you as a person and believe the human they’re interacting with is legit
  • Then, you must build trust in the service or solution you’re selling
  • Finally, building trust in the company so prospects know when they hand over their hard-earned cash, it’s in good hands

All of this is almost impossible to achieve if you don’t personalize sales outreach right out of the gate. I’m talking about small gestures like sending prospects helpful content like blog posts, whitepapers, and case studies. Or it could be something more substantial, like picking up the phone and telling them exactly what your company can do for them—and how you’re going to do it. 

Hear about how I leveraged this exact strategy to earn a customer’s trust—and keep it 👇 

YouTube Embed

Want to Personalize Your Outreach? Get Ready to Face These Challenges

If personalized outreach was easy, everyone would be doing it, right? Before diving into your next personalized outreach campaign, make sure you’re aware of the challenges you’ll face.

1. Prospects (By Default) Don’t Trust Cold Outreach

Those personalized emails you spent an hour writing? Or the video message you’ve just finished editing? Don’t be surprised if, even after you send a message over, a prospect still ghosts you. That’s because most outreach messages they get are pulled straight from shitty, generic email templates and push a hard sell right out of the gate.

Believe me, a prospect can smell a sales development representative that’s looking to fill a sales quota from a mile away. 

How to solve this: Get off on the right foot. Actually do some research into what prospect the problem has and what they need in a solution. If you don’t have time to research each prospect thoroughly, invest in lead generation or sales tools that make it easier. Forget the other stuff and get back to basics: solving your prospect’s problem. 

2. Don’t Let Your Lead Generation Data… Let You Down

The bread and butter of a successful prospecting strategy is data. But when 55 percent of companies say they lack trust in their data assets—we’ve got a big problem 😳

It gets worse. Around 32 percent of companies don’t just lack trust in their data—they think it’s inaccurate. Now for the worst part. If the data you use for personalized outreach is wrong, it’s the quickest way to earn a one-way ticket to the trash can. Calling a prospect the wrong name or talking about a company that’s… not theirs? Yikes.  

How to solve this: Invest in lead enrichment and tools that target data decay. Keep your customer profile information up-to-date and check relevant information like names, company size, job titles, and geography regularly. The best way to keep on top of this is with a sales CRM, and you can even put some of these tasks on autopilot to save time. 

3. Using AI to Personalize Messages Can Muddy the (Ethical) Waters

Sales tools like predictive analytics and chatbots can speed up the outreach process and quickly gather data to personalize your message. But it comes with some ethical considerations to think about. For example, AI tools can scan a prospect’s social media channels and even spot clues in a LinkedIn post, like the types of books they’re reading, to help you personalize outreach. 

This level of insight can help you craft super personalized messages and fast-track the prospecting process. But is it ethical? Well, it’s a gray area. 

How to solve this: Use AI-powered personalization tools on a case-by-case basis. It can really help personalize social media outreach and find out stuff about a prospect that would take you days. But don’t snoop through their LinkedIn profile too much, otherwise this sort of outreach can quickly border on creepy. 

Now we’ve talked about the biggest roadblocks to personalized outreach, let’s take a look at how to create a strategy that works 👇 

4 Personalized Outreach Strategies for SMBs

If you want to close deals with SMBs, personalized outreach is key. In a world where we’re constantly bombarded with marketing messages, personalized outreach stands out. It shows you’ve done your homework and care about the recipient’s needs. Here are some strategies to help you personalize your outreach and close more deals.

1. Segment Your Audience (Get Niche!)

Segmentation is the oldest trick in the personalization book and should be the first stop when you create an outreach campaign. 

Break your target audience into smaller groups based on demographics, interests, job descriptions, or other factors like budget, sales cycle, or pain points. Once these groups are separated, creating content and messaging that speaks directly to their needs is easier.

Now, audience segmentation can be as basic or complex as you want it to be. At Close, we split prospects off depending on all kinds of conditions, from how big their company is to if they have signed up for a free trial of our product. 

As soon as the groups are segmented or updated inside Close, it’s immediately pushed to our marketing automation tool. Then, we customize the email sequences sent to them based on their behavior and actions so they’re hyper-relevant and personalized.

2. Personalize Subject Lines, Copy, and Offers to the SMB’s needs

One of the biggest mistakes salespeople make with cold email outreach is sending irrelevant messages. 

When you’re reaching out to SMBs, it’s important to focus on what they care about—not you. A personalized subject line or adding in a relevant case study can really light a fire under email reply and response rates. Just make sure whatever you add, from screenshots to call to actions, speak directly to the prospect’s needs. 

Here’s how I do it. 

  • Build your outreach around what the prospect is up to. Social media channels and company announcements are total goldmines for tracking what high-value prospects are up to. If time is tight, create qualified lead lists based on specific criteria and tailor them to your personalized outreach criteria. A CRM comes in handy here. For example, you can add custom fields in Close to segment leads and create outreach campaigns at scale. 
  • Personalize every email. Yes, I’m repeating myself, but personalized outreach must go beyond just mentioning a prospect’s name or company. I use the TextExpander tool with Close outreach templates to insert pre-written text snippets into my outreach emails. This adds in relevant, personalized copy that’s industry-specific or tied to a specific problem the prospect might be facing. 

Take that last point. Just say a food and beverage prospect in my pipeline is a good fit for Close—they need a new CRM and have the budget to splurge on some of our more advanced features like Sequences and Custom Activities. To reach out to the prospect, I’ll pull a template from the Close library and then add a snippet to include a case study (like this one) to show them how we helped a similar company boost its sales. 

It’s a lot more effective than just asking them to jump on a call or sign up for a demo, don’t ya think?

3. Don’t Be Afraid To Test Out Video Messages

There’s one thing you can’t fake, and that’s a tailored video message to a prospect. 

The best SDRs are now using video to personalize outreach with prospects. In fact, one report by Vidyard found video for sales prospecting has jumped by 93 per cent year over year. More importantly, the average click-to-open rate is 16x higher and this type of personalized outreach also increases conversion rates. 

Now, these videos still have to cover the basics, like the prospect’s interests, pain points, industry, and needs. But if you use them in the right way, they can free up your schedule and still get great results. Instead of spending an hour talking to a prospect about your product, you can pre-record a pitch and send it over to them to watch when they get a chance (which is super helpful if they are in a different timezone. 

Video messages also help give your sales reps a competitive advantage. Only 43.8 percent of sales teams are using video campaigns to personalize outreach, so it’s a killer way to stand out in your prospect’s inbox. 

Don’t take my word for it. Hear what Bethany Stachenfeld, Co-Founder and CEO of SendSpark, recently had to say about video outreach during a conversation with our very own Sr. Partnerships Manager at Close, James Urie:

YouTube Embed

Pro-tip: We’ve written a lot on how teams can use video to close more deals. Check out this guide to video prospecting and this piece about video personalization to get started. 

4. Follow Up, Follow Up…. Follow Up! 

In sales, following up is really where the big wins happen. 


Well, a lot of SDRs throw in the towel way too early. My message to our sales team is always to stop making up stories about what they think prospects want and instead pick up the phone and ask them. They tell themselves the prospect isn’t interested anymore or that they don’t like the product and move on to the next person in their pipeline. 

Here’s the thing. A lot of sales reps will hit it off with a prospect. A great initial call and some positive responses to early emails are all good signs. But they give up if they don’t hear back after a follow-up email or two. 

But when you are closing a deal with an SMB, it’s all about building relationships and providing value. And yes, that includes following up multiple times if you need to earn their trust and prove that you give a shit. By taking a customer-centric approach and personalizing your outreach, you establish credibility and prove that you want to help them. 

Remember, personalizing your outreach to SMBs won’t just help you gain trust or fill a pipeline—it’s a shortcut to close more deals. 

Steli Efti
Steli is the CEO of Close.com, a sales CRM built for the future of sales.

Leave a Comment