Prospecting Small Business Owners: Empathy-Driven Strategies

Prospecting Small Business Owners: Empathy-Driven Strategies



Tyler Carlson


January 18, 2024

There's a lot of content that explains the best strategies and channels to prospect small business owners, but few of them delve deeply into the importance of understanding their challenges and daily lives.

I want to share with you my encounter with Audrey, the owner of Mr. Empanada in Tampa, and how I learned that empathy can be a game-changer in how we approach sales.

This post explores the importance of empathy in sales, how to prospect local business owners, and tips to improve your approach.


  • How to Prospect Small Business Owners
  • Relationship Building in Sales
  • Top Tools for Small Business Prospecting
  • Conclusion: Integrating Empathy into Your Sales Strategy

How to Prospect Small Business Owners

Adopting a Benefit-Oriented Sales Approach

I remember the day I visited Audrey, the founder of Mr. Empanada, a local business in Tampa. Her desk was a testament to a busy life – covered in a chaotic assortment of papers and various items, a common sight for business owners.

Desk of a local business owner

This scene really put into perspective the overwhelming amount of tasks business owners juggle daily.

As we talked, I noticed Audrey seemed a bit tense, probably wondering about the purpose of my visit. I assured her I was there not to sell, but to genuinely understand her journey with Mr. Empanada and how she's been carving out opportunities for herself.

During our conversation, Audrey received a phone call. The caller claimed to be from DoorDash, but she was skeptical, fearing it might be a scam.

This moment was eye-opening for me. It underscored how salespeople can often feel like intruders in the already chaotic lives of business owners.

Witnessing Audrey’s cautious response made me more understanding when my own outreach didn't receive immediate replies.

This experience led to an epiphany: business owners aren't ignoring us, they're simply overwhelmed. That's why I advocate for what I call a Benefit-Oriented Approach.

It's not sufficient to claim empathy; we must actively seek ways to alleviate some of their daily burdens through what we offer.

Audrey's story is a powerful reminder. Successful sales are not just about closing a deal, they're grounded in genuine understanding, empathy, and offering tangible value.

How do I reach local business owners?

It's not just about spamming emails or blowing up their phones. These folks are usually super busy, running their shops and all.

While tools like social media platforms, email, phone calls, and attending networking events are effective, it's crucial to choose channels and platforms that cater specifically to small business owners.

Less than 10% of local business owners are active on LinkedIn, a primary channel and data source for B2B sales.

Yeah, platforms like are cool for the big business crowd, but for your local shop owner? Not so much. It's estimated that at least 60% of small businesses aren't present on these platforms.

So, when you're reaching out, keep it real and personal. Show them what's in it for them, and always keep it professional, but remember: it's all about picking the right spot to hit them up!

How do you prospect a small business?

A lot of people make the rookie mistake of getting lost in endless Google searches and drowning in spreadsheets.

But here's the deal: U.S. brick-and-mortar stores are shelling out a whopping $1.6 trillion on vendors yearly. But Most B2B sales tools aren't even made with them in mind.

We've got over 400,000 sales pros in the U.S. trying to reach local businesses using tools meant for the big league or doing the old-school door-to-door thing. And small businesses? They end up dealing with a ton of junk mail and annoying call centers.

The real game-changer? Work smarter, not harder. Pick the right platforms to find these small business owners and put your energy into sharpening your sales game.

Imagine having the data on every local business in the U.S. and Canada – that's over 11 million businesses at your fingertips. And it's not just about data, we're talking AI-powered email and social media tools that make your messages pop.

With Resquared, you'll get templates and sequences that are all about the numbers, plus top-notch training and support.

The team? They're like your personal experts, ready to guide you at each step. Curious to see how this can revolutionize your prospecting game? Dive into our product and see the magic for yourself!

What are the 5 most common prospecting methods?

When discussing the most common five prospecting methods, people typically refer to these approaches:

  • Warm Calling: This isn't your average cold call. It's about doing your homework and checking out your prospect's social media and website to find common ground. Then, hit them with the Double Whammy - a call followed by another touch-point, like an email or a text.
  • Referrals: Start with who you know. Your current contacts or clients might just have the perfect intro to your next big prospect.
  • Content Marketing: Think of it as being helpful rather than sales. Share smart, useful info to build trust and show your expertise. Networking: Figure out why you're networking and who you need to connect with. Then get out there and start building those relationships.
  • Email Marketing: Emails are like mini billboards in your prospect's inbox. Make the first ten words count to grab their attention.

But that's not all, make sure you stick around to catch the best strategies!

Relationship Building in Sales

Have you ever considered your sales technique in light of Hollywood charm? It might seem unusual, but it's a useful analogy.

When reaching out to potential clients, ask yourself: are you exuding George Clooney's charm or a creeper?

Clooney or Creeper - Prospecting Approach

Think of it this way: pitching your service in the first email can be akin to asking for a date without knowing if the other person is interested. Imagine randomly asking someone out – it's awkward and unwelcome, right?

So, rather than jumping in with:

"Hey, can we schedule a meeting Friday at 11 AM to discuss how my product can boost your sales?"

Opt for a more engaging approach:

"Hey, Leah! We've assisted other businesses in X industry to overcome Y challenge and achieve Z. Are you facing similar hurdles? I'd love to chat and explore how we might help."

This method is less about the hard sell and more about sparking a conversation and showing genuine interest in the recipient's challenges and needs.

To understand why this approach is effective, picture this scenario: You're at a Sales Convention, and someone claims they have the cure for Ebola. Your first thought?

"Interesting, but how does it relate to me?"

The same principle applies in sales. If your product or service doesn't clearly address the listener's specific needs or problems, it won’t hold their interest.

That's why it’s essential to identify and communicate the unique value of what you're offering.

The goal is to transition from a pushy sales tactic to a more curious and empathetic approach, one that's truly aligned with what the potential customer needs and seeks.

Top Tools for Small Business Prospecting

Know Your Audience - It's All About Geography and Business Type!

Identifying and targeting your audience is like hitting the bullseye in darts – it's all about precision. And geography and business type are your secret weapons!

Forget about those bland "Florida Business Updates". We're talking about something juicier, like "Downtown Tampa Retail Insights." See the difference? By getting specific, you grab the attention of the right folks in no time.

Oh, and don't use "Restaurant Owners." That's as broad as a Texas highway. What you need is the good stuff: "South Tampa Pizza Shop Updates." That's how you make an impact!

Email Prospecting Hacks

1. Spice Up That Subject Line

As you already saw, instead of going with "Business Opportunity”,  go for something like "Opportunity for Local Coffee Shops." Make it specific, so small business owners can't resist clicking.

2. Say Hi with Their Name

Wanna build some rapport? Use their first name in the greeting.

Did you know saying someone's name releases happy chemicals in their brain? Yup, it's a neat trick to make a connection and get a positive response.

3. Drop Their Business Name

Make it personal by mentioning their business name. Show 'em you've done your homework and crafted this email just for them.

4. Get Personal with Their Business

Stand out by dropping compliments or specific details about their business. It could be their killer products or a unique feature. It shows you've taken the time to snoop around (in a good way).

In Resquared, for instance, you've got AI Snippets at your service. Just add the [ai_snippets] tag, and it will instantly upgrade with personalized content, designed to the specific business characteristics.

5. Why You're a Match

No one-size-fits-all here. Explain why your offer suits their needs. If you're into real estate, spill the beans on property perks. If you're a marketing specialist, talk about services they don't have on their site.

6. No Flyers Attached (at First)

Flyers are cool but don't slap 'em in your first email - avoid spam!

7. Go Plain Text

Fancy formatting and attachments? Not for your first email. Keep it simple with plain-text emails. Spam filters hate the fancy stuff.

Plus, short messages get 10x more replies.

8. Master the Follow-Up

Success needs a dash of persistence. Don't rely on one email. Mix it up with calls, Facebook messages, and emails. It usually takes around 8 touches to seal the deal.

Bonus: Sample Email Template

Subject line:

Opportunity for [Business Type] in [Geography]


Opportunity for [Business Name] in [Geography]


  • Space Available for Nail Salons in Santa Clarita
  • Opportunity for Diana’s Beauty in Santa Clarita


Hi! I'm working with a Santa Clarita shopping center right next to the Metrolink and have a space available for a nail salon. After reading about [business_name], I think you might be a great fit! Do you have any plans to relocate or expand? Let me know and I can send you a flyer or set up a tour.


[Your Name]


Hi! I have an opportunity for businesses looking to expand their online presence. After learning more about [business_name], I believe we could be a great fit for your online expansion.

As a specialist in creating complete websites and e-commerce solutions, I've helped businesses like yours thrive in the digital world. If you're interested, I'd be happy to discuss the details and provide you with a personalized plan to get started.


[Your Name]


Here are four solid reasons to use Facebook to connect with small business owners:

  1. Hyper-Local Targeting: Facebook's got the magic touch when it comes to reaching folks in specific neighborhoods. Want to target that trendy coffee shop in your area? You got it!
  2. Gatekeeper Bypass: No more gatekeeper games! With Facebook messaging, you can slide right into the DMs of decision-makers. No more getting lost in email or blocked by gatekeepers.
  3. Direct Line to Decision Makers: Unlike email, Facebook messaging feels like a chat with a buddy. Plus, business owners keep an eye on their response time, so you're in their spotlight!
  4. Low Competition: Let's face it, your email inbox is probably drowning in sales pitches. But what about Facebook? It's like the Wild West out there, and fewer are prospecting on Facebook. Your message will stand out!

If you're all in on Facebook, it's time to unlock the secrets of Facebook messaging:

  • Personalization Rules: Be you! Tailor your messages to the recipient's interests. Did they post about their awesome cafe? Mention it! Keep it short for maximum impact.
  • Timing is Everything: Hit them up during business hours for a timely response. No one likes late-night pitches.
  • Spam Filter Hack: Don't flood their inbox. Too many messages too soon can trigger Facebook's spam filters. Space it out.
  • Give Value: Share success stories about how you helped other businesses.


Ready to conquer Instagram and connect with qualified leads? Here's your game plan:

Head to the "Discover" page by tapping the magnifying glass at the bottom. Time to explore!

Click on the map icon (it looks like a location pin) in the top-right corner. You're in map mode now.

Map Mode - Instagram

You'll see a bunch of popular local businesses on your screen. Check out those categories—they're gold!

Got a specific craving, like cafes? Type it in the search bar at the top. Find a place you like and dive into their profile.

Once you're in, shoot a direct message to the business owner.

Don't snooze on Facebook and Instagram. They're your golden tickets to connect with small biz owners and supercharge your sales game!

Conclusion: Integrating Empathy into Your Sales Strategy

Before thinking about any strategy, it’s important to get to know the small business owners you’re trying to reach.

We sell to them all day, but we really don’t know who they are, what their daily routine looks like, and what's annoying for them. It's important to understand their challenges and how your product or service can help.

This way, any email, message, or call will start by bringing value and initiating a conversation, instead of 'spam selling'. You have the knowledge, strategies, channels, and tools, along with plenty of tips.

Just remember, never lose sight of the individuals behind the businesses you seek to serve. Each prospect has a unique story, and by listening and empathizing, you can become the trusted partner they've been searching for.

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