🚫 Top 10 mistakes selling to SMB owners like me

I own ~40 restaurants, have sat through hundreds of pitches, and have spent millions on new software and hardware solutions. Here are the biggest mistakes I see over and over again.

Selling to small and medium-sized business (SMB) owners can be tough. With limited time and resources, SMB owners are bombarded with sales pitches daily. If you want to get their attention and close the deal, you need to understand what works and what doesn’t. I own about 40 restaurants, have sat through countless pitches, and have spent millions on new software and hardware solutions. Here are the biggest mistakes I see over and over again when selling to SMB owners:

1. Avoid Cold Emails and LinkedIn Messages

Don’t waste your time sending me cold emails or LinkedIn messages asking for a meeting or sharing product demos. I won’t read them. Instead, get a warm introduction from someone in the industry or an existing connection. A personal recommendation is far more valuable than a perfect pitch. If a cold call is necessary, leave a short voicemail. If you don’t, I’ll likely block your number.

2. Don’t Call My Employees

Never call my employees. This wastes everyone’s time. You need to speak directly to a decision-maker - usually the owner or department heads. Department heads are often working on specific initiatives and are open to exploring new solutions.

3. Scrub the Free Database of Contacts

You can access contact information for major U.S. franchised systems in the FDDS (Franchise Disclosure Document). This free database can provide valuable leads, including names and phone numbers, to help you reach the right people faster.

DFI Franchise Search

4. Get to the Point Quickly

You have 20 seconds to grab my attention. I’m busy, so don’t start with a lengthy pitch about how you’re going to "disrupt" my industry. Instead, explain what process or system your product improves and why I should care right away.

5. Skip the Overblown Promises

I’m skeptical of inflated promises about revenue growth or cost reduction. I expect less than half of what you claim to come through as actual savings. Instead, focus on defining a short-term success metric and hitting it, which will help me feel more comfortable rolling out your solution across my locations.

6. Offer a Low-Risk Trial Instead of a Big Deal

If you’re not an established name, don’t ask me to commit to signing up all my locations. Instead, offer a trial with a single location and short-term commitment. If your solution works, we’ll continue using it.

7. Keep Onboarding Simple and Quick

If your onboarding process is complicated or takes longer than 10 minutes, we won’t bother with it. My team is busy, and we need tools that are easy to set up and integrate quickly.

8. Provide Easy Integration with Our Critical Systems

Our point-of-sale (POS) system is the central hub of operations. If your product doesn’t easily integrate with systems like Toast, Aloha, Square, or Lightspeed, it’s a dealbreaker. Make sure your product integrates smoothly with critical SMB systems to reduce friction.

9. Involve Other Stakeholders Early

Once I’m interested, I need to get buy-in from other stakeholders in my organization, especially the GM or Head of Operations. If they don’t like what they see, the deal won’t happen.

10. Make It Easy to Say “Yes”

If you’ve made it this far, don’t complicate the closing process. Send me a simple, easy-to-read, mobile-friendly document with clear terms that I can sign directly from my phone. The best sales teams close deals while we’re still on the phone.

If you’re selling to SMB owners, follow these tips, and you’ll increase your chances of success. Want to discuss your closing process or documents? Just email me.

If you are selling to SMB owners and want me to take a look at your closing process and documents, just email me.

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