The Trick Behind Selling to Small Business

Jeff Yablon
Business Change and Business Process
3 min readSep 21, 2017

Selling is hard. Selling to Small Business is harder. Wait, check that; selling to small business is A LOT harder. It was true when I wrote about selling to small business in 2011, and it’s just as true now.

In fact, selling to small business just keeps getting harder, and it was hard way before that 2011 article — which tells about something that happened in 1998 and wasn’t exactly news even then.

Small business really is different than larger business

And as much as I lean toward seeing similarities in situations, small business really is different than larger business.

Even more than “cracking the millennials code“, cracking the small business code has puzzled sales and marketing types forever. Let’s start with a quick recap; small business is special because small business owners:

  • plan mostly for the short term
  • seek value but buy on price
  • wish to feel like they’re using something cool
  • want to be spoken to like a partner (not a target)
  • and yes, will keep buying from you forever as long as you take care of all of the above

Small businesses will not buy from you unless they trust you, and earning that trust is hard

While the last three points can be applied to pretty much anyone — albeit in different ways — the first two truly separate small business from larger business and Enterprise customers. Small businesses will not buy from you unless they trust you, and earning that trust is hard.

When I started thinking about this the other day I dug around a bit and found that the article that inspired my 2011 musings still ranked highly with Google search for “selling to small business”. That got me digging a bit more; I found that this topic hasn’t really evolved since 2011. I did come up with this article from back then, though; it’s an interesting read. But despite the plethora of tips that so-called “experts” people cobble together on the topic, not much has changed.

Selling to Small Business

The issue boils down to that trust thing. And I still had to dig back to — yikes, 2012 — in search results. Which, if you’re selling to small business, may actually be a good thing.

Why? Because the very idea of selling to small business seems to have been pretty much abandoned. So let’s recast, 2012 style. Small business wants:

  1. Value
  2. Follow-through
  3. Help … right now
  4. Referrals and a sense of community
  5. Viable paths to growth
  6. A real relationship

Think about how large business deals with small business. Ask yourself how many of those points get hit. Bleak, right?

The online world has fostered an entire generation of businesses that act like they’re huge even when they aren’t

Now ask yourself how many of those non-connections you have with e-businesses (large or small). Just as bleak. The online world has fostered an entire generation of businesses that act like they’re huge even when they aren’t.

Selling to small business comes back to relationships. Period.

And there’s an opening there if you have the moxie to head toward it. Need some help navigating?

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