If you’re going to sell to small and medium-sized businesses, you have to do it as an intentional part of your strategy, and tailor not just your pricing but your entire approach, which might include your process, product, training and support. 

SMB is a segment in its own right; to be successful selling to this audience, you need to remove barriers, understand why and how they buy, and adopt the right mindset to ensure success with this market.  

With 30.7 million small businesses in the U.S. alone, the small business space represents a tremendous market opportunity for most brands and startup companies. However, just because it is a massive market does not mean it’s an easy market in which to be successful.

After spending the better part of a decade serving SMB customers, here are five things I’ve learned: 

1. If you’re going to sell to SMB, you need to go “all in.” 

The SMB market is not one you can half-heartedly enter, and 90 percent of brands struggle to identify and connect with actual small business decision-makers. One of the biggest misunderstandings is the idea that small equals “simple.” 

The reality is, SMBs have complex and nuanced needs, along with budget and cash flow constraints that force sellers to be creative and savvy. Small businesses aren’t just looking for a “lite” version of your enterprise product. To be successful with SMBs, you must really understand the audience and create value. While a little bit of effort can yield big gains in some markets, if you don’t make big shifts in your product, process and approach, you are unlikely to get much from your SMB effort at all.

This may mean changes to the way you package, price and sell. For example, while SMBs are happy to experiment and give new products a chance, long-term and binding contracts with heavy cancellation fees can be a deal breaker. Similarly, companies that are used to charging for implementation and training may need to make changes to eliminate those barriers to adoption and use.

2. Create value beyond your product. 

Compared to typical enterprise buyers, SMB employees wear a ton of hats, whether it’s a CEO who also runs accounting, or a sales professional who also manages the website. Small business buyers are passionate about what they sell, but they may not always be tech savvy, nor have functional expertise in all the areas of the business they are responsible for. 

This is important to understand because selling a product like marketing automation to a career marketer with 10 years experience is a very different experience than selling marketing automation to an SMB CEO who is responsible for marketing, but has no experience in it. 

Try to remember that SMB buyers often want your product to help them with that chore they need to do, but don’t know how (or want) to do. This gives you a huge opportunity to offer additional value–your time and expertise. 

You may offer the world’s most effective product, but the reality is when an SMB buyer selects your company and product, they are also selecting you. If you can demonstrate your support early and often, provide best practices, and create a strong partnership, you are more likely to be selected, even if your product isn’t as strong as the competitors’.

3. Make the conversion and adoption process as frictionless as possible.

SMBs have a lot in common with consumer buyers. On one hand, they often have less-formal buying processes, and can move much faster to make purchases than enterprise clients. On the other hand, they have very limited time, little margin for error, and are attracted to simplicity. If you can’t show them immediately what value you provide and an easy path to it, you will lose the sale.  

The SMB sales process must be frictionless from beginning to end. Make your contracts and pricing transparent, easy to understand, and easy to opt in and out of. You must also find ways to work with the tools and process the business has in place. In addition, it’s important to remove any educational and financial barriers to entry. Things like free trials and the ability to easily scale packages up and down will make it easy for SMB buyers to start simple and expand.

Don’t make customers jump through hoops to get to your product, and make it easy for them to see demos and provide a credit card to begin. Once they are in the product, help them get to that first “aha” moment quickly. This is where your team must continue to provide support, even after the trial. 

Since coming to ActiveCampaign, I’ve had the privilege of managing the entire sales funnel as well as the customer success team. I’ve had to focus on closing the deal, as well as those first critical 60 days post-sale. What I’ve learned is: Simplicity and support must be built-in from the get-go. That includes good content (help guides, videos, etc.) that continue to teach customers on a personal level without taking away time from either business (yours or theirs). 

4. Build advocacy by starting with trust.

Just because it’s frictionless, doesn’t mean it should be impersonal. There is an opportunity in that; if you can become a trusted partner early on you are most likely to have that customer’s loyalty, and therefore advocacy.

Always remember that small businesses are more connected to their spend and to the risk of the business. Many SMBs rely on personal investments or loans to finance their business, and failure is not an option. Understand this customer POV and build rapport with them over price.

Many small businesses, around 47 percent, are looking for guidance and support when it comes to their technology investments. And in absence of turning to Gartner and other analysts to learn about products, they are turning to peer reviews. As such, customer experience and sustaining good customer sentiment is important in maintaining your reputation with SMBs.

Ways you can do this are to include trust as part of your offering, we have done this with our customer commitment, and also have created a vast library of helpful and educational content that teaches marketers, CEOs and whoever is curious about our product, how to get the best results. We go beyond core product training to help our SMB users understand how concepts like “deliverability” contribute to their customer engagement strategy. It’s important that we aren’t just pushing a message to get a company to buy, we are truly providing guidance to them.


5. Rethink your approach to return on investment.

Finally, one of the best parts of selling to SMBs is that you get to be creative. While in the enterprise, you are most likely working with a functional lead or financial decision-maker who has set a budget, outlined a list of goals, and is executing to those goals. When you’re selling into SMB, your days are much more varied. 

And while enterprise buyers have a very narrow definition of ROI (and you spend half the sale convincing the team your ROI calculations makes sense) you can be creative about what your value proposition is when working with an SMB. Understand that lifestyle improvements can be part of the ROI calculation and things like risk, money, reward, emotional reward and life betterment factor into the equation. For example, saving an SMB owner time not only helps their business, but also gives them more time for family, hobbies, etc.

This reimagining of ROI goes both ways. When selling into the enterprise, it’s all about that one big deal. But when you’re selling to an SMB, you must embrace the idea that ‘shavings make a pile.’ You can’t scale into the massive SMB market with an enterprisey, big-deal first mindset. What the small business market lacks in depth, it more than makes up for in breadth and scale; just take a look at Google, which has over 3 million small businesses paying for its productivity tools. 

In Conclusion 

To capture a meaningful, sustainable share of the SMB market it is important to lead with the motivation of creating value for them, not just creating value for your company. Are you willing to build a product or service that is appropriate for them? Are you willing to do business on terms that are appropriate for them? Are you willing to continue to do this over time as your business grows.

If so, small businesses can be a powerful vehicle for growth, and a great opportunity for any business. 

Adam Johnson is the senior vice president of sales and customer success at ActiveCampaign, where he is scaling the sales and customer success organization to deliver growth and engage with customers. Prior to joining the ActiveCampaign team, Adam was an area vice president of SMB sales at Salesforce, where he led sales teams and developed a passion for helping small businesses use technology to drive results. Adam serves as an advisory board member to Urban Alliance and Sales Assembly, and is a mentor to early-stage tech companies through VentureScale. He won the 2019 Stevie Award for National Sales Executive of the Year.

  • Originally published July 1, 2020, updated September 21, 2021