Moving Upstream

How to Know If You’re Ready for the Enterprise Market


If you want to start selling to enterprise customers — the coveted large accounts with bigger revenues — it’s important to first consider exactly why you want to do this, and whether you should do it. If the reason is because you’re not doing well in SMB arena, then it’s time to reconsider, because struggling in a smaller market segment is not a good harbinger for success in a larger one. However, if your sales look good and you feel that a move upstream is the next natural expansion for your company, then you might be ready to explore a new market.

At SalesHacker’s 2018 Revenue Summit held in San Francisco, a group of sales executives took on the topic of moving upstream to enterprise — here are some of they key takeaways.

Taking on the Challenge

Part of the attraction of moving upstream is the lure of pursuing new, higher-revenue customers. While this can happen organically with one or two interested companies, intentionally targeting large companies involves a lot of planning and requires company-wide buy-in.

According to Jameson Yung, VP of Sales at, if you’re starting to attract enterprise customers and you’re thinking of taking on more, it’s important to first take a look at the customers who are making you want to go upmarket. Do they represent the rest of the market, or are they unique in some way? If they're fairly representative of the larger market, this can help clue you in on what to expect from the outset.


Before making the transition, it’s crucial to do your homework and align your product — as well as your resources — to your new customer base.

However, according to Michael Coscetta, global sales VP for Square, it’s important to remember that selling an enterprise product is a very different experience than selling a consumer-driven product. The customer often expects reps to have expertise in their industry and its unique needs — and they expect a more high-touch approach throughout the relationship.

“It’s [about] attracting the higher-end customer, it’s maintaining the higher-end customer, and then growing revenues with those customers over time,” he said.

According to Coscetta, the needs are far greater for enterprise customers. Plus, there are extra considerations over legal, data and security requirements — and it’s often on the sales rep to get creative and work within their company to figure out how to accommodate the customer.

“It’s about putting all that on paper, and building that strategy matrix of all the different things that need to be lined up to do it properly — and then of course supporting it with dollars, with activity, with knowledge, with know-how,” Coscetta said. “As you move up in size, that customer tends to expect a higher level of understanding and expertise for you to be able to sell to them.”

In the end, if you want to win and maintain enterprise customers, it’s essential to align your company’s supporting resources to meet these demands and be compliant.


Another huge difference between enterprise customers and mid-market customers is in the time frame. For a variety of reasons (more stakeholders involved, more complex internal processes, increased budgetary considerations), enterprise deals typically take longer. This longer time frame can be a benefit, Coscetta said, if you know how to leverage it to meet your customers' expectations.

“Start to set milestones,” he advised. These points of accomplishment can keep the customer motivated and excited and will help show that the company is on track.

In the end, it's important to make an informed, educated and deliberate decision as to whether a move upstream to enterprise is right for you. The important thing is to be prepared and be able to sell the idea that your company can swim right along with the big fish in the larger pond.

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