As the VP of HubSpot’s corporate sales division, I’m not just looking for great sales reps -- I’m looking for great reps who can sell to midmarket and large businesses. And while there are certainly similarities between the two categories, there are also some notable differences.

First, the similarities. Regardless of what size of company or industry they’re selling to, excellent sales reps prospect well, and maintain high levels of activity. They ask smart and incisive questions and listen carefully to qualify thoroughly. They’re able to build trust, demonstrate exceptional product knowledge, and they can close. These are skills that are transferrable no matter what type of customers you are tasked with closing.

But there are a few additional competencies that reps selling into midmarket or large businesses need to possess. The top four in my view are a talent for team selling, an ability to navigate complex organizations, a propensity for reference selling, and a knack for leveraging all revenue generation channels.

Let’s dig into each.

1) Team Selling

In a midmarket or enterprise sale, the number of stakeholders on the buyer side is multiplied, and so is the number of people involved on the seller’s end. Whereas a small business deal often takes place between one business owner and one sales rep, a large business might bring five to seven stakeholders to the deal, and the salesperson should loop in a similar number of people on their side.

I think of large business reps as deal quarterbacks. Instead of doing all the legwork themselves, they are able to effectively organize their colleagues so each person can have an impact in the right place at the right time. Much of this is a matter of matching up the buyer’s stakeholders with similar internal resources. For instance, legal departments at complex organizations usually review contracts before they are signed. A savvy rep will set up the buyer’s legal team with a lawyer at the seller’s organization, so the two can work through any issues quickly. This not only expedites the deal, it also boosts the selling organization’s credibility.

2) Ability to Navigate Complex Organizations

It’s extremely difficult for an outsider to understand organizational dynamics. That’s why I recommend that reps selling into midmarket and large businesses recruit either a coach or champion within the buyer’s company. A coach is a person who can explain the lay of the land. A champion can also do this, but additionally wields the power to move the deal along on the seller’s behalf. For this reason, a champion is more valuable than a coach, although both are helpful.

How can you identify a champion? If your company uses an inbound marketing model, the champions often reveal themselves by downloading an offer or clicking on a pricing page. If you don’t have this type of information at your disposal, get on LinkedIn and look for roles and people that you think would have the challenge you propose to solve. However, keep in mind that a person’s title doesn’t always accurately indicate the amount of sway they hold. Be willing to do some digging and meet several people before you strike on your champion. 

Determining if someone is a champion or a coach is easily done with a simple test. After your first call, ask if your contact would be willing to gather their colleagues for a follow up meeting. If they’re able to corral the necessary people and make the introductions successfully, they’re a champion. If not, they’re probably a coach. 

3) Reference Selling

Small businesses are generally more willing to take a risk on a new product or service. Midmarket to large organizations, on the other hand, want proof. And not just your assurances -- large business leaders want to see results from a company that closely resembles theirs.

With this in mind, reps selling into mid-sized or large organizations need to be able to use references to their best advantage. Whenever they go into an engagement with a prospect, they should have at least one or two case studies at the ready -- whether that data is inserted into a presentation, or recited from memory. The examples they use should cover the results of a similarly sized company, and ideally within the same industry. 

4) Using All Revenue Generating Channels

Sales reps who sell into mom and pop shops don’t have much opportunity for upselling outside of offering a different product or service line. After all, there aren’t any other business lines or functions within the shop -- it’s just mom and pop, and they already bought.

But the opportunity for upselling and cross-selling is much greater in a midmarket or large business that does contain multiple divisions. Since new business doesn’t close as quickly in the enterprise space as it does in the small business market, reps who work large accounts need to exploit their relationships with current customers to make their number. Is there another function within the company that the buyer could refer you to? Perhaps an opportunity to work with channel partners? An aptitude for both hunting and farming is a must for an enterprise rep. 

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Originally published Nov 10, 2014 11:00:00 AM, updated July 28 2017

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