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ConnectWise Sales Director: Look For Salespeople With Technical Expertise, Creativity And A Strong Work Ethic

Solution providers also should find a way to assess whether the individuals are solutions salespeople or if they're just selling point products, says Kyle Jackson, ConnectWise's major account sales director, in a session at XChange 2017.

Solution providers would be well-served by hiring salespeople with strong references and giving them 10 months to get fully up to speed, said a ConnectWise sales leader.

For solution providers, the process of hiring their first salesperson should begin with a reference from someone who has a pre-existing relationship with the company and can directly attest to the individual's technical expertise, character and work ethic, said Kyle Jackson, ConnectWise's major account sales director, in a session at XChange 2017.

"If someone you know can actually attest [to the fact that] they're good, you'd be surprised at how far that can go in your ability to trust them," Jackson said.

[RELATED: ConnectWise To Add AWS, Cisco To CloudConsole, Double Number of Users By End of Year]

Most of ConnectWise's hiring is does on a relationship basis, meaning the Tampa, Fla.-based IT service management vendor typically only hires people who already know someone in the company and can therefore be personally vouched for.

The most important characteristics Jackson said he's looking for in a prospective salesperson are ethics and honesty. This can be tough given the stigma around used car salespeople, Jackson said, which can sometimes dete people from seeking a career in sales.

"They're representing you on the front line," Jackson said. "And when it goes wrong, they may be gone and go get another job, but you're taking a reputation hit."

After that, Jackson said he looks for salespeople with creativity, meaning that they're capable of thinking on their feet and having a conversation even when they don't necessarily know all the answers. Creatively having a way to move to move the conversation forward even if the salesperson doesn't know all the information is vital, Jackson said.

"Not having the answer and saying 'no' is not the right answer," Jackson said.

Part of the onus falls on the employer as well to help salespeople understand common questions as well as how they should respond, Jackson said. A business owner might be used to giving clients a "hard yes" on the spot to unusual or unorthodox requests, Jackson said.

While most owners don't typically allow their salespeople to sign off on unique requests, Jackson said they should understand what to do if they find themselves in that scenario, even if it's something as simple as calling the business owner for verbal permission.

Beyond that, Jackson said he wants salespeople that are hungry and aspire to blow out their quota or targets.

When interviewing a potential salesperson, Jackson recommended asking questions that look at their ability to manage daily activities and their attitude and demeanor around making phone calls.


During the conversation, Jackson said employers need to find a way to assess whether the individuals are solutions salespeople or if they're just selling point products. Any salespeople who say they rely on using a discount to close the deal should raise major red flags and be avoided "like the plague," Jackson said.

A solution provider's first or only salesperson shouldn't be a lone wolf, Jackson said, meaning they should be working from an office environment rather than from home. Solution providers should also ensure their new sales hires are coachable so that they can be trained and taught necessary technical skills, Jackson said.

Although it might take new salespeople 10 months to fully ramp up, Jackson said employers aren't doing salespeople any favors by keeping them on board if they're still not producing after that time. In that situation, Jackson recommended that solution providers either terminate their employment or find them another spot in the organization that isn't so quota-driven.

Up until that 10-month juncture, Jackson encouraged solution providers to look at how effectively their new salespeople are creating opportunity by either growing the prospect pipeline or making phone calls and visits to potential clients.

"They might not be closing business, but are they meeting other metrics that will help with closing business?" Jackson said. "If they're not even trying to hit their numbers, then let them go. Don't wait the entire period."

Jackson's presentation provided NorthEast Computer Services with great insight into the mind of a salesperson, specifically as it relates to what they're looking for and what processes need to be in place, according to President and CEO Eric LaFleur.

The Haverhill, Mass.-based company still needs to get well-established goals and metrics in place before hiring its first salesperson, LaFleur said. NorthEast Computer Services also needs to ensure that it is growing its sales and technical capabilities together, according to LaFleur.

"You've got to grow smart," LaFleur said.

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