Building an enterprise sales team from the ground up

How did Custom Ink transition into enterprise sales? In many ways, CRO Ryan Massimo was hired to facilitate its enterprise transition—and to do so, he focused on four pillars:

• Upgrading the company’s tech stack, specifically its Salesforce and ZoomInfo capabilities to focus on outbound and lead generation. “We had different sales teams that were on different platforms, so we had to consolidate that all to something that’s consistent.” Massimo told Revenue Brew.
• Creating better training materials, which Massimo told us came down to being diligent about collecting employee feedback.
• Restructuring teams to emphasize outbound (instead of the inbound and prior relationships). Employees were moved to new teams and given new responsibilities according to their skills.
• Revamping the sales curriculum, changing incentives and compensation plans.

Trust the process

Amanda Hanlon, VP of inbound sales, has spent 16 years at Custom Ink. When the sales transition happened, she said the change in culture was effective but ultimately rooted in the mission of the company.

“We’ve never wanted to be sales-y,” Hanlon said. “But I think what we realized is we’re not sales-y. We’re guiding people. The way in which we’re approaching customers is: We have a solution to give you, and we actually know problems you may not even be aware of.”

Hanlon says her team has created an “elevated guiding approach,” starting with reevaluating team staffing and assignments.

“We just needed to pivot and make sure that we had folks in the right place, so whether you’re customer success or outreach field sales or enterprise sales, making sure that that role matches your skill set,” Hanlon said.

Hanlon explained that, at first, the change was disorienting for staff. However, she says the new teams “understand the vision.”

Expert insight: enterprise transitions

According to Jamie Cleghorn, senior partner at Bain, companies often decide to make enterprise transitions because their customers are asking for it. Cleghorn explained that this is a preferred way to head to enterprise because there is proof of concept.

“A product-led growth [PLG] company, oftentimes the reason they’re going to make the migration is because they’re seeing: ‘We actually have a bunch of PLG instances at this [company],’ and the companies come to us and say, ‘hey, can we get a different arrangement on pricing?’”

Cleghorn also said that product-led companies are talented at building an effective path to purchase, in part, because they already have the commercial infrastructure.

“Most successful PLG companies or sales-led, at the lower level, it’s a very engineered happy path of purchase. It’s a frictionless buy. You can do it all online, click down the happy path.”