Up your cross-sell game, with Zendesk’s Norman Gennaro

We see a common mentality around the cross-sell motion that it is the lowest hanging fruit possible in sales. Norman Gennaro, Zendesk’s President of Global Sales & Field Operations, says nope.

“I think a lot of people underestimate how hard cross-selling can be,” he says.

He’s seen this manifest throughout his career, including 16 years running sales consulting groups at Oracle, six years with AWS and another six (and counting) at Zendesk. The growth Norman has overseen at each organization relied on positioning a large number of products—and doing so sustainably, for the benefit of the customers.

We spoke with Norman about capitalizing on the cross sell, and we walked away with these five key insights into cultivating relationships, emphasizing organizational fit in the sales cycle, balancing the cross sell with net-new accounts, when to incorporate product specialists on the sales team and leveraging customer success into more strategic targeting practices.


Identify your champions and cultivate those relationships

To better identify cross-selling opportunities, Norman expands the typical, fairly narrow definition of cross selling. It’s not just about signing up an existing customer for related or supplemental products. For him, it’s about building (and leveraging) substantive relationships.

“A cross sell can be thought of in a number of ways,” he says, “beyond selling into your existing customer.”

  1. Think about cross selling not as selling into an existing customer, but to your existing champion within the account. This redefines your sense of “customer” from a company that cuts the checks, to an individual (or a group) that understands the applicable value of your product and uses it to make their jobs better.
  2. Think of cross selling into another division or part of the company. “Your champion inside of your account can help you open those doors and have those conversations,” Norman says. “You really want those champions to help you get to the right person, to make sure you’re talking to the teams that care about what you’re positioning and see the value in it.
  3. Think of cross selling into entirely new accounts. Sure, this might not technically go down as cross selling. But if you build those relationships with your champions, you’re not starting from scratch when they switch roles. “People move around inside of companies, but also outside of them,” Norman says. “If they had a great experience with you at one place, they will typically bring you into their other companies. They will be references for you for life.”

Reframing cross selling as expanding on substantive relationships with your champions shifts the focus from closing sales to developing long-term connections.

 “Most top-quality salespeople won’t burn a relationship just to push a product in,” Norman says. “They really want to make sure that the product’s value is key to the customer.”


Build a sales team that prioritizes organizational fit

Norman builds heavily on top of this foundation when approaching the cross-selling motion. Looking out for your relationships and working from a place of relevance, not quotas, establishes trust.

This way, cross selling becomes more about finding the best fit for a product, by talking with the right people—both within existing accounts and in lookalike prospects.

“How do we actually think about our existing customers?” Norman asks. “Where do they match up with a new product we’re bringing to market? Who should we talk to? Who are the lookalikes?”

The tailored perspective that results from asking such questions can shape the way you build your sales team. How to build the right motivations on the team, within the right infrastructure, to conduct an effective cross-sell motion ultimately depends on what you’re trying to cross sell.

Because, in short, just treating those champion relationships like standard sales prospects is not going to do you or your product justice. You want to make certain that the product your sales team is talking about is something customers can actually see benefit to using. As Norman stresses, we all know that shelfware is a killer.

“There are a lot of different complexities to building a sales team this way,” he says. “Are you selling an add-on that naturally connects into what your customers are using? Or is it a separate product that is solving a different use case issue? Does it require development expertise? Does it require a different type of selling motion in and of itself? These are important aspects to consider as you’re building out your sales team.”

Yes, thinking of the cross-selling motion with such nuance may seem to complicate what many sales leaders see as a simple upselling function. But in the current environment, customers are seriously assessing value—and trimming the fat. Staying relevant with customers is key to staying with them at all.

“Companies are consolidating the number of vendors that they’re dealing with, trying to become more optimized,” Norman says. “So a cross-selling motion where you can really describe what your products do and get them leveraged across an organization is an important piece of the selling motion today.”


Constantly balance cross-selling with net-new

We often observe sales teams struggling to balance cross-selling efforts with going after net new accounts. Not only is net new a sexy stat—you need to bring in fresh customers in order to have existing customers that can expand. 

“We are always biased towards new,” Norman says. “But the reality is that the expansion/cross-sell motion is easier. You will hopefully see those new customers start adopting products over time.”

So what is the right balance between cross selling and net-new? The short answer: it depends, and it depends on more than your own company.

Norman reflects on how the cross-sell expectations differ between his experiences at Oracle, AWS, and Zendesk. Even within one organization, the balance changes over time and often in response to the current economic environment.

“Right now, we are hyper-focused on retaining and growing our customers,” he says. “We’re not taking our eye off the ball in terms of new, and I expect [next year] we will significantly ramp up what we really want to do around new market share. But you have to have a little bit of reality based on where the economy is at a given point in time.”

Today, that means holding onto customers and getting them to do more with your products. At some point, the season will be ripe for net-new. The balancing act is always in flux—so when times call for it, lean extra into the cross-selling motion, and know that net-new will return.


Incorporate product specialists as needed 

Yes, cross selling is a sales motion. But while part of that cross-sell/net-new balance, it’s an entirely different game than signing new accounts. Norman identifies specialization as a fundamental requirement for most cross-selling organizations.

“We are always looking at the complexity of our products and what is required to make them successful for a customer,” Norman says, “especially the farther the products get away from the core. Typically, sales consultants with those specialties allow you to get the best bang for your buck.

Now, to be clear, his own bias is a preference for an entire sales team selling all of an organization’s products. That enables the most scale—but it often doesn’t work. Generalist salespeople, no matter how good they are at sales, likely lack the expertise to get the customer where they want to be.

“Having a dedicated salesperson who can run that sales cycle to the end is important for the scale and speed you want for the rest of your sales organization,” Norman says.

Incorporating specialists into the cycle also ups the expertise across the organization. Over time, as the sales team interacts with the specialists and observes the products in place, they will increasingly understand the nuances of specialty products. The need for additional specialist capacity likely decreases as specialized knowledge and capabilities become integrated into the team.

That expertise allows you to get the adoption, allows you to target better, allows you to find the actual lookalike accounts so that you know where you should be winning and where the edge cases are,” Norman says. “In many cases, those edge cases can still be owned by the specialist team, even though the core team will take on some of the responsibility for positioning the product.”


Final thoughts: Build your targeting strategy on top of customer successes

The necessary focus on how to cross sell leaves one big final component to consider, and that’s why to sell: because you’re helping customers succeed.

If you’re truly building relationships, selling to fit, and outfitting customers with essential specialization in the sales cycle, you’re going to end up with some powerful references—and there is no better way to demonstrate your value to one customer than to show them the outcomes from another customer.

Those resulting customer stories are also one of the greatest cross-selling assets available to your sales team’s efforts. Broken down and analyzed, customer stories can boost a sales team’s internal performance, understanding of the products and targeting strategies.

“Early wins are critical to convert into references, to leverage as part of your marketing campaigns,” Norman says. “But also—a key way to operate at scale is to take your wins and make sure the entire sales team understands where you’ve been successful, so that they can better target. That’s one of the ways our sales teams understand who they need to go to next and how to make sure they’re covering the market well.