Chapter 4

Collaborative Learning in Sales

It takes a village to train a sales rep.

In the winter of 2014, Derek Rahn joined sales-generation startup, LeadGenius, as its senior account executive. Rahn’s onboarding was typical of a small, under resourced startup. Over the course of 6 weeks, Rahn sat in on a handful of ad hoc, ride-along sales calls—and then he was set loose on his territory.

As a seasoned sales vet—Rahn had already worked in half a dozen high-performance sales teams—he found his feet quickly and started landing large, enterprise deals. But his colleagues weren’t so successful. Many were relying solely on the lightweight ride-along training and were focussing solely on easy, low-hanging fruit in the SMB market. In fact, Rahn estimates that 90% of LeadGenius’ revenue came from easy startup wins—and that wasn’t sustainable. Startup revenue was volatile and could never support LeadGenius through its next phase of growth.

Over the next few years, Rahn harnessed LeadGenius’ internal expertise, overhauled its sales training, and shifted the sales org’s focus from unprofitable SMB contracts to lucrative enterprise deals.

Drunks Selling Beer to Drunks

Rahn joined LeadGenius when the company was just three-years-old. Its sales team was small, processes still largely undocumented, and training budget virtually non-existant. But this is pretty typical for an early-stage startup. “[Startups] don't have a training budget,” Rahn told 360Learning. “They don't have a trainer. Some don’t even have an HR professional.”

With few resources to call upon, the company’s sales-management team implemented what little training they could. “All we did was ride-alongs in calls,” Rahn said. “We sat on the phone, listened to conversations, and learned about the industry that way.” After the briefest of sales training programs, LeadGenius’ sales reps gravitated to other startups. Startups felt familiar and they shared the same challenges, which made it easier for the sales reps to get their foot in the door and land the sale.

At this time, more than 90% of LeadGenius’ revenue came from SMBs, although Rahn says this was almost exclusively from startups. And that’s a problem. Startups were notoriously flaky. They regularly ran out of cash, either through financial mismanagement or simply by failing to secure a new round of funding. “They would email and say, ‘Sorry, we can’t pay for your services anymore,’” recalled Rahn. This caused huge revenue fluctuations as customers regularly disappeared overnight.

The turning point came in early-2015 when one of LeadGenius’ VCs recommended they stopped selling to startups. “It's like a bunch of drunks selling beer at a bar to each other,” the VC explained, according to Rahn. “Eventually, it's going to be time to go home and everyone's going to be broke and drunk.” The message bounced around the sales team before making its way to senior executives, where it landed with a thud. Soon after, rumours started drifting back down that LeadGenius’ management had taken the advice onboard and was shifting its focus away from easy startup sales to focus on bigger deals.

Swimming Upmarket

Before joining LeadGenius, Rahn cut his teeth in enterprise sales. At Endurance Group International, he sold web services to blue-chip clients. At Envoy Data Corporation, he sold data security services to multinationals. Getting inside large-cap companies and pitching decision-makers was his bread and butter—and he continued that work at LeadGenius.

During his first year, Rahn individually sold several huge enterprise clients, including Box, Square, and Google. “That gave LeadGenius the confidence to say, ‘Okay, we're going to try and get away from the volatile type of revenue we’re getting from startups,’” said Rahn. With Rahn already walking the walk, LeadGenius’ head of sales asked him to show the old sales reps how to mimic his work and close bigger deals. But that was easier said than done.

LeadGenius wasn’t selling a basic app or a standardized piece of software. “We sell a service,” Rahn explained. “And we consult on a whole slew of different problems.” With that level of complexity, sales reps couldn’t just read through a script, demonstrate some features, and know that they’ll close the sale. When LeadGenius’ reps approached larger organizations, they were talking to people who were in the trenches day-to-day. If a sales rep didn’t have a background in data, it was almost impossible to win over enough stakeholders to push the sale forward.

Consider data security, which is a large part of any data sales process. In Europe, the EU introduced a set of strict new data management rules named General Data Protection Regulation (GDPR). If a LeadGenius rep started talking to a European company, it was a given that the prospect would ask a few questions about GDPR compliance. “If the rep couldn’t give the right answer, that’s an immediate disqualifier,” Rahn explains. Enterprise organizations receive dozens of pitches a day and need only the slightest reason to discard a provider.

Rahn, who had been promoted to Head of Enterprise Sales while he was designing the new training program, knew his sales reps needed to understand the industry—but he wasn’t sure how to collect all of that information and effectively communicate it to them. Little did he know, that fortune was about to smile upon him.

In July, 2017, LeadGenius appointed a new CEO named Mark Godley. During Godley’s first week, Rahn stumbled on the new CEO chatting with a huddle of employees. He was discussing the data industry, talking through his background and explaining his take on everything from regulation to open opportunities. As Rahn stood on the sidelines listening, Godley explained the difference between firmographic and technographic data, discussed the nuances of GDPR, and broke down the messy, interconnected data industry. Rahn was blown away both by the depth of Godley’s knowledge and the quality of his communication. “I thought, ‘This needs to be part of our training,’” Rahn said, recalling his reaction. “Almost all the content is already there because he knew the stuff inside out.”

After the meeting, Rahn pulled Godley aside and asked if he could repeat exactly what he just said in regular training sessions to new sales reps. Godley, who liked nothing more than discussing data, agreed instantly. And just like that, Rahn had the first module of his new training program.

Illustration of the Collaboration between learners at LeadGenius

Calling on Experts

With a good training foundation in place, Rahn went back to his reps’ latest calls, expecting to see a significant improvement. But instead of a mountain of closed deals, he found a bunch of opportunities lingering in the sales pipeline. After a bit of digging, he discovered the problem: personas.

When Rahn’s team was selling to startups, they were typically dealing with a founder, who knew a little bit about a lot of subjects. With startups, as long as LeadGenius’ sales reps could talk confidently about the data industry, there was a good chance they could close the deal. But the company shifted its focus onto enterprise businesses, Rahn realized they were dealing with an entirely new breed of specialized employee. Now, they were selling to senior marketing and operations executives, who wanted to talk about the nitty gritty of data in their specific niche. “We were missing a lot of context,” Rahn said. “How do these different people interact with data? Why is it important to them or why should it be important to them?”

Again, Rahn knew this was a great opportunity for a new training module. And after the success of his CEO-led industry training, Rahn knew exactly where to go for specialist persona training.

He corralled the company’s operations director, Adam Louie, and then Director of Marketing, Greta Oberschmidt, and gave them a fairly flexible brief—teach my reps everything they need to sell LeadGenius to you. Then he left them to design their training curriculum on their own. Asked why he didn’t take on these modules himself, Rahn laughs. “If I tried to do the ops training, the reps would come out more confused because I'm not an ops person.”

After a few weeks, Louie presented his ops training course. It was the equivalent of an Operations 101-level college course, covering all the basics and equipping sales reps with everything they’d need to deal with operations professionals directly. “[Ops training] is important because ops is more important now more than ever,” Rahn says. “Ten years ago, sales ops professionals didn't even exist.”

On top of basic operations knowledge, Louie added a plethora of in-depth persona insights. He explained how ops professions thought about business decisions, why being data-driven was important to them, and how LeadGenius’ data could help them. “The module gave them enough information to be dangerous,” Rahn said. “It allowed our team to talk about the world that ops professionals live in.”

A quote from Derek Rahn reading "They really have to understand what a data is to a marketer, why they need it, and what success looks like to them."

Soon after Louie confirmed his training module, Oberschmidt presented her course. Oberschmidt’s course was similar to Louie’s, a crash course on marketing terminology, definition, and processes. “The course makes sure that you can actually like talk that talk coming in,” Rahn explained, “and that you can actually understand the meaning behind it.” On top of that, Oberschmidt dug into the specific challenges, needs, and wants of marketing executives. “They really have to understand what a data is to a marketer, why they need it, and what success looks like to them,” Rahn said.

Rahn is careful to point out that these training modules—marketing and operations—only make sense for LeadGenius because of who they’re selling to. If they sold to finance execs, he would have asked LeadGenius’ Chief Financial Officer to create a training program based on finance buyer personas. If they sold to software engineers, he would have turned to LeadGenius’ Chief Technology Officer. For persona sales training to be effective, it’s got to be tailored to the type of buyer your reps are selling to.

With the foundations laid and specific persona training designed, it was time to put everything into practice in a final module, one Rahn had saved just for himself.

Putting Everything into Practice

Rahn compares early sales training to a baseball-training drill called “pepper.” In pepper, batters practice hitting grounders and line drives to a group of fielders, outside of a real game situation. Kids usually hate the drill as they can’t see how the repetitiveness will help them. But that all changes when they step onto the diamond for a real game. “They get into a real game and they’re like, ‘Oh, these are the same throws we’ve made in pepper a hundred times,’” he says. Sales training works in the same way. Managers train basic skills and then reps put them together in a game situation.

In the foundation and persona modules, Rahn’s reps learned all the skills they required to sell to enterprise clients. But before Rahn sets his reps loose, he added in one last module. “The last module is actual use case training,” Rahn says. “That has to do with why a company actually uses us.”

In the last module, Rahn presents real leads and challenges his reps to use their skills and analyze the opportunity. “They learn to say, ‘Hey, you’re a marketing ops person at a mid-market FinTech company,’” says Rahn. With that analysis comes an ability to identify their needs, challenges, and objectives. But that’s just half of the module.

Once reps have identified who they’re talking to and what they need, Rahn drills down on narrative. After a sales rep has proved that they understand a prospect, they still need to demonstrate how LeadGenius can help. “It's really about telling the LeadGenius story and telling the story of differentiation,” Rahn says.

Illustration of Collaborative Learning program at LeadGenius

Your Colleagues are a Resource

Too often, sales training is treated as only a sales issue. Sales leaders will often try to design and present a full curriculum themselves—and that’s a recipe for disaster. Niche subjects demand subject matter experts. “When you try to do something, in which you don't have subject matter expertise, you lose some of the meaning of what you're translating,” Rahn says. When you present a confusing or incomplete message, you inevitably impact your final result, which, in this case, is the competency of your sales reps.

Since introducing collaborative learning to the sales team at LeadGenius, Rahn has improved the teamwide win rate from 10% to 22%. But it’s not just the number of clients Rahn’s team is closing, it’s the size of them, too. When he started at LeadGenius, just 10% of its customers were enterprise. Now, that figure is 90%. Better yet, Rahn slashed LeadGenius’ sales ramp from nine months to just five.

The next time you are designing a sales training program, don’t try and shoulder the burden yourself. Reach outside your sales org and ask for help from experts in management, marketing, and operations. With their help, you can design a comprehensive sales training program that helps reps understand your entire industry, rather than just a sales script.