Chapter 1

Building a Sales Enablement Team

Why sales enablement should be your second sales hire.

In July 2011, Michelle Kanan accepted her first sales enablement role at a small kitchen appliance company called iTouchless Housewares. Enablement as an industry was still in its infancy and Kanan’s bosses didn’t even have a solid name for her role. She was tacked onto the larger sales org and tasked with improving workflows, performing sales analysis, and designing sales strategies.

Kanan was only at iTouchless for one year but during her time there, she increased sales by 30% across the board, hammering home just how effective sales enablement could be.

More than a decade later, Kanan still works in sales enablement, which has evolved from an unloved and misunderstood concept into a highly respected occupation. As an industry, it owes much of that new respect to enablement specialists like Kanan, who have spent their careers lobbying for a seat at the table.

Illustration of Michelle Kanan deploying sales enablement content

What is Sales Enablement?

When asked what sales enablement actually is, Kanan has a simple answer: “It’s the work sales managers do when they're really good at their jobs and they really care.” In other words, sales enablement involves designing onboarding programs and ongoing training plans; it’s documenting institutional knowledge and maintaining that knowledge library; it’s coaching sales reps, analyzing performance, and creating templated sales collateral. But it hasn’t always been this way.

Ten years ago, sales enablement barely existed. “It started out as enablement for sales assistants,” explains Kanan. Few companies with inside sales teams ever thought to invest in support for their sales reps. Instead, they were content to ride on the back of their natural sales acumen.

But over the years, as the inside sales industry matured, sales leaders started to wise up. Innovative sales teams realized that enablement deserves investment—and they’re pushing ahead. In high-performing teams, sales enablement professionals sit alongside sales managers and the two roles help each other achieve common goals.

After getting the taste or enablement at iTouchless, Kanan went in search of bigger projects and, in April 2014, joined the Discovery Channel as an advertising solutions coordinator—their term for sales enablement. There, she learned how a large organization deployed enablement to improve performance across its entire sales org. “The focus was helping reps who were working on huge TV buys for advertising,” she says. “I really learned the ropes there.” Kanan learned how to build onboarding programs, design training materials, and educate a large workforce. She learned how just one person’s work could affect change across a whole workforce, driving tangible growth in a business.

At the end of her two year tenure, Kanan was equipped with all the skills and experience she needed to build a team from scratch—so that’s exactly what she did.

Your Second Sales Hire

After leaving the Discovery Channel, Kanan joined a succession of startups—a video distribution platform called Virool, an analytics service called Periscope, and a recruiting tool called Lever. At these companies, she experienced organizations with varying levels of enablement maturity. Some had prioritized enablement from day one, others had put it on the backburner until they couldn’t ignore it anymore. And that taught her invaluable lessons about when organizations should make their first enablement hire.

At companies that ignored enablement, Kanan discovered that the enablement work was still always done. But since the sales org didn’t have a dedicated sales enablement hire, the work was picked up by high-performing reps and managers—and that was a problem. When you stack a sales-enablement workload on top of an already full schedule, it’s only a matter of time until something breaks. “If you don't hire somebody for enablement, it always causes extreme burnout of your A players,” Kanan explains.

Burnout isn’t the only problem, either. When sales leaders take on extra enablement work—either because they choose or are told to—it’s almost never their primary focus. “It’s always reactionary,” Kanan says. “Sales enablement work is squeezed into slivers of free bandwidth and people get to it whenever they have time.” Because work was spread between a dozen different people, the overall body of work became fractured and disjointed.

Think of enablement as a huge filing system, suggests Kanan. When it’s managed by a dozen people, all the pieces of paper are stored in a dozen different locations. Worse, since there’s no one person directing the strategy, every single piece of work will have a slightly different focus.

For a new sales enablement professional in such an environment, they could easily spend their first few months sorting through the information maelstrom. Indeed, Kanan has done just that. “There's so much debt that has to be repaid,” she says. “You're picking up each piece of paper, trying to figure out what it is. Is anybody still using it? Is it still relevant? Where do I put it? How do I organize it?” All the time someone spends clearing up is time they aren’t spending building something new.

But at other companies, Kanan discovered how effective an early sales enablement hire could be—even for single-person sales teams. Sales enablement can effectively augment any sales team and whether that team has one or one-hundred employees doesn’t matter. “Hire an enablement professional as soon as you have a sales team,” Kanan recommends.

A quote from Michelle Kanan reading "You need somebody there to make sure that all the tribal knowledge gets documented"

Even in single-person teams, there is a glut of sales enablement work to do. While some of the work is beneficial immediately—for example, sales training and coaching—many tasks will pay dividends later down the line. “You need somebody there to make sure that all the tribal knowledge gets documented,” Kanan said. Without that, sales knowledge lives within individual people. If those custodians of knowledge accept a new job elsewhere or retire, that vital knowledge goes with them.

The Perfect Candidate

With such a varied and important—and still largely misunderstood—remit, finding the right person is a challenge. Before starting the hiring process, Kanan says organizations must decide what level their enablement hire will sit at.

In the winter of 2018, Kanan joined revenue intelligence startup, Gong, as its director of sales enablement, although she says her remit was wider, covering all revenue enablement, from pre-sale all the way through to post-sale. As Gong’s first enablement hire, Kanan was tasked with setting the overall strategic vision and building out its entire team from scratch. Her first task was to take stock of her stakeholders and work out what each of them expected from her—but that was easier said than done. Kanan supports the SDR team, AE team, CS team, and growth team. Each of the four segments had around five managers. So right from her first day in the office, Kanan had 20 different people all expecting different things from her.

“I'm trying to work directly with managers and directors to build out programs for their specific business,” she says. “And that can become unwieldy as context shifting becomes hectic.”

To deal with competing demands, Kanan focussed on the most “blanketed” initiatives and projects. By doing so, she could help multiple different segments and maximize the output from her limited time.

For organizations, such as Gong, that are hiring sales enablement leaders, Kanan recommends prioritizing experience and versatility. “If you're looking for a director or a manager of enablement, you need somebody who can handle 50 million priorities at once,” she says. “They need high output, attention to detail, and their focus must be on experience.”

But when an organization already has someone heading up sales enablement, the hiring calculus changes.

With a leader in place, it’s about identifying skill deficits and filling them with fresh hires. At Gong, Kanan split her enablement team into four go-to-market strategies—growth, SDR, AE, and CS—and created a dedicated sales enablement role to manage each. When hiring, she reviewed her skill set, highlighted her skills deficits, and brought on experienced people to fill the gaps. “I’ve never worked in customer success so I hired [someone with that experience] and taught them enablement skills,” Kanan said. “I hire for the skills that I don't have.”

In the future Kanan plans to subdivide her team even further, hiring people to manage, for example, enterprise sales within the AE team or SMB sales within customer success. “The motions are so different that you need an enablement person to tackle each one,” she says.

Create the Single Source of Truth for Knowledge

Before businesses bring on a sales enablement professional, it’s very common for their sales knowledge to feel fragmented and fractured. Perhaps your vice president of sales controls your overarching sales strategy, your sales operations manager understands your technology stack, and your sales manager handles your actual selling methodology.

With information siloed in a dozen different places, sales reps will struggle to work at their best. Say, for example, an account executive needs a case study to send to a prospect. With information scattered throughout their sales org, they have to spend a significant amount of time tracking it down. And when accessing information is difficult, reps will default to making do without it.

But sales enablement can counteract that by creating the single source of truth for knowledge in an organization.

That process starts with knowledge management, which is simply the process of capturing, distributing, and using the knowledge of an organization. In sales, that means collecting content, such as collateral and market research, data, such as plans and call recordings, and coaching, such as access to subject matter experts and sales leaders. With an organization’s knowledge collected into one place, sales professionals can quickly access any information they need to augment their own sales performance.

But there’s a problem. Knowledge management is a huge task. Capturing and coordinating the communal knowledge of even a small organization is a huge undertaking. For most people, it’s just too large a task to even begin. But for enablement professionals, it’s the perfect sort of project as they’re already working with the information. “[Sales enablement professionals] should manage all of the knowledge and be its keeper,” Kanan says. “That way they can keep a pulse on what's working and not working for SDRs, both in the pre-sale and post-sale.”

Although sales enablement should own knowledge management, it’s important they don’t shoulder the burden alone, says Kanan. In her first few months at Gong, she created structures to allow employees from marketing, product, HR, and sales to submit content, knowledge, and ideas they had developed and acquired over the years.

While knowledge management is a large task, there are some great products and tools available to streamline the process. But Kanan is quick to warn wouldbe knowledge guardians away from basic options. “Google Drive and Wikis are fine in terms of a storage location,” says Kanan, “but what they really fail to capture is the tribal knowledge.” To capture all of a company’s knowledge, including the easily missable tribal nuggets—a video, a comment, an article, a flowchart—Kanan recommends sales orgs invest in a product that’s designed and built for go-to-market teams.

Smooth the Edges

Sales enablement isn’t always a tension-free role. Often, says Kanan, her priorities are at odds with other senior executives. Consider onboarding. Gong’s sales managers may want to minimize ramp up time as much as possible. The sooner a new recruit is on the phones, landing sales and hitting their quota, the better. But for Kanan and other sales enablement professionals, there are other considerations.

“Experience is incredibly important,” she says. “What is someone’s experience when they join the company? Do they feel comfortable? Do they feel welcome? Do they have a home? To me, that’s more important than somebody getting on the phone on day one.”

What complicates the interaction further is that enablement professionals tend to have introverted personalities. They are typically unassuming affiliative leaders, who focus on helping others achieve their goals. Awkward conversations aren’t in their nature. But breaking out of that mindset is essential for high-performing sales enablement professionals, says Kanan. In her roles, having awkward conversations has helped build stronger, more collaborative relationships with previously combative sales leaders. As an industry veteran, Kanan is now happy to sit down with sales leaders and say, “These are my priorities and here’s how it will help your reps but we can’t achieve anything unless we work together.” If aspiring sales enablement professionals want to succeed, she says they must follow her lead.

But sales enablement professionals shouldn’t just wait for conflict to arise. Kanan says enablement must engage sales leadership with the design and implementation of sales enablement projects as soon as possible. Again, consider the onboarding process at Gong. As director of sales enablement, Kanan was the ultimate decision maker but she knew there were other stakeholders, such as sales managers and Gong’s CRO.

“We collected input from all of our stakeholders,” says Kanan, “We never went to market with something that hasn't been seen. The partnership we have with those managers and directors is directly related. We can't be successful if they're not going to champion what we're putting out there.”

However, despite her best efforts, Kanan says that sometimes priorities will conflict and this is a sign of a confused overall strategy. The best way to cultivate a harmonious working environment is by aligning strategic visions early on and realigning regularly. Yet this almost never happens.

“Most sales enablement professionals allow their vice president of sales or CRO to dictate the enablement strategy to them,” she says. “They don’t have enough confidence to go in, own the strategy, and ask for empowerment.”

In other words, enablement professionals must take ownership of their role and set the direction of enablement in their organization. Often, taking control comes down to education. Whenever she experiences pushback on her work, Kanan focuses on education, reaching out to stakeholders to explain what it is she does and what she hopes to achieve. When people see the goals of sales enablement—creating a better, more productive salesforce—few maintain their opposition.

Sales Enablement Yardstick

With the sales enablement role requiring whoever holds it to be engaged on so many different fronts, it can be difficult to gauge that person’s overall success or failure. But with the right balance of general metrics and specific KPIs, Kanan says executives can accurately track the results enablement work is driving.

At the forefront are standard metrics like ramp time and time to first deal, which measure how fast an organization can turn a fresh recruit into a quota-carrying sales professional. These metrics are easy to obtain and are usually fairly accurate, but they only give you a general feel for how things are going. With just these broad metrics, it’s impossible to track the effectiveness of individual campaigns, strategies, or initiatives.

A quote from Michelle Kanan reading "Make sure that you have a goal in mind and a problem that you're trying to solve for every project you run"

For more specific analysis, Kanan recommends sales orgs adopt a project-by-project approach to analysis. “Make sure that you have a goal in mind and a problem that you're trying to solve for every project you run,” Kanan says. Once you have a goal, it’s usually fairly easy to pick a specific metric to track. If Kanan ran a new training course on cold outreach emails, she might track the average win rate of outbound sales. If she implemented a new experience-focused onboarding process, she might track employee satisfaction scores.

But alongside results, Kanan says she also has to measure adoption. In other words, are Gong’s SDRs and AEs actually using the sales training that Kanan delivered. For this question, Kanan turned to the very product she’s employed to sell—Gong. “For all our [sales enablement] initiatives, we build those trackers into Gong and capture the talk tracks that are associated with that initiative,” Kanan says. Then Gong’s sales managers analyze each track for adoption.

But adoption also isn’t an exact science. Sales conversations take unexpected turns so it’s up to the sales managers to interpret what they’re hearing. “It's not black or white,” says Kanan. “A lot of the time, we’re asking, ‘Can we see the momentum and do we see the tide changing from that perspective?’”

Don’t Stop at Sales

As sales enablement has evolved from unloved niche role into a respected, if still developing, sales profession, Kanan’s perception of enablement in general has also changed. She no longer sees enablement as one generalist whole. Now, she advocates for specialized enablement hires as soon as a sales org is large enough. “Once you have several different departments, you need to hire more enablement professionals,” Kanan says.

As Gong continues to grow, Kanan says she’ll continue to expand her enablement team, not just within the sales org but within the larger leadership group, too. “To build a great team, you can’t discount enablement as a checkbox hire,” Kanan says. “You must see and use them as a strategic partner.”