Chapter 10

Uncovering Sales Leaders

Creating stepping stones to sales leadership with player-coaches.

When Lorry Destainville joined Q&A platform Quora as its Head of Advertising Sales and Partnerships in June 2017, he found himself looking at a blank slate.

The California-based platform had only rolled out on-site advertising the year before, and its advertising sales team comprised just five employees. In his new role, Destainville was tasked with not only getting the new ad platform off the ground, but building a sales team to support it.

Over the next two years, Destainville worked tirelessly to develop Quora’s sales organization, growing his team to more than 30 managers and individual contributors (ICs). But expansion brought growing pains. As Destainville’s team expanded and clustered into new subteams, the demands of people management grew, which pulled him away from the strategic work he was hired to do.

Without the budget to hire dozens of new sales managers and a growing need to support younger, more inexperienced sellers, Destainville turned to an old management play called the player-coach. While he says these hybrid seller-managers are never the ideal solution, it allowed him to quickly augment his leadership team and create an internal path to sales leadership, empowering ambitious ICs to soar through the ranks.

Putting Together the Right Team

Destainville cut his teeth in high-growth technology companies. He was a growth analyst at Myspace during its boom years and an account strategist at Facebook as it transitioned from scrappy startup to tech conglomerate. When he arrived at Quora, he had already seen how large companies structure their sales orgs for maximum efficiency. Instead of reinventing the wheel, he took the best ideas he had seen at Facebook and Google and adapted them for Quora’s specific needs.

“Our team is structured in three groups,” Destainville tells 360Learning. “You have new business, customer success, and scaled operations.”

The first group, new business, is tasked with identifying and recruiting enterprise advertisers. The second group, customer success, is there to support large customers once they’re signed up. And the third group, scaled operations, helps Quora’s self-service advertising customers.

When Destainville joined Quora, he had the basic blueprint for how to build a sales org, but he had to figure out how to apply it at his new company. “It was unclear to us whether we would need one or two customer success managers per account executive,” he says. “We were still working towards a better understanding of capacity.”

Growth was slow in the beginning, with Destainville adding roles as and when he needed them. But as the team crept past the 12-person mark, it became more unwieldy. As teams grow, more and more people need support and that demands a support structure, not just a single person. He found he was dedicating a huge chunk of his time to people management, leaving precious few hours for strategic planning. Something had to change.

Destainville knew he needed help leading the three sales teams, and he was acutely aware of the importance of hiring the right leaders, people who would amplify Quora’s desired culture rather than introducing brand new values. If he brought in a disruptive sales manager at such an early point in the sales org’s existence, it could set the team back months.

He also recognized that he was creating a new type of role in the sales org. “Becoming a sales manager isn’t just climbing the next rung on the ladder—it’s an entirely different role with a much different skill set,” says Destainville. “Some of the best sales managers are definitely not the best sellers. Likewise, I've seen great sales reps struggle with people management.”

Since Quora had only a small pool of sales professionals, most of them ICs with limited managerial experience, Destainville initially opted against hiring internally. “I decided to hire managers with people management experience,” he says. Bringing in experienced sales managers gave each team a confident and competent figurehead, and provided the stability needed to help ICs work with confidence. It also allowed Destainville to step back from the day-to-day demands of management and focus on the bigger picture.

For a while, Destainville was happy with the composition of the team. Sales were improving, brand awareness was increasing, and everything seemed to be going well. But as Quora’s advertising platform gained steam and the sales team continued growing, the burden of people management again became too much to bear. There were too many call reviews, coaching sessions, and employee reviews for his leadership team to handle.

This time, Destainville couldn’t just bring in a specialized external hire. He was already at the limits of his prescribed headcount, and he didn’t have the budget to bring in new sales managers. He knew that a solution was going to have to come from within.

A quote from Lorry Destainville reading "There's a very big differentiation to be made when it comes to sales and sales management."

Stepping Stones to Leadership

Without the budget to hire additional managers, Destainville looked to the army of talented sales professionals he’d hired over the past year. But he faced the same problem as before: most of his ICs had little experience managing people. He needed experienced sellers to start managing people and bring in revenue at the same time and that needed was a stepping stone position—a way of learning on the job.

To expand his leadership team without losing revenue, Destainville borrowed an old management idea—the “player-coach.” The player-coach is someone whose responsibilities include both people management and their own deliverables. “What that means in practice,” he says, “is an experienced seller who manages more junior sellers and carries their own book of business.”

Destainville believed the idea would be attractive to both ICs and management. Existing managers could transfer much of their people management work—call reviews, coaching, roleplays, and so on—to the new player-coaches, freeing up time for higher-value activities. For ICs, becoming a player-coach represented the first step towards sales leadership. It provided a controlled environment in which to learn, practice, and hone new management skills like communication, coaching, and analysis. But it wasn’t designed to be a cushy ride.

“It's a challenging role,” Destainville says of player-coaches. “Sellers need to create their own pipeline and deliver on their quotas and do a good job at coaching folks, too.”

When it came time to start recruiting for the new roles, Destainville quickly discovered that identifying quality applicants was trickier than expected. “You find people who are sellers at heart,” he says. “That's where they get their energy, that's what they thrive in. Those folks may not be the best fit for sales leadership.”

Destainville discounted the career sellers who weren’t interested in the role, and also all the inexperienced sellers who weren’t equipped for it. With a small pool of qualified applicants, Destainville started approaching potential player-coaches and pitching them on the role.

Uptake was slow but steady, and over time Destainville gradually built out a network of excellent player-coaches, all of whom knew the sales industry like the back of their hand and wanted to transfer that knowledge onto the next generation of sales professionals. With these individuals trained and ready, much of Quora’s sales coaching is now handled by Destainville’s team of player-coaches. They listen to sales calls, analyze outreach emails, and monitor quota attainment. Whenever they see an opportunity to provide value to an account executive or success manager, they reach out with hands-on coaching.

All the while, player-coaches are acquiring valuable people management skills and preparing themselves for the next step in their career. And when a fully-fledged sales management role opens up, Destainville says he is eager to consider applications from player-coaches.

While Quora’s player-coach position emerged from budget constraints, it has evolved into a highly valued element of the sales org’s structure. It creates an effective internal pipeline for sales leadership, accepting ambitious reps, and outputting talented leaders.

Uncovering Leadership Potential

Although it sounds straightforward, building a team of half-sellers, half-managers isn’t exactly easy. Consider a great basketball coach, Destainville says. What makes them great at their job?

First, a great coach must understand the game of basketball. They need to understand the advantages of zone defence and the drawbacks of man-on-man. If they don’t have an in-depth understanding of the game, they don’t have the knowledge and skills to transfer to their students.

Second, a coach also needs to be a great teacher. They must be highly empathetic so they understand their player’s struggles. They must be patient so they don’t get stressed when a player fails to grasp a complex strategy. And they must be passionate so the demands of coaching don’t wear them down.

With these qualities, a coach can stand up in the locker room, unveiling complex plays on a whiteboard and transferring their knowledge to their players. And the same is true for sales leaders.

Just like a great math teacher needs to do more than crunch numbers, an effective player-coach needs to do more than just sell. As Destainville says, the best sales leaders aren’t just the best sellers, they are “patient, empathetic, and passionate about teaching,” he says.

But even having the skills and the drive isn’t enough. According to Destainville, while some may view it as a quick jump up the ladder, the player-coach role “isn’t for everyone.” After two years of recruiting and assessing player-coaches, Destainville has a good feel for who will make a successful recruit.

Destainville is quick to note that an applicant’s current coaching resumé isn’t all that relevant. Just because someone teaches piano in the evening or coaches Little League on Sundays doesn’t mean they’ll make a good player-coach in a professional setting. Destainville’s player-coaches have to contribute to sales strategy discussions, advise marketing, and report back to management. They’re not just sellers who do some coaching on the side, they’re asked to demonstrate leadership beyond their immediate people-management responsibilities.

Another strong indicator, Destainville says, is an employee who wants to be part of the leadership conversation. “Wanting to take on a role where there's more of a say into, for example, our go-to market strategy is a good indicator that someone has a greater sense of empathy for folks around them and just a strong desire to help,” he says. It’s the difference between someone who is happy to identify a problem and leave it for others to fix, and someone who can identify a problem and pitch a possible solution.

Finally, Destainville says, there are a handful of personal qualities that not all ICs have. “You need the desire to coach and manage talent,” he says. “Those aren’t desires that all sales reps have or want.” While someone can become a world-class seller without these qualities, they’re necessary in order to succeed in a sales leadership role.

Illustration of a dashboard used to measure the success of sales enablement initiatives

Gauging Success

The player-coach role is inherently challenging, says Destainville. Employees are tasked with performing two distinct jobs—sales rep and the sales manager—and the tension between the two is what makes or breaks someone. It’s not a long-term solution, either. Destainville advises only using player-coaches until you have the budget for dedicated sales leadership hires—and even then only if you are prepared to put in a lot of strategic groundwork.

To stand the best chance of success, sales leaders must align on clear quarterly OKRs, which include both personal and team-wide goals. Typically these goals should include a wide range of metrics, such as revenue, pipeline fulfilment, activity, and new projects, advises Destainville.

Compensation must change, too. When a seller is sacraficing commission-generating selling time to mentor and manage, you must replace that lost income. “Increasing base salaries and decreasing variable compensation makes the player-coach role more appealing to everyone,” says Destainville.

While tweaking their compensation will help player-coaches to change their focus, they often need an extra nudge. “Merge the quarterly revenue or activity goal for the player coach with their reports’ goals,” he says. “It empowers them to better prioritize their time.”

Finally, don’t assume a player-coach will be able to shoulder their increased workload alone. Adding a whole new job to their schedule is demanding and they will almost certainly have to cut some of their previous duties. “Have an SDR support the player-coach,” advises Destainville. “It’s their prospecting time that will most likely be difficult to prioritize over supporting reports or move ongoing conversations forward.”

With the strategic groundwork completed, player-coaches stand the best chance of success—but it’s still not an easy job.

“It’s challenging for them to think about what's the best use of their time, because ultimately that's what it comes down to,” he says. “It requires a ruthless prioritization to determine what's the best way for them to impact the business.”

These competing functions require two separate success criteria.

First, player-coaches are still evaluated as sales reps. At Quora, Destainville still assigns sales quotas and measures his player-coaches’ progress towards them. “You look at your goals for the quarter,” Destainville says, “and you ask the question, ‘Did you meet my expectations? Yes or no?’”

If their IC performance hits the mark, Destainville then evaluates his player-coaches using the same success criteria as his regular sales managers. Did they increase performance from their direct reports? Was their forecasting accurate? Was the qualitative feedback from Quora’s sales reps positive? Did they contribute to Quora’s sales overarching strategy?

Sometimes, the step up doesn’t work out. “People may get excited about the idea,” explains Destainville. They may misjudge the increased workload or ignore shift in focus. When this happens, Destainville is quick to offer them a route back to their IC role. But he doesn’t see these mistakes as failures—and neither should other sales leaders. Almost any sales leader will make a handful of ill-fated sales management promotions over the course of their career. It’s through these mistakes that they discover the key differences between excelling in sales and excelling as a sales leader.

But when a player-coach promotion does work out, it’s hugely beneficial for a sales org.

From the perspective of a sales rep, they get a coach and mentor who understands their challenges, objectives and goals better than most. And their coach works right alongside them every day. If they need advice or help, they don’t need to wait for a weekly coaching session. They can swivel their chair and ask their coach directly.

For the senior sales leadership, creating player-coaching roles helps, too. As sales orgs grow, the leadership demands grow exponentially. Sharing the coaching burdens with other employees means senior leaders can free up huge swathes of their time to devote their time to higher level work like strategy planning.

And for the player-coach, the half-step promotion offers an opportunity to flex and refine their leadership skills in a controlled environment. They can practice running call reviews, experiment with feedback styles, and improve their forecasting—all on a small, controlled scale. When a fully fledged sales leadership position opens up, they’re ready to take it on because they already done the job on a smaller scale.