How to Scale a World-Class Sales Team

In our latest Tout Live event in association with Enterprise Sales Meetup and Sales Hacker, we brought together Lesley Young, SVP of Commercial Sales and Sales Operations at Box and Frank Swain, Chief Revenue Officer at ToutApp, to talk about their experiences in scaling Sales teams.

The night’s talk covered topics such as metrics, sales methodologies and the importance of building a repeatable sales process. But, the one thing that both Lesley and Frank discussed most was the importance of building a strong Sales team that’s designed to go after larger deals, do more and scale. We’re sharing with you key takeaways and quotes from the event below. 

Create a Hiring Rubric

“The biggest challenge in bringing on people fast is you have to make sure you maintain the quality of the success criteria and not give that up. And that’s really hard when you’re use pressure to meet numbers,” said Lesley Young.

Hiring good Salespeople is tough. In a job market where good Salespeople are in high demand, it can be detrimental to companies that hire too many reps, too fast and dilute the quality of good sales just to scramble to meet their numbers.


Frank Swain, Lesley Young and Mark Birch.

For both Frank and Leslie, the first order of business when hiring reps begins with having a rubric or an Ideal Candidate Profile.

“The main thing I’ve learned from the past three to four companies is, as you start to grow and scale, it breaks down. It’s important that you have a process around screening and hiring your candidates,” said Frank Swain.

Frank believes in having a defined Ideal Candidate Profile for every Sales role within the larger organization and looks for three main characteristics in every candidate:

  1. Intelligence
  2. Strong character
  3. Drive

“If you hire people who have drive, they’re going to be just as hard on themselves as any manager. So, it’s really important to bring the right folks into the organization,” said Frank.

Hiring reps with the trifecta of characteristics will not only lead to high-performance and scalability, but more importantly it will transform your business from $0 to $X million.

Invest in Onboarding and Sales Enablement

Bringing on the right reps is only the first phase in scaling a sales team. The second phase is bringing them on, giving them proper onboarding and continual support throughout the sales process via Sales Enablement.

“The worst thing you can do is invest all this time into hiring someone, onboarding them through a camp [training] for a week and then put them out on the field where they’re left to their own devices—and six months later they’re not successful,” said Lesley.

Bringing a rep on and onboarding them costs a lot of money. Failure to do so results in rep turnover at a higher rate—which hinders an organization’s ability to scale and wastes company money.

Much like onboarding customer and ensuring that they’re successful on your platform, the same strategy must be applied to your Sales team. The money that your company has invested in hiring the rep, onboarding and training shouldn’t be a wasted effort, rather it needs to yield a return in revenue.

Implementing a Sales Enablement program, even at the early stages of companies will allows you to train reps, retain them and scale the team properly. Whether it’s rolling out an intensive five-day training “sales camp” like Box or a rigorous program that’s rolled out over a series a weeks that’s focused on a singular skill like ToutApp—training and enablement is a must.  

“I learned this part the hard way by not having a rigid Sales Enablement program in the early stages of the companies that I’ve been involved in,” said Frank. “What ends of up happening is I run around trying to get all the deals closed at the end of the quarter.”

Have a Culture of Clear Expectations

According to Gallup, “a sales force is built on the capabilities of its managers. Front-line supervisors play a key role in influencing the performance of the Salespeople they manage and motivate.” This means that it’s a manager’s responsibility to manage and cultivate a culture of clear expectations that drives towards peak performance.

“You have to create a culture where success is celebrated. Ring the Sales Gong and make a big deal about all the wins,” said Frank. “But, you also have to set attainable goals. If you set a goal that no one is going to reach—no one’s going to be motivated.”

If a rep is doing a great job, the team should celebrate those wins. If a rep isn’t on track to meeting their goals, the manager and rep should work together to get them on track. Sales is about your number—and every Sales Leader must set clear expectations with their reps on that number.

“If you build the right kind of culture, people will do their own whip cracking. You have to be clear on what the expectations are and when someone goes off track, you bring them back on track, and if it’s not working—it’s clear,” said Lesley.

Scaling a sales team is a huge task. And it takes more than these three steps—but if you follow these steps from our experienced Leaders, you’ll be on the track to scale.

Want More on Scaling Sales Teams?

For full coverage on How to Scale a World Class Sales Team, watch the full-event video with Lesley Young, Frank Swain and moderator Mark Birch here.