Primary Advisory Session: How to Motivate a Sales Team

You’ve hired a team of hustlers, they’ve all drank the Kool-Aid, they believe your product is the best on the market, and they’re willing to go the extra mile to spread the gospel. Everyone would like to think that’s how their sales team operates; in fact, hiring for passion and mission alignment is critical. But as four sales leaders from the NYC Tech community sat around a table at this week’s Primary Advisory Session, they drilled home the point that salespeople are competitive beasts who are, more often than not, coin-operated. You show them the money, they’ll deliver your desired results. 

The question of how to best motivate a sales team spurred lively conversation. Around the table sat Bryan Rutcofsky, VP of Sales at Yext, Sam Jacobs, SVP of Sales & Marketing at Livestream, Michael Manne, VP of Sales at Namely, and Max Appelbaum, former SVP of Sales & Account Services at Shoptiques, and Director of Inside Sales at SinglePlatform. Collectively, their main takeaway was that it’s nice to think of your team as motivated by a true belief in your company’s mission, but as sales teams scale past the first 10 players or so, it becomes increasingly difficult to lead by passion and mission alone.

How to keep your sales team motivated, in 8 steps or less

1) Hold regular sales contests and accelerators. Regular competitions go a long way toward motivating salespeople to produce their best. For SDRs, you can maximize engagement by holding shorter-term monthly contests, and for AEs, quarterly contests with more ambitious goals are the ticket. Michael Manne warns, however, that you have to be focused when running contests; be sure to incentivize the right behaviors to hit your strategic goals.

2) Set aggressive goals, then challenge your best team members to go even further. Bryan Rutcofsky consistently runs accelerators to drive his top people to produce more - and he insists that they be rewarded not in cash, but in gifts or tangible experiences, like weekends away or splurge dinners. The biggest motivator behind these accelerators is to prove to the team that they are capable of accomplishing more than they believed they could.

3) Insist on clear and public commitments.Every team member should articulate a clear commitment to a number he’ll deliver in every measurement period. Commitments should be stated publicly to increase accountability.

4) Never skip the daily huddle. Sales teams should be accountable to each other and their leaders on a daily basis. Sam Jacobs runs his daily standup at 8:52 every morning (“The odd start time makes people much more focused on punctuality,” he says). The 8-minute meeting enables leaders to identify early indicators of underperformance long before they start to jeopardize the monthly number.

5) Celebrate success publicly. One of the most powerful motivators is public acknowledgement of success. Call out top performers at company meetings and town halls, have a visible leader board that draws attention to team members’ achievements, or blare an obnoxious foghorn when someone scores a big win. Few things scream success more than irritating your officemates...

6) Over-communicate your vision and broader company goals.Sure, these guys may be coin-operated mercenaries, but they also need to understand the big picture. Helping team members see how what they’re doing plays into the big picture will drive motivation at both the team and individual level.

7) Have zero tolerance for marginal attitudes. Sales teams thrive on positive energy and culture. A team member who delivers her numbers consistently but has a negative attitude will have a deleterious impact the collective vibe. Extract that individual and move on quickly.

8) Always be hiring. Once you’ve scaled past the first few salespeople, maintain a consistent hiring pipeline, as you’ll need to perpetually add staff to support growth, churn out poor performers and build a compelling professional development path.

While much of the advisory session focused on driving accountability and motivation through clear goals, tight management and compensation, especially as your team scales, it’s important not to lose sight of culture and mission as strong motivators. Max Appelbaum, who ran one of the biggest sales machines in NYC at SinglePlatform/ConstantContact, emphasized that culture starts in the interview. “Sales is a hard job, and if someone’s going to succeed, they need to truly believe that what they’re selling is going to be an enormous benefit to the customer. From day one, help your team understand why your product is the equivalent of the cure for cancer for your target customers. It’s that sense of belief in what they’re selling that will sustain your people through the frequent drudgery of the sales process.”

Finding the right recipe for continued engagement will vary by team, sales motivation, at its core, starts with hiring people who share your company’s mission and values, and are willing to go the extra mile to meet and exceed their quotas.