Brett Gilbert has been in B2B sales long enough to have seen most playbooks written, and a few rewritten.

Currently the VP Sales at Momentive AI (formerly known as SurveyMonkey), Brett spent over ten years at Salesforce, where he learned how to scale a SaaS business from the ground up.

“Working at Salesforce was like getting a Ph.D. in SaaS,” says Brett.

In his view, Salesforce wrote the playbook on selling, scaling, engaging, and retaining customers for cloud companies.

Brett joined Salesforce right after its IPO and worked his way up as the company scaled from startup to category leader.

Before that, he was at Oracle, Oridus, and ADP.

In this interview with Blaise Bevilacqua, Senior Account Executive at UserGems, Brett covers how he builds high-performing outbound teams, where he focuses targeting to maximize win rates, and the one trait that separates reps who hit quota from those who don't.

Here’s the link to the podcast interview if you prefer to give it a listen. Otherwise, keep reading for the full breakdown.

Editor’s note: The editor has edited and condensed the following for clarity.

Brett Gilbert on Sales Leadership, Targeting, and Grit

The art of sales team management and leadership

Stepping into a sales management role for the first time can be challenging.

Effective sales team management starts with knowing how to sell. Brett believes the best preparation is to get good at selling what your team is selling.

“When I transitioned to a leadership role at Salesforce, knowing how to sell and execute well was a big plus,” Brett explains.

The confidence and credibility that come from knowing how to sell your product goes a long way when motivating and supporting your team. Knowing how to sell your product builds confidence and credibility, regardless of your sales ranking or awards.

“Managing and selling are two different skill sets. Managing and selling call on distinct skill sets, and knowing the craft of selling gives managers a meaningful edge,” says Brett.

“When you don’t know anything about managing and move into a leadership role, you tend to do a lot of hero managing: ‘get me involved in your deal and get out of the way! I know how to do that better than you do.’”

“But the faster you can get out of doing that, the better because a frontline sales leader's role centers on supporting and developing reps,” he continues.

Your most critical sales team management tasks are supporting, motivating, hiring, and developing your reps. “Your job as a leader is to support your reps and help them grow.” says Brett.

Your job is to observe, listen, and remove obstacles—not to close deals for your reps.

Sustaining a competitive advantage

“When it comes to sales prospecting, I think the days of spray and pray are over. We all need to do a better job of being hyper-targeted and specific in our messaging.”

To find the warmest paths into an account, Brett focuses on having a competitive advantage.

“Focus your efforts on the right-fit accounts,” he explains.

The qualification phase is critical in identifying customer fit.

“Certain companies are a strong fit, and others are not worth pursuing. Certain companies will be a better fit for a variety of reasons. You’ve to know what you do well. You have to know where you have a competitive advantage in a deal cycle in terms of acquiring a new customer.”

“You have to figure out where you’re going to provide value to a prospect. Salesforce doesn’t talk to everybody. They talk to customers who are potentially a good fit, such as companies that use cloud services, who might leverage their community or their live agent, who have great Alexa rank scores, and high amounts of page views. That way, they have a competitive advantage [when pitching to those companies],” Brett continues.

The takeaway: know which companies are the right fit, understand why, and build a message specific to their context.

“At Momentive, we’re trying to get more surgical about going into companies with a specific message that we know will interest them based on the kind of company they are, their tech stack, and their industry.

Grit: the most crucial skill no one talks about

As someone who has been around the circuit for a while, Brett has seen enough to know that the sales game isn’t for everyone.

“The most successful people on earth (‘and sales’) always have grit. That’s the number one thing. But it’s almost impossible to truly assess it in an interview,” he explains.

“You have to know (‘and accept’) that you’re going to have peaks and valleys. There’s going to be good months and bad months. And good quarters and bad quarters. And being comfortable with that is important.”

“You need the drive to push through bad months and the discipline to stick to the plan even when results lag,” Brett continues. “You need to have a plan, work the plan, trust the plan, and be willing to adapt the plan if it’s not working. Ultimately, have the confidence that what you’re doing is the right thing to do.”

Brett's parting point:

“Remember, the grit that got you here will keep you successful in your career.”

Full interview: The First 100 Days podcast