Brett Gilbert is an OG in the B2B sales world.

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 had joined Salesforce right after its IPO. He experienced the company’s meteoric rise to category leader while working his way up from a General Business Account Executive to AVP Sales, Healthcare & Life Sciences vertical in five years.

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

In this interview with Blaise Bevilacqua, Senior Account Executive at UserGems, he talks about leading sales teams, gaining a competitive edge in the B2B marketplace, and the most crucial quality for professional success (not found on a resume).

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

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

The art of managing and leading a sales team

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

To manage the complexities of leading a sales team, Brett believes the best form of 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. This doesn’t mean you need to sell the most products or win the top seller award. 

That would be great, though.

“Managing and selling are two different skill sets. The best sellers are not always the best managers. But it does help to know the tricks of the trade,” 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 that’s not the role of a frontline sales leader,” he continues.

Your most critical leadership tasks are supporting, motivating, hiring, and developing your reps. “Your job as a leader is not to do their jobs for them, but to support them and help them grow,” says Brett.

Be another set of 👀. and👂

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.

“You can’t go after everyone,” he explains.

The qualification phase is critical in identifying customer fit.

“Everybody isn’t a good fit. 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 —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.

Bottom line: delivering a targeted message that speaks to your customers’ world is critical to success.

“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 gotta have that hustle, fight and a take-no-prisoners attitude,” 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 rounds up with this final piece of advice:

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

Listen to the full interview with Brett on The First 100 Days podcast