Instilling a Culture of Sales Performance

Sales can be a lonely profession. Reps usually work alone and are expected to deliver hard results. While some reps thrive in this lone-wolf culture, forward-thinking sales leaders often look for ways to create a vibrant team culture and drive high-performance teamwide.

But cultivating sales success is easier said than done. It’s a complex puzzle for sales leaders to figure out which inputs will lead to the best bottom-line outputs. Increasingly, sales teams are focusing on—and investing in—training and enablement to build a healthy culture and empower reps to succeed.

But don’t take our word for it—we wanted to see how a real leader transformed the trajectory of their team through thoughtful enablement. Kevin Dorsey, Head of Sales Development and Enablement at ServiceTitan built numerous sales teams from the ground up before he was tapped to revitalize the ServiceTitan sales team. He offered three insights for instilling and scaling a new culture of enablement in a sales org:

Culture is the foundation of transformational change

Culture is, by nature, unique to every company and team—and it can be a remarkable asset or a significant challenge. Kevin believes that certain traits are important for a vibrant sales team. “What I’ve learned is…if I can get a culture of development, a culture of learning, and a culture of excellence—then I start introducing processes—people are actually excited for that.”

But Kevin couldn’t simply declare a new sales culture—he needed to slowly turn the ship towards a new standard of growth and excellence. So when joined ServiceTitan, he invested significant time with his team:

“I had one-on-ones with every single rep on the team. It was focused on why they started here, what they were hoping for, and what kind of culture they wanted to be part of.”—Kevin Dorsey

The focus on individual people cultivated trust from Kevin’s team members. The reps felt ownership of the cultural shift and were committed to his vision of a learning culture. Building a high-performing culture isn’t for those looking for instantaneous results. It takes time, effort, and energy to create a sustainable sales organization that will consistently deliver results—quarter after quarter.

It’s time to redefine sales enablement

Kevin’s secret weapon for cultural change is training and enablement. He notes, “I’m a big believer in the 80/20 rule—80% of your results come from 20% of your activities. I believe a significant part of the results we create are from enablement.”

While most sales leaders say that training and enablement are important to them, Kevin believes that, in many cases, they’re simply paying lip service. Great enablement isn’t about producing more materials—it’s about delivering results.

To highlight this principle, Kevin adds, “As enablement leaders, I believe we need to change the word enablement into performance. If you can’t improve performance, the role and departments won’t exist.”
While this may seem dire, this perspective offers a return to the roots of sales enablement: enabling sales reps to do better work.

Metrics empower meaningful enablement

While culture may be shifting towards learning and performance, how does a sales leader encourage that change operationally? Kevin leaned on individual rep metrics as a barometer for improvement:

“I broke down each thing I wanted sales reps to do, prioritized it, and broke them down into individual metrics. I said, ‘If you want to hit your quota, this is what you have to do—it’s basic math.”—Kevin Dorsey

Kevin identified numerous metrics and created CRM reporting dials for each rep on each measure. He then designed training to impact each ratio: addressing qualification, conversion, closed deals, and more. His refrain for measuring the impact of training was simple: “If you’re truly enabling the team, I should be able to measure it.”
“We don’t like signing up to be measured,” Kevin notes. But as the adage goes—what gets measured get managed. When sales enablement leaders lean into metrics, as opposed to avoiding them, they can intentionally improve the performance of their teams.

Looking to the future

These strategies have worked wonders for Kevin’s team at ServiceTitan, and he notes, “In the last six months, every measurable metric in my department has gone up. Every single one.”

While he wants to create a winning team, Kevin is also thinking about the bigger picture—the future of sales depends on great enablement. With the rise of AI tools in sales, “If we ignore the performance side of things, if reps don’t get better, robots will replace us,” he predicts.

So what is the answer to emerging technologies with the potential to disrupt sales? You guessed it—training and development. Reps who want to succeed in the years ahead must be willing to grow, learn endlessly, and continue to find ways to contribute in ways that are uniquely human—an invaluable combination for long-run sales success.

Supercharge training and enablement with Lessonly

Hundreds of sales leaders use Lessonly to enable learning, practice, and performance on their teams. Managers and trainers create intuitive lessons in minutes and deploy them at scale. The results? Better training, happier employees, and more closed deals. Tour Lessonly today.

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