Episode OneHundredEightyEight

How to Win at Your Team’s Personal Development

Guest: Drake Duenas, Business Development Leader at Vertafore

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About This Episode

There’s a crucial difference between management and leadership.

Management focuses on the numbers, while leadership focuses on the people.

I loved hearing from Drake Duenas, Business Development Leader at Vertafore, about the joy he takes in cheerleading his sales team.

“When you focus on not just professional development, but on the personal development of everyone on your team, they’re better able to focus on their customers and hitting their numbers,” Drake said.

Drake’s leadership focuses on developing the whole person and building relationships — and he shares his call coaching tips, too.

People matter more than metrics

It’s not that the number isn’t important, because it is.

But if all you focus on is numbers, opportunities, or bookings, you lose sight of the employee as a whole.

“If we can focus on a well-rounded employee, they’re going to take care of their customers and they’re going to drive that number,” Drake said.

Leadership to Drake is caring about your employees. The numbers, revenue, and quota are almost byproducts of supporting your team.

If employees enjoy coming into work every day, the customers will be happy, too.

1. Build relationship first

Saying you care about your employees isn’t nearly enough. You have to put it into practice.

Before you dive into metrics in a 1-on-1, try asking how their life is going.

“Can we actually take a step back and get to know each other a little bit and to have an actual personal relationship?” Drake asked.

He challenged leaders to be authentic by asking about their employees’ lives. 

2. Feedback, not criticism

“When you show the individuals that you work with that you care about them and their career, that also opens the door for some really honest feedback,” Drake pointed out.

People are way more likely to accept coaching and feedback if it comes from a person who genuinely wants to improve their game.

Feedback is more effective when it comes from a position of caring.

3. Investing in the future

Drake was beside himself with excitement about something that most business development leaders dread: reps leaving.

Whether through promotion or changing companies, most reps only stay for 6, 12, or 18 months.

But Drake views his role in their personal and professional development as making the whole industry better.

“It’s so cool that I get to focus on not just developing opportunity for the business, but also developing future leaders and talent,” Drake said.

Training strategies

Things that a manager tells you vs. things that you learn from your peers…

“Group learning is incredibly imperative to the success of my team,” Drake said.

He seeks opportunities for team leads or experienced reps to impart their knowledge to his teams.

When reps who have started to gain confidence in their role start to share talk tracks and give each other feedback, that’s a sign of a culture of caring.

Drake wants to create a safe space full of people who care about each other’s successes. “We don’t want to criticize, we just want to share feedback. We want to help everyone around us,” he said.

Weekly call coaching

Drake meets with team leads weekly on Wednesdays at 2:00. They focus on a specific topic (intros, voicemails, setting next steps, etc.) that recycle every 6 to 12 weeks.

The group learning feedback comes not just from Drake but from the other team leads in the room (or Zoom call). 

People leaving the team is an indicator of success. “People are entering into that next phase of their career better prepared because they’re doing that group learning exercise,” he said.

He also does 1-on-1 coaching, of course, but the Wednesday meeting is the cornerstone of accelerated learning.

Drake has the mindset of always learning, too. “I’m lucky that I get to go to work and learn something new every day,” he said.

This philosophy of perpetual learning in leadership has created a lot of professional connections for him that he believes will keep him in leadership for the rest of his career.

Cheerleading your team

Some advice that Drake received before his current position has shaped his outlook on his work: “A huge part of your job is being a cheerleader for the people around you.”

“I love being a positive force on my team to get people motivated to do their jobs,” he said. “That part of it’s been a ton of fun.”

Hitting your individual quota feels great, but helping people become better at hitting their own quotas conveys a sense of purpose and fulfillment that goes beyond your own success.

The most fulfilling meetings aren’t the ones about call coaching or products. They’re about helping a rep prepare for an interview or charting strengths that developed over the past year.


Good leadership boils down to authenticity.

“If I walk into a team meeting or a call coaching session and pretend like I know everything and pretend like I’m perfect, it’s not authentic,” Drake observed.

Leaders should open themselves up to honest feedback, too. Asking for insight on how to improve as a leader reaffirms the relationship that should be the foundation of coaching in the first place.

I ended by asking Drake the one piece of advice that he’d like to share.

“There’s a difference between top down management, focusing on metrics, and the leadership where you’re actually caring about the whole person,” he said.

Caring about both personal and professional development means you want to create a well-rounded employee. 

“If you can be a successful leader and care about your employees, that’s actually going to drive results for your company and for the customers that you serve,” Drake said.

For more engaging sales conversations, subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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