Episode OneHundredEighteen

How to Harvest Your Unique Qualities for Sales Success

Guest: Kyle Willis, Director of Sales Development at Directive

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About This Episode

What’s an entry level SDR doing texting C-suite executives?

Just showing immense confidence and authenticity, that’s all.

Recently, I got to talk with Kyle Willis, Director of Sales Development at Directive, about how to harvest your unique qualities to become successful in sales.

The world is full of noise, but if you can be authentic and unique, that can become one of your biggest moats in business.

Yet Kyle says he’s not unique. “Every human has a story, and mine just happened to play out the way that it has,” he said.

He started his first business in high school printing apparel, saw it grow throughout college, and got into real estate after a 3,000 mile move to California. Where he became a fitness model.

And learned how to text C-suite executives.

Learning to Catch the Ball & Text the Execs

Kyle wanted to play catch with his older brother, but if Kyle dropped the pass, his brother would go inside. “I really wanted to play with him, and so I had to earn my keep,” Kyle said.

“You develop this ‘prove people wrong’ mentality. When it comes to sales, we have a lot of leaders in our space who have a tendency to call out sales reps and thinking that there isn’t enough confidence in our arena to reach out to the C-suite if you’re an entry level SDR,” he said.

The truth is that all it takes is confidence.

“In regards to text, I just try to bring humanity into sales,” Kyle said.

The sales process has gotten extremely robotic across many different verticals — and people don’t want that.

To earn the right to text, you have to be authentic first.

“You want to start to build that relationship before you j start hitting up someone’s mobile phone,” he said.

P.S.: Authenticity includes owning it when you trip up. One of Kyle’s favorite tips for calling executives is, after they’ve said no, to ask what he could have done that would have resulted in a meeting.

Texting Best Practices

  • Never a first touch
  • Use it to build authentic relationships
  • Add value (even if it’s just getting them to laugh)
  • People will sometimes answer an email with a text

Determination Is Jumping on a Pogo Stick for an Hour

Teenage Kyle really wanted a dirt bike. Like, really, really wanted one.

Well, his mom called his bluff on whether he could jump on a Pogo stick for an hour. So there he was in the driveway, jumping on a Pogo stick for all he was worth.

“Long story short, yeah, an hour later, my mom’s like, you did it, you did it! And then I literally fell off the Pogo stick on my back in tears of joy,” he said.

That determination is what it takes to be successful in sales. 


“We don’t give enough credence to the power of visualization,” Kyle said. He could see himself on the dirt bike, knew what it would feel like and what he would do.

Small Wins

You might not book the meeting, but small wins will raise your confidence. You’ll be hearing No 99% of the time, so you can’t rest all your self-esteem on Yes.

“Maybe it’s just a good conversation with someone. Maybe it’s making someone laugh. Maybe it’s getting a little bit more information about where they’re currently at,” Kyle said.


“If you can see it, you can get it,” he said. “It sometimes takes a lot more than you realized you had to offer.”

Focus on the small things versus I didn’t get the meeting.

Sales Is Like Personal Fitness

So, Kyle was featured on the cover of Men’s Fitness.

Battling chronic Lyme disease for 10 years, he decided to commit himself to taking his health extremely seriously: nutrition, exercise, water intake, rest.

That’s where it started. At 5:00 AM in the gym, every day.

“It was this discipline that I developed, and now it’s a part of my day to day,” Kyle said.

In the course of that discipline, people approached him and asked about health. One person suggested modeling. He found a photographer on Craigslist and put together a portfolio.

It was networking and seeking opportunities. But before all of that, it was dedication and drive.

“If you can get yourself into the gym at 5:00 AM every single morning, I know for a fact you can be a successful SDR,” Kyle said.

“There is something to be said about building yourself up. When you feel confident, that confidence absolutely is pushed through that channel,” he said.

Making 75 to 100 dials a day isn’t the easiest thing in the world to do. But you know what you’re working towards. 

Same with fitness. People who see extraordinary results are extremely disciplined. If you can stick to your sales schedule consistently and confidently, regardless of how difficult it is, you will be successful.

“That’s what fitness has shown me — persistence, perseverance, and the willingness to win,” he said.

This is an interview with Kyle Willis from Directive.

To hear this episode and many more like it, you can 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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