Meet WoodmenLife’s August 2025 Sure Start Winner: Dustin Cunningham

WoodmenLife is committed to offering training to our Sales Representatives to help them grow and have the tools they need to best serve our members. Qualifying new full-time Representatives are invited to Sure Start, an interactive training event that helps them kick off their careers with WoodmenLife. During the 12 months following their Sure Start education, these Representatives have a friendly competition with their classmates to see how well they put their lessons into action and compare their sales achievements.

Get to know our August 2025 Sure Start Winner: Dustin Cunningham of Columbus, KY.

Congratulations on your Sure Start victory! How did you celebrate?

I first learned through my Recruiting Sales Manager Ricky Willis. We had a good time celebrating the win. I also went home to share the news with my wife and kids — everyone was so proud and excited. It truly is a once-in-a-lifetime opportunity, and I am very proud I accomplished it.

What inspired you to choose a career with WoodmenLife?

I was looking for something different that allowed more freedom with my family. My wife talked to the Sales Representative we went through to purchase life insurance, and she recommended WoodmenLife. I met with Ricky Willis and Regional Director Greg Robertson on the same day, enjoyed the conversations we had, and followed up with Ricky a few times after. He really sold me on WoodmenLife and the opportunities, benefits, and possibilities that come with this job.

Have you always wanted to pursue a career in sales?

Absolutely not! I was not at all looking at anything close to this. Nevertheless, here we are.

What drives you to deliver great service for your members?

I do not treat our members as dollar signs. I genuinely believe that there is something special in the relationships built through our business. We’re not making a sale, then never communicating with our members again. Rather, we’re staying in touch with them and “treating them as I would want to be treated” — plus more.

Why is community outreach so important to you?

Being present for the community is important to gain trust, build relationships, and show compassion. It is a blessing to see my members out in the community and discuss life with them — and even to meet potential members who I might be able to help in the future and can start building relationships with.

Do you have a particularly memorable moment from your time so far with WoodmenLife?

When I first joined WoodmenLife, when I earned a place on the Incentive Trip, and when I won Sure Start, the first person to cheer me on and encourage me was my Recruiting Sales Manager Ricky Willis. I definitely could not have made it where I am today without him.

Also, my wife has supported me from day one. I appreciate the words of wisdom she shared one night, instilling in me how important it was to take care of people through this career. I will always hold that with me.

What are your goals for the future?

I will strive to better myself as a Sales Representative. With each passing year, I aim to grow more in my knowledge about our business and be ready to help people in every possible way.

Read More

Meet WoodmenLife’s July 2025 Sure Start Winner: Graden Lowry

Meet WoodmenLife’s September 2025 Sure Start Winner: Mike Wicker

WEB889