Episode 3: Act with Intent | Dwight Henderson

This week JR and John sit down with one of JR’s former colleagues at Turbonomic to talk about what put Dwight on a path to sales and to dig in on all the work that he puts in to influence where his path leads.

Dwight Henderson, former Dickinson College lacrosse player and current Commercial Sales Manager at Workato, is a thinker. He approaches his life and his work in a very deliberate and measured way, which reminds us that no single type of person or personality is a requirement to be successful in sales.

You Have to Like It

As a kid, Dwight was a baseball guy. That’s what his dad played, that’s what he played. But Dwight couldn’t stand it and did what very few 7th graders would dare do—he told his dad the truth and asked to try something new. Enter lacrosse, which took Dwight through high school and on to a prolific career at Dickinson College. About four or five games into his college career, his coach and mentor asked Dwight to switch positions, for the greater good of the team. Dwight did, and Dickinson had some extremely impressive win-loss records during his time on the team. He was a team player, driven, steady, and hardworking. As we hear from most former college athletes, the relationships with his teammates are among the more valuable relationships in his life to this day.

Finding Your Career

Finding your career means finding yourself. When it came time to think about life beyond college Dwight brainstormed about what he liked, what skills he had, where he might use them, and how they might translate in different ways. Knowing a bit more about what he did and didn’t want was particularly helpful in a conversation that led to an internship before his senior year. He spent the summer doing research on LinkedIn, identifying prospects, and populating spreadsheets. He could see and feel the excitement all around him—he was hooked.

Inform Your Choices

When you’re first starting out, it’s hard to know what to do. Dwight advises that you get yourself well-prepared, particularly to understand how your skills translate to the role, to turn that relationship into a strong story, and to have good examples to illustrate your points. Once your story is written, cast a wide net at all kinds of tech companies with all degrees of trajectory, and then tell that story to as many people as you can. Keep telling it until you find something that feels well-aligned with who you are and what you want.

Specifically, Dwight suggests evaluating three things when considering a company:

1. Who you will be working for—do you feel they are bought-into your success and will offer you the teaching/coaching/mentoring you need?
2. The product—do you understand why customers and consumers buy and use it, and do you think you could sell it?
3. Your objectives—do you see how the company/team/opportunity will help you get to your next goal, whatever that is? It’s going to be really, really hard work no matter what, so you might as well set yourself up for success.

20/20 Hindsight

When Dwight looks back, here’s what he wants you to know:

1. Start early, evaluate your skills, and dig down from there.
2. Use your network, which includes things like teammates’ parents.
3. Don’t close an option or opportunity off until you’ve fully explored it. See it through—you never know.

As far as what he wishes he’d done differently, while he’s happy now he does wish he had prioritized his college studies a bit more. He has clarity now that he didn’t have then.

Dwight learned as much as he could along the way, and he has learned a lot. But he’s humble, so talking about what makes him special is clearly uncomfortable for him. But we got him to identify for us what he thinks makes him elite, what makes him a sales pro—and it comes from a) being able to relate to people on a personal level, no matter what role he or they are in, and b) having process and meaning behind his actions.

This points to something important—the power of reflection.  You might feel like you always should be moving, hunting, and making a deal. But stop and take time to reflect. If you’re honest with yourself, self-reflection might be the highest form of learning you can undertake.

Tune in to the podcast to hear details on all of this and more, including how to sell yourself, how to build strong relationships with the AEs you work with, leading a team, and how asking questions might help you find a mentor without even trying. There’s something special that comes through in how Dwight speaks and the words he chooses.