The Art of Storytelling: Leadership Lessons with Will Womble

Will Womble
Will Womble

What happens when you get a storyteller unsure of how to tell their own story? A paradox—oh, and a pretty darn good read. I recently sat down with Will Womble to share in a discussion, and while there were no expectations or pressures, an underlying need to find the "it factor" was encompassing. Like an archaeologist excavating a fossil, I searched, but little did I realize a story is not simply found; it is heard. And the more I listened, the more Womble's story materialized.

"That's what I believe all of us are. We're storytellers," he says. While he may have been hesitant at first to "dip a toe in the water," Womble's leadership story was revealed, and the lines of his script flowed richly.

But first, an introduction. Will Womble is what you'd call a man who wears many hats, with experience as an actor, lawyer, and currently, CEO, but even within his company Umbrage, Womble's roles include go-to-market execution, branding, marketing, recruitment, and contract negotiation. When the right and left brain work synonymously, what are you left with? In Womble's case, too many hats and his company Umbrage, a digital product studio specializing in crafting custom software solutions to solve companies' challenges.

"At our core, Umbrage delivers AI-empowered software, but more than that, we're cultivating culture within our client's organizations," the website states.

"Whether it's our team that is designing or developing software, they're telling some sort of story," he shares, "We don't have a product that I can pull out of my pocket and tell people it's the solution to all their problems that we don't really know. we actually have to listen. In real-time, in a room, and understand what they're trying to do to figure out how to solve a particular product to their problem," aka, create a compelling story.

After five years of growth with Umbrage, growing from 6 employees to 200 next year, Womble is ready to share his story, which is also Umbrage's. Think of it as a debrand, if you will.

From acting on sets such as Pearl Harbor to graduating law school and (6 years later) becoming a DA prosecuting cases to joining a startup tech company, Chaotic Moon, the dots eventually connected.

Once they did, Womble discovered his bailiwick in the startup world and ran, leaving a trail of anecdotes along the way. Here's what I gleaned from his leadership story:

Part 1 – Voir Dire

"A pitch room and a boardroom are very similar to a courtroom," Womble says. The commonality? The art of persuasion, or storytelling, is a skill he honed at the DA's office. "I enjoy the goal setting and analytical necessities to accomplish things, but I love the creativity with which one can go about accomplishing that, especially in a courtroom."

"If I painted the entire picture and just told the jury everything they needed to get to, it didn't always work," he explains. Giving up that control, so to speak, was much more effective, a tactic that also translated into business. If there's one thing you take from Womble, it's learning to talk to people, not at them, as storytelling in business boils down to building trust and connection—a foundational aspect of Umbrage.

"That's the difference between being talked at and talked to, and that is a skill set... I'm trying to educate people on who it is we are, what it is we do, and how it is we do it. I'm trying to get them to like me, much like I was trying to do during my voir dires."

Part 2 – Company Culture

"I think culture is something you can't curate in a petri dish. You can only give it water and sunlight and hope that it sprouts, but you cannot manufacture it," says Womble, with vulnerability going hand in hand. "I don't care how smart or talented an individual is, you can't build a multimillion-dollar company that exits by yourself. You need people, and you need to be able to be vulnerable with those people to get through the inevitable tough times."

Creating a strong culture within any business is an essential part of building and maintaining success, and given Umbrage's year-over-year growth in four out of five years, it has been a proven method for Womble and his team.

"It's been interesting to see the human spirit bond together and galvanize, even though we don't always see eye to eye, and even though not everyone stays here forever," he continues. Despite being bought by Bain & Company last year-one of the top three strategy firms in the world—this sense of family unity within the company has remained. A credit to the autonomy Womble curated and remained steadfast in upholding.

"I'm still the CEO of the company. We're still running independently, even though we're wholly owned by Bain ... I always tell prospective employees, 'Hey, you'll never see it in a paycheck, and you'll never be able to deposit, but you'll know when it's not there. And that's autonomy.'"

Subscribing to Ted Lasso and Michael Scott's theory of life to "be cheesy in everything," he set the precedent for his company's culture even before inception. As a storyteller, there is of course meaning behind Umbrage's logo. "There's a reason our helmet is our logo ... My line to the team is when you put the helmet on, everybody looks the same. How do you build a company that still has the same six people originally hired from day one to day two? I believe it has to do with the ethos at which you align and how you're going to go and do things together, no matter the strategies."

Part 3 – Being OK in the Shade

"Umbrage comes from the Latin root word umbrāticus, which means shade. This is very antithetical to what I wanted to build as a company," says Womble. "We'll build your product, we'll build your team, and over time, build ourselves out of a job. Because we'll help hire, we'll help interview, we'll train and embed your folks with us. We'll teach you to fish so that you can fish for yourselves once we get out."

"We have found a niche in solving problems for internal users," he continues, which includes internal healthcare workers, field workers, plant workers, and so on. Drawing an analogy between Umbrage and the CIA, his team infiltrates, trains, teaches, and empowers other companies, and then gets out successfully, leaving it in greater standing, with others thinking the company achieved it on their own—a cloak-and-dagger method.

"We built this entire company off of relationships and people giving us a chance," Womble concludes. And now, "I'm putting my story out there to hopefully help others."

As this story comes to a close, the script for Womble's next pursuit is already unfolding.

To learn more about Will Womble, visit his LinkedIn page and check out Umbrage's website here. Everyone has a story to tell—Umbrage can help you share it.

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