INSIGHT

Why People Stay: Clay Wolff on Ten Years of Leadership & Learning

By Clayton Wolff

Clay Wolff never set out to build a career in sales. He set out to challenge himself, to learn, to listen, and to help people solve problems. Ten years later, he’s still learning the fretboard.

When We Made the Intro to Another Firm

It was around 2021 or 2022. Kenway was in the midst of rolling out its targeting strategy, focusing on larger enterprise prospects. They identified a strong relationship at a major account, got introduced, and had a fantastic conversation.

"That conversation continued to morph in terms of the need, the problems, the requirements," Clay recalls. "In the end, it turned out that what they needed was not the skill set that we were bringing to the table."

Kenway believed they could do it—they’re smart people. But they didn’t have direct experience.

"If we weren't a principles-driven organization, if we didn't have our guiding principles to anchor us, I could see a lot of firms starting those engagements, charging ahead, and learning as they go - often at the client’s expense," Clay says.

Kenway chose the opposite path.

"As soon as we gained consensus internally that this was out of our wheelhouse, we went directly back to the prospect, had that conversation, and said that we would be more than happy to make introductions to other contacts we have in the ecosystem."

And they did—introducing the firm that ultimately got the job.

"We walked away from revenue, but we gained something more valuable," Clay notes. "Trust. And that trust has led to some of our most strategic relationships—clients who return year after year with new challenges because they know our focus and principles never shift."

"Help and Be Helped" as a Framework, Not a Tagline

At Kenway, help and be helped isn’t marketing language—it’s the operating system.

"Traditional sales functions often chase transactions above all else," Clay explains. "But our approach centers on genuine curiosity and an authentic urge to solve problems for those who need and want help."

The difference shows up in subtle but powerful ways. "I've found that when we lead with genuine intent to understand and solve a problem for a prospect or client—even if we end up not being the right fit—it makes a lasting impact. It builds trust and reciprocity, which in turn leads to achieving more of the right outcomes, the right way."

The Question Clients Should Ask

When asked what potential clients should ask consultants but don’t, Clay doesn’t hesitate.

"What will you do when it's not in your best interest to tell us the truth, or when you know it's not what we will want to hear?"

"Too often, conversations with consultants revolve around capabilities, experience, or methodology, but rarely about integrity when those behaviors are tested," he says. "The real differentiator in our profession isn't technical or functional expertise—it's the courage to deliver honest perspectives, even when they challenge the client's assumptions or risk short-term revenue."

That’s where Kenway stands apart. "Being transparent, regardless of the outcome. If we're not the right partner, or if the client isn't prepared to accept the help, we'll say so. Because that's what 'help and be helped' truly looks like."

The "Rising Star" Lesson

Being named a Rising Star by Consulting Magazine was humbling—and instructive.

"It was honestly a bit shocking, given the caliber of talent present both across the consulting industry and within Kenway," he says. "I'm surrounded by people who carry a massive intellectual baton into every discussion they participate in, who were generous with their time when I was a junior consultant, and who remain just as generous today. They passed that baton through their mentorship and encouragement, enabling me to maximize my potential. The Rising Star recognition was as much a reflection of them as it was of me."

The recognition taught him something essential: "Success in consulting isn't about individual accomplishments—it's a reflection of the people you work with, the trust they place in you, and the trust you place in them."

"The most meaningful outcomes in my career haven't come from the pursuit of recognition, but from investing in relationships and watching others grow as a result of the culture we've built together," Clay explains. 

Ten Years In: Still Learning the Fretboard

Clay has been at Kenway for a decade. "Typically, if you work anywhere or do anything for 10 years, you’d expect to have it mastered," he says. "I don't feel that way. The consulting industry is constantly evolving, and I’m surrounded by incredibly sharp people - at Kenway, among our clients, and even our prospects - who continually challenge me to keep learning, improving, and stretching in new ways."

The challenge, he says, is "intoxicating, and at times a bit terrifying. But over these last ten years I have been taught to be patient, to stay curious, and to put myself in uncomfortable positions until they start to feel more familiar."

His guitar journey mirrors his Kenway journey perfectly. "You hand me a guitar, I know how to play it now. You put me in a consulting company, I know how it works now. I didn't always. Both took some time."

But that growth needs the right environment. "You have to have that entrepreneurial spirit. You have to have people around you that are willing to give you their time and their energy to help you get better. Without that, it’s easy to see why consulting can sometimes be viewed as such a tough, even cutthroat, industry."

"Why?" Clay asks. "Because in many firms, there isn't that same investment in each other's growth. But there's a reason why people at Kenway stay. You're surrounded by people who not only inspire you to grow, but they give you their time and their energy so they can actually propel you forward."

Progress Comes from Patience and Practice

Outside of work, Clay lives the same philosophy he practices professionally.

Morning workouts are his secret weapon. "They clear my head and reset me before the chaos of the day begins."

Golf is another hobby that’s been a surprising teacher. "I can’t get enough of it. It’s a challenge that keeps me coming back. The game demands patience, focus, practice, and support from others to perform at your best—much like the work we do every day."

And then there’s home life. "Most nights are filled with my wife, Emily, and I tag-teaming parenting duties - passing off our baby girl to one another to craft a Lego tower, playing backyard sports with our boys, and spinning up bedtime stories about dragons and flying hippos. It's chaotic in the best possible way."

When things finally quiet down, he’ll pick up his guitar. "Not because I'm good at it, but because it's meditative. It reminds me that progress comes from patience and practice, not perfection."

That mindset, he says, is what makes him effective in his role at Kenway. "Before I started here back in 2015, I never set out to build a career in sales, let alone lead Kenway’s Business Development organization. I set out to challenge myself, to learn, to listen, and to help people solve problems. Over time, I realized that's what true business development is: leading with curiosity, leveraging support from the team, helping where you can, and trusting that growth follows from a focus on executing the right means."

Why People Stay

Recently, Clay was on a call with Sarah Welch, Joe Steelman, and another longtime colleague. Everyone had been at Kenway for over 10 years—some substantially more.

"The person we were talking to was like, 'What is going on? You don't run into a lot of phone calls where four individuals, all very different in ages, have all been at the same company for north of 10 years.' It's remarkable."

But it’s not accidental.

"What’s special about Kenway is that the experience doesn’t change, no matter what’s happening with revenue or growth," Clay explains. "That kind of consistency and culture is unique. Whether we’re hitting record numbers or experiencing a tough year, the way we treat and show up for each other every day stays the same."

For Clay, staying at Kenway comes down to something simple but rare: being surrounded by people who are brilliant, hardworking, and genuinely invested in each other's success.

Help and be helped isn't just culture. It’s why people stay.

Help & Be Helped isn’t just a philosophy — it’s how we lead at Kenway. Connect with Clay Wolff on LinkedIn or read more stories of how Kenway brings Help & Be Helped to life on our Insights page.

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