Feature Spotlight #38 - Cheryl Cowherd

A Woman of Grit, Grace, and Good Humor in Title Insurance.

At Her.Collective, we’re always on the lookout for women who are shaping, supporting, and elevating the title insurance industry. This week, we’re proud to feature a powerhouse whose presence has influenced nearly every corner of our profession—from local agencies to national conversations. Meet Cheryl Cowherd, Senior Underwriting Counsel at WFG National Title Insurance Company, based in Kansas City, Missouri.

With a career that spans almost four decades, Cheryl’s story is more than a career path—it’s a testament to endurance, curiosity, and community.

A Serendipitous Start with a Typewriter.

“I needed a job,” Cheryl says with refreshing honesty. That simple statement is how so many great careers begin—and hers was no different.

While in college, a neighbor who worked at Chicago Title helped Cheryl land an interview with a local agent in St. Louis. When asked if she could type, she said, “Sure (sort of),” and soon she was pounding out commitments on an IBM Selectric typewriter—still her favorite machine to this day. It was in those early moments, balancing school and commercial real estate work, that she got her first taste of the title world.

Even after law school, Cheryl found herself drawn back into the business. “I did once or twice, briefly, try something other than title,” she laughs, “but I always came back. Once you're a fit in this industry, it's hard to get out.” What kept her coming back? The constant opportunity to learn. “It’s one of the only careers I know of where you can continually learn new things—which I love.”

From Midwest Roots to National Reach.

Today, Cheryl serves as Senior Underwriting Counsel for WFG, covering both the Midwest and National Agency. From her base in Kansas City, she supports agents across a wide territory with guidance rooted in experience and empathy.

Her role is part legal strategist, part problem solver, and part mentor—and it suits her perfectly. “I just really like what I do and who I do it with,” she says. “I can’t imagine doing anything else.”

The Women Who Paved the Way.

When asked about mentorship, Cheryl is quick to credit other strong women who helped shape her path.

Early in her career at Chicago Title, she worked with underwriter Kathy Thompson, whose mentorship was both impactful and lasting. Through her involvement with ALTA, Cheryl found another guiding light in Nancy Landmark, who remains a source of inspiration today.

“I can’t narrow it to just one,” Cheryl explains. “There have been many women who’ve mentored me and modeled leadership in meaningful ways.”

Cracking the C-Suite Ceiling.

Despite the progress made, Cheryl is candid about the hurdles women still face in the industry. “One of the biggest challenges is moving from the front lines into management—and more importantly, from middle management to upper management. The C-Suite still lacks female representation, especially in larger companies.”

That’s why she believes so strongly in mentorship and visibility—being a leader who encourages and lifts others as she climbs.

Her message to the next generation is clear: “If you like it, stick with it. This is a great industry for women, and it’s getting better every day. There are so many opportunities—and you don’t need an advanced degree to be successful.”

Finding Strength in Simplicity.

When asked about the “why” behind her enduring drive, Cheryl doesn’t hesitate. “I just really like it,” she says. “I find fulfillment in the work itself—and in working with great people.” Her self-confidence isn’t rooted in ego, but in experience and joy. And her resilience? That’s built from showing up for her people, every day. “I guess I have grit—I just don’t think of it that way. I want to be there for my team and my people. That’s what keeps me going.”

Books, Podcasts, and Perspective.

Cheryl’s bookshelf isn’t stacked with business bestsellers. “I’m not a big self-help or business book person,” she says. “When I read, it’s usually what I call ‘brain candy.’”

But one book that did leave an impression was Sheryl Sandberg’s Lean In. “It had a huge impact. I think I’ll reread it—it’s been a while.” She also loved Scott Mann’s The Pineapple Express, a moving account of human compassion, teamwork, and courage during the Afghanistan evacuation.

Her podcast taste reflects her balance of curiosity and escape—from true crime and Dateline episodes to the Calm Down podcast with Erin Andrews and Charissa Thompson. “They’re two women at the top of a male-dominated field, and I love their insights and humor.”

Facing the Tough Stuff.

As a woman in leadership, Cheryl has had to navigate difficult personalities. Her advice? “If possible, deal with them head-on. If you’re not comfortable doing that, talk to a mentor or friend. But in my experience, direct engagement is effective—and teaches you something about yourself.”

She also champions the importance of community over competition. “I’m a big believer in building each other up. Nothing is gained by tearing someone down, even if they’re a competitor.”

Behind the Title: Her Village, Her Life.

Cheryl’s strength isn’t just professional—it’s deeply personal. Her husband, Brian, now retired, is her sounding board, her biggest fan, and often her plus-one and travel buddy. “He has the unique ability—for someone not in the business—to really understand our industry.”

She also cherishes her two stepchildren and eight grandchildren, who keep her world joyful and lively. Her extended family, including a brother and beloved nieces in St. Louis, and a tight-knit group of strong female friends, round out her “village.” “They’ve been there through good and bad times. I couldn’t imagine who I’d be without them.”

A Little Rock and Roll, a Lot of Realness.

Want to know something fun about Cheryl? Her first concert was Shaun Cassidy—a delightful throwback that she shares with a laugh. And her musical tastes? “All over the place,” she admits. From 80s new wave legends like The Cure and The Clash to modern voices like Kacey Musgraves, Billie Eilish, and Pink, Cheryl’s playlists reflect a woman who appreciates both edge and emotion.

Philosophy and Legacy.

Cheryl’s guiding principle is grounded in humility: “Work well with and help others. And never take yourself—or your work—too seriously. We’re not performing heart surgery.”

And when it comes to legacy, she’s not chasing titles or accolades. What matters most? “That I was a good co-worker, a good associate—and that I helped the next generation of women succeed in this industry.”

Final Words for Her.Collective.

Before we wrapped up our conversation, Cheryl left us with this:

 “Support and appreciate each other. Keep your sense of humor. And don’t take yourself too seriously.”

 Thank you, Cheryl Cowherd, for showing us that success in this industry isn’t just about knowledge—it’s about kindness, clarity, and showing up every day with your whole self. You are, without a doubt, a true Warrior within Her. the title collective.

**Connect with Cheryl here: CCowherd@wfgtitle.com I LinkedIn I Instagram