Deb Smallwood discusses her mission to empower women in insurance and beyond

Women comprise about 60% of the insurance workforce, yet hold only 23% of executive positions at carriers. In technology leadership, the gap is even wider — with women occupying just 11% of CIO roles. For industry veteran Deb Smallwood, these aren’t just statistics. They are a spotlight on today’s reality — and a call to action.

After 46 years in the insurance industry — from starting as a COBOL programmer trainee to becoming a CIO, Big 4 Consulting Partner, and Founder/CEO of Strategy Meets Action (acquired by ReSource Pro in Jan. 2021 ) — Smallwood has shifted her focus. The mantra that propelled her own career, “Why not me?”, has now expanded into a collective vision: “Why not us?” — and a drive to be the change she wants to see for women in business.

“This is why I launched the book project called SelfPowerment,” she explains. “SelfPowerment is about guiding high-achieving women to believe in themselves, tap into their inner power, and step boldly into the career and life they desire, dream about, and deserve.”

A career built on possibility

Smallwood’s own career proves what’s possible when, as she says, “curiosity and courage meet opportunity.” Over four decades, she held more than 20 roles, breaking ground as a CIO, CEO, and Partner at a time when women in leadership were rare.

“I always looked up and out and saw infinite possibilities,” she reflects. “That mindset propelled me forward even when the path wasn’t clear.”

For her, the vastness, financial stability, and people of the insurance industry remain its greatest strengths. “This is an industry where you can pivot, stretch forward, and advance — with the support of leaders across the industry,” she says. “There are incredible opportunities for those willing to see them, and with confidence, reach for them.”

Research that revealed truth

When Smallwood set out to write her book, she drew on her research expertise honed from years as Founder/CEO of Strategy Meets Action, a research and advisory firm. She conducted an in-depth qualitative study of women leaders in insurance and beyond — interviewing over 50 senior women and 10 male executives, capturing more than 300 hours of conversations and analysis.

What emerged was not just data, but a chorus of lived experiences and clarity about why there is a woman leadership gap.

Common Themes:

• It is Still Significantly Difficult for Women in Business
  Not just in insurance — women described how they often feel they must work harder, take on “big ugly strategic” projects,  afraid to say no, and continuously prove themselves to advance.  Gender bias and discrimination are still real, at least in their minds and experiences.
• Roadblocks and Resilience
  Nearly every leader described a defining setback — a layoff, a missed promotion, or being sidelined. The greater challenge wasn’t the event itself but the self-doubt that followed. Women tended to carry that doubt longer and internalize it more than men.
• The Confidence Gap
  Even top-performing women hesitated to pursue leadership roles, questioning their readiness. As one CIO admitted: “I was asked to apply for the senior role, and I almost didn’t  because I didn’t think I was ready.” That’s typically not a response heard from men.
• Operational vs. Strategic Leadership
  Women often excelled in execution — running major programs and operations— learning from the details forward.  Yet they struggle as they advance into new areas of leadership positions – grappling to find the right strategic voice from the top down of the why and what from the details of operational defining problems and the how’s.  “Executive presence and having a confident strategic voice are key — it’s a big shift for many,” Smallwood  notes.
• Intentional Connections
  Mentorship, sponsorship, and strong networks consistently proved to be game-changers. Yet many women, if they find the time to network for themselves, sought emotional support and peer groups over career advocacy, while men networked more strategically for advancement — allowing men to pivot faster and easier.
• Complex Choices
  For some, the C-suite was never the goal. “I’ve met brilliant, high-achieving women who simply didn’t want to ‘play there’, ” Smallwood observed. “Opting out is part of the story too.” This contributes to the smaller female executive pipeline — an area that can and must change.

From Book to Movement

What began as a book project soon evolved into something much larger.

“I thought I was just writing a book and would be done in six months,” Smallwood laughs. “Two and a half years later, I have a SelfPowerment platform — with a fully edited 45,000-word manuscript ready to be published, various frameworks, tools and workbooks, plus the formal research study,  and the beginnings of a movement.”

Through the many conversations, interviews, and interactions with high-achieving women, she discovered something powerful: SelfPowerment guides women to catch and release the noise of self-doubt in their heads, reclaim their inner power, and step into their careers — with confidence and intent.

“There’s something profound about hearing another woman say, ‘I thought it was just me,’” Smallwood notes. “When these women realize they’re not alone, it dissolves self-doubt and builds resilience.”

Why Not Us?

For Smallwood, the shift from “Why Not Me?” to “Why Not Us?” is about more than closing gaps in statistics. It’s about transforming how women see themselves, how they lead, and how they support one another.

“SelfPowerment is about making the InnerShift from proving to being. From self-doubt to clarity. From silence to a strong voice. When women rise with presence and intent, the whole industry rises with them.”

The SelfPowerment platform is built on a foundation of research, experience, and passion. With her forthcoming book, “SelfPowerment: The Inner Shift for High-Performing Women Who Want More Than Success,” Smallwood is focused on expanding her programs and  continuing to grow the community she’s built.

“I don’t have all the answers,” she admits. “But I do know this: when women acknowledge their power, awaken their wisdom, accept what is, and align with their truth — they are unstoppable. And when we do this together, we move from ‘Why Not Me?’ to ‘Why Not Us?’”