Women make up nearly 60% of the insurance workforce, yet only 23% of carrier executives and just 11% of technology leaders. For Deb Smallwood, these aren’t just statistics. They’re proof that meaningful change in insurance leadership still has far to go.
After 46 years in the industry – from COBOL programmer to CIO, Big Four consulting partner, and Founder/CEO of Strategy Meets Action (acquired by ReSource Pro in 2021) – Smallwood has shifted her focus from personal achievement to collective empowerment.
Her new mission begins with one powerful shift in mindset: from “Why not me?” to “Why not us?”
Turning Experience into Empowerment
Smallwood’s latest initiative, SelfPowerment, is both a book and a movement; a call for women to embrace confidence, clarity, and community in their careers.
“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,” she explains.
Her four-decade journey embodies that philosophy. From her start as a trainee programmer to leading consulting practices and founding a respected research firm, Smallwood’s success was built on curiosity, courage, and possibility.
“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.”
What the Research Revealed
True to her analytical roots, Smallwood approached SelfPowerment as both a researcher and a leader. She interviewed more than 50 senior women and 10 male executives, gathering over 300 hours of conversations to uncover the root causes behind the persistent leadership gap in insurance. The findings revealed familiar — and still stubborn — patterns:
- Persistent barriers: Women continue to feel they must work harder, take on more, and constantly prove their worth.
- The confidence gap: Even high-performing women hesitate to pursue leadership roles, questioning their readiness.
- Operational vs. strategic leadership: Many women excel in execution but struggle to claim a strategic voice at the executive level.
- Networking imbalance: Men network for advancement; women often network for emotional support.
- Complex choices: Some women consciously opt out of the C-suite, further narrowing the leadership pipeline.
“It’s still significantly difficult for women in business,” Smallwood says. “But acknowledging that truth allows us to address it with intent.”
From Research to Movement
What began as a book quickly evolved into a leadership platform, complete with tools, workbooks, and workshops designed to help women quiet self-doubt and step into leadership with authenticity and purpose.
“There’s something powerful about hearing another woman say, ‘I thought it was just me,’” Smallwood notes. “When women realize they’re not alone, it dissolves doubt and builds resilience.”
At its core, SelfPowerment is about making an InnerShift – from proving to being, from hesitation to clarity, and from self-focus to collective growth.
Why Not Us?
Smallwood’s message to women in insurance is simple, and transformative.
“When women acknowledge their power, awaken their wisdom, and align with their truth, they’re unstoppable. And when we do this together,” she says, “we move from ‘Why not me?’ to ‘Why not us?’”
Read the full article and explore more insights on digital transformation and insurance innovation at The Insurance Lead.
