Risk Takers and Trailblazers Women in Insurance

How do you build, scale, and lead three separate "unicorn" tech companies—all while maintaining your mental health and building a world-class culture? In this episode of Risk Takers & Trailblazers, we sit down with Kelly Schmitt, CEO of Headversity and former leader at Benevity, Solium Capital, and SMART Technologies.

Kelly breaks down the unfiltered truth about scaling global companies, the crucial difference between mentors and sponsors for women in leadership, and why psychological safety is NOT about "being nice"—it’s about high accountability and radical candor.

🔥 IN THIS EPISODE, WE COVER:
• The common threads behind scaling 3 Calgary tech unicorns
• How to build organizational resilience & normalise failure
• Mentors vs. Sponsors: Why women need someone to "kick down doors"
• The reality of burnout and taking a full year off in Barcelona
• What psychological safety actually means (and why you must fire "high-performing jerks")
• Why culture beats strategy every single time

💡 BOOK RECOMMENDED BY KELLY: "I Never Thought of It That Way" by Mónica Guzmán---

📌 SUBSCRIBE & FOLLOW
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🎙️ Listen to the Risk Takers and Trailblazers Podcast on your favourite platform:
https://podcasts.apple.com/us/podcast/risk-takers-and-trailblazers-women-in-insurance/id1896943558

https://open.spotify.com/show/033B5z3noL3FWNMiwhqyGP/

CONNECT WITH US:
• LinkedIn: https://www.linkedin.com/company/risk-takers-and-trailblazers-podcast
• Kelly Schmitt LinkedIn: https://ca.linkedin.com/in/kellyschmitt


#WomenInInsurance #Insurtech #leadership #StartupScaling #WomenInTech #PsychologicalSafety #RiskTakersAndTrailblazersS.4

What happens when everything looks successful on the outside… but no longer feels aligned on the inside?

In this episode of Risk Takers & Trailblazers, hosts Diane Horsfield and Tanya Coburn sit down with executive coach and insurance leader Jen Weigel for an honest conversation about leadership, identity, resilience, and what it means to evolve without losing yourself.

From growing up in small-town Alberta to building a career in insurance, pursuing music professionally, and ultimately becoming an executive coach, Jen shares the experiences that reshaped how she leads and how she helps others grow.

Together, they explore:

✨ The emotional weight leaders carry behind the scenes
✨ Why vulnerability builds stronger teams
✨ The difference between mentoring and executive coaching
✨ Psychological safety and creating trust at work
✨ Finding your authentic leadership style
✨ Why success doesn’t always equal alignment
✨ How to stop performing and start showing up as yourself

One idea from this episode that stayed with us:

“Better is possible.”

If you’ve ever felt pressure to have all the answers, wondered who you are outside of achievement, or wanted to lead in a more human way — this conversation is for you.

Follow Jen Weigel on LinkedIn:   / jenweigel  
Follow Risk Takers on LinkedIn:   / risk-takers-and-trailblazers-podcast  

🎙️ Hosts: Diane Horsfield & Tanya Coburn
🎧 Guest: Jen Weigel
🎬 Production Engineer: Jessica Kohinski

Subscribe for more conversations with the women shaping the future of insurance, leadership, and business.

In this episode of Risk-Takers & Trailblazers, we are joined by FLORA Fertility co-founders Dr. Christy Lane and Laura McDonald to discuss how they're transforming fertility coverage and creating a new category in insurance.

Fertility challenges affect millions of individuals and families, yet access to affordable coverage remains limited. Kristi and Laura share their personal journeys, the inspiration behind FLORA, and why they believe fertility protection should be proactive—not reactive.

In this episode we cover:

• Why fertility has become one of the largest future financial expenses for young adults
• The gaps that currently exist in fertility coverage across North America
• How FLORA's innovative insurance model helps individuals plan ahead
• The role employers can play in supporting fertility benefits
• Why community, education, and awareness are critical to women's health
• What it's like building a female-led startup in the insurance industry
• How FLORA successfully raised a $5M USD funding round as a women-founded company

Whether you're planning for the future, navigating fertility challenges, interested in women's health innovation, or building a business of your own, this episode offers valuable insights on leadership, resilience, and creating meaningful change.

Connect with FLORA and learn more about their mission to make fertility protection accessible for everyone. www.heyflora.com

Follow Flora on LinkedIn:   / heyflora  

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Follow us on Instagram: / risktakers_trailblazers

Follow Jen Pugsley: / jennifer-pugsley-turcsanyi-4ba73234

Follow Helen Riquinha: / helen-riquinha-26b00438

Follow Diane Jones: / dianejonestrufla

Follow Tanya Coburn: / tanyacoburn