Bound & Determined℠ with Meg McKeen

In this special live experience, host Meg McKeen welcomes consultant and industry icon Deb Smallwood to the podcast, where Deb shares more about her own leadership journey, and how she's supporting women navigating their own leadership today through her SELFPOWERMENT framework. If, out of frustration or hope or despair you've ever asked yourself the question "Why Not Me?" this conversation is for you.

Deb Smallwood is a trailblazing executive and visionary leader on a mission to empower women to become SelfPowered—to embrace their authentic human-being, unlock their inner powers, and thrive in the business world.

With a distinguished career in insurance and technology, including transformative leadership roles at Liberty Mutual, KPMG, TowerGroup, ICW Group, and as Founder/CEO of Strategy Meets Action (SMA), Deb has consistently broken barriers and redefined what’s possible for women in the insurance and tech industries.

After successfully leading SMA through its growth and ultimate sale, Deb turned her focus to her true passion: empowering women to rise above all barriers and become SelfPowered. She founded SelfPowerment, creating a platform centered around her upcoming SelfPowerment book with its formal framework, complemented by mastermind workshops, research studies, and a self-assessment tool—all designed to provide actionable strategies for high-performing women in their personal and professional development, with or without corporate sponsorship.

As a teacher and advocate of SelfPowerment, Deb continues to give back to the business world as a motivational keynote speaker, mentor to rising women executives, and advisor to women-led tech startups.

Deb inspires women to embrace their freedom to thrive authentically, confidently, and intentionally in the business and tech world, while championing a future generation of SelfPowered Women!

• Connect with Deb on LinkedIn
• Learn more about SELFPOWERMENT - and take the self-assessment while you're there!
• Stay in the know as future plans for the next Bound & Determined℠ retreats take shape here
• Have a question for Meg? You can send that to her here.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

In this special crossover experience, Bound & Determined℠ host Meg McKeen and Megan Bell of InsHER, come together for an open, honest conversation about purpose, community, and the power of sharing women's stories. With deep respect for one another’s work, we reflect on what it means to create space for women in the insurance industry, why collaboration matters more than ever, and how podcasting has transformed the way they show up as leaders, listeners, and women.

Megan Bell leads marketing, communications, and customer experience at Falvey Insurance Group, bringing over eight years of industry expertise and a dynamic background in consumer-packaged goods. She is the creator of Women at the Helm and InsHER, both award-nominated initiatives amplifying women’s voices in insurance. A 2025 RISE LEAD Award finalist and recipient of the 2024 ACORD Women’s Insurance Advancement Award, Megan is a recognized industry leader committed to equity, mentorship, and inclusion. She serves on multiple boards and committees, including IMCA, IICF, and RISE, and holds a B.A. in English Communications and Spanish from Emmanuel College.

• Connect with Megan on LinkedIn
• Listen to InsHER on your favorite listening platform here
• InsHER was recognized by Insurance Insiders Honors 2025 with two awards: Women in Insurance and the Progress Award. Learn more about these honors here.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Skylar Romines joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance in Irvine, California, on the Bound & Determined℠ Live in 2025 tour. Skylar reflects on the uncertainty, growth, and knowing that started with the choice she made to redefine her most essential relationships - with work and career, with those closest to her, and with herself. Thanks for being with me in Irvine, Skylar!

Skylar is the founder and owner of ATW Advisors, an insurance consulting firm specializing in working with commercial real estate owners and developers. Acting as an owner’s rep, ATW guides clients through the risk management and insurance procurement process to ensure optimal coverage and cost efficiency. Prior to launching ATW, Skylar spent 17 years as an insurance broker, gaining deep expertise in the industry. She is also the author of So She Did: Stories, Stats & Strategies to Help Women Win; a book that explores the experiences of and aims to give guidance to women in male dominated industries.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

• Connect with Skylar on LinkedIn
• Learn more about the ways Sklyar can support your business through ATW Advisors
• Grab your copy of So She Did: Stories, Stats & Strategies to Help Women Win
• This gathering was hosted at Hera Hub Irvine in Irvine, California, a flexible work and meeting space created with women in mind.
• The Bound & Determined℠ Live in 2025 tour has ended. If you'd like to collaborate with Meg to plan a gathering for women in insurance in your community, message Meg here.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Jenn Walsh joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance in Palo Alto, California, on the Bound & Determined℠ Live in 2025 tour. Jenn reflects on her relationship with ambiguity and the earliest days in her career in employee benefits - and the ways she's showing up now, as a business owner and advocate, as well as a mentor - and a mom. Thanks for being with me in San Francisco, Jenn!

Jenn Walsh is an insurance industry enthusiast who wants people to thrive at all phases of their Sales and Client Service careers. Over the last 35 years, she has developed her expertise within insurance carriers, a full-service brokerage firm, and by holding several leadership roles in national industry associations. She founded GenuineShift in 2018, and its Client Service Academy builds client service teams to help insurance brokers and carriers grow. She lives in San Francisco with her husband and her 39th foster puppy (#fosterfail), Lolo.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

• Connect with Jenn on LinkedIn
• Learn more about the ways Jenn can support sales and client services professionals through GenuineShift
• Listen to Jenn's first appearance on Bound & Determined here
• This gathering was hosted in The Tea Room at the Elizabeth F. Gamble Gardens in Palo Alto, California. Can't recommend working with David and the Gamble Gardens team highly enough.
• The Bound & Determined℠ Live in 2025 tour has ended. If you'd like to collaborate with Meg to plan a gathering for women in insurance in your community, message Meg here.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Tracey Heeter Allen joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance in Portland, Oregon, on the Bound & Determined℠ Live in 2025 tour. Tracey reflects on her decision to pivot - in her life and career - when, after processing the way she experienced the pandemic, as well as a health challenge, and a reprioritization of her core values overall, she started the consultancy that she works in today. Thanks for being with me in Portland, Tracey!

After a 30+ year career in the employee benefits field, Tracey made a career pivot to focus on supporting the employee benefits industry as an entrepreneur. When you hire Tracey, you’ll find she’s an empathetic and intuitive partner. Passionate about the customer experience and work-life integration, Tracey brings sage guidance and support to individuals, teams, and employers. In her spare time, Tracey spends time with her teen, her pup Maddy, and her two cats, Bruno and Pink.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

• Connect with Tracey on LinkedIn
• Learn more about the ways Tracey can support you through The Pivot Project
• This gathering was hosted in the sweet, urban plant shop, Dennis' 7 Dees, located in Portland's Bridgeport Village
• The Bound & Determined℠ Live in 2025 tour has ended. If you'd like to collaborate with Meg to plan a gathering for women in insurance in your community, message Meg here.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Elisha Cavanaugh joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance in Seattle on the Bound & Determined℠ Live in 2025 tour. Elisha reflects on her journey into insurance agency ownership - and as an empathetic leader - a quality that is very much in demand today. We chat about the inverse relationship between our desire to take risks and our age, the reasons we hesitate to ask for help, and the glorification of overwork that is rampant in our industry. Thanks for being with me in Seattle, Elisha!

Elisha Cavanaugh is the owner of Sound Pacific Insurance, an independent agency in Tacoma, Washington, specializing in personal lines. With over two decades in the industry, Elisha started as a teen answering phones and eventually launched her own agency in 2012. In 2024, Sound Pacific Insurance was honored as the Rough Notes Cover Agency of the Year—a reflection of Elisha’s commitment to doing business the right way and building lasting client relationships. She’s an active voice in the industry, serving on multiple carrier councils and mentoring other women in insurance. Elisha leads with grit, heart, and humor, balancing her professional drive with a deep commitment to her family and community.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

• Connect with Elisha on LinkedIn
• This gathering was hosted in the beautiful offices of Safeco Insurance in downtown Seattle
• The Bound & Determined℠ Live in 2025 tour has ended. If you'd like to collaborate with Meg to plan a gathering for women in insurance in your community, message Meg here.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Kay Martin joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance in Missoula, Montana on the Bound & Determined℠ Live in 2025 tour. Kay reflects on burnout - and the private struggle many claims professionals are experiencing today - as well as her experience leading an intergenerational team today. We chat about feeling pigeon-holed in our area of expertise and share more about learning to trust your gut. Thanks for being with me in Montana, Kay!

An expert in carrier claims processes, Kay joined HUB International as the Workers’ Compensation Claims Manager in May of 2016. Kay coordinates interactions between employers and carriers, including claim reviews, loss run reviews, reserve reviews and return to work assistance, and works with HUB‘s producers and clients to customize claims programs, tailored to their unique business needs.

Prior to joining HUB International, Kay worked as a claims adjuster handling workers’ compensation claims in MT, AZ, CO, ID, NE, NV, OR, SD, TX, UT, and WY. Kay’s career includes experience with Liberty Mutual and AmTrust North America.

Kay holds a Montana Adjuster License, a Montana Workers’ Compensation Claims Examiner Designation, an Idaho Independent Adjuster License, a Certified Idaho Workers’ Compensation Specialist Designation, and a Wyoming Adjuster License. She has also earned an Associate in Claims designation from the nationally recognized industry leader, The Institutes.

Kay has embraced the Missoula lifestyle since arriving in 1998. She loves the community and the outdoors. She enjoys volunteering, running, hiking, camping, golfing and reading.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

• Connect with Kay on LinkedIn
• This gathering was hosted in the Lounge at The Roxy, a non-profit theater in Missoula, Montana
• The Bound & Determined℠ Live in 2025 tour has ended. If you'd like to work with Meg to plan a gathering for women in insurance in your community, message Meg here.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Michelle Raue joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance in Nashville on the Bound & Determined℠ Live in 2025 tour. Michelle reflects on aging - and ageism - and the wisdom she's gleaned throughout her career - and life. Michelle is witty and she is honest - and together we share about our mutual distaste for networking - at least in the traditional sense - and unite in our support for more mental health support in the workplace. Thanks for sharing this experience with us in Nashville, Michelle!

Michelle Raue is a seasoned leader with over 30 years in the property and casualty insurance industry. Throughout her experience, currently as EVP, Chief Claims and Transformation Officer at Preferred Mutual Insurance Company, and previously with Lyft and State Auto, Michelle has been known for driving innovation, operational excellence, and transformative change.

Michelle holds a BS in Finance from the University of South Alabama and has completed advanced AI courses at MIT Sloan. She is actively shaping AI regulations in insurance through NAMIC and is passionate about talent development, serving as Chair of the STEM Connector’s Women in Insurance Catalyst Committee and an Advisory Board Member for RISE Professionals. In 2024, she was named RISE Professionals Mentor of the Year.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

Bound & Determined℠ Live in Nashville is presented by Market Retrievers. Market Retrievers helps insurance professionals through digital marketing, social media, and content strategy. Learn more at marketretrievers.com.

• Connect with Michelle Raue on LinkedIn
• This gathering was hosted in the beautiful and luxe coworking space, The Sapphire Suite, in Franklin, Tennessee.
• The Bound & Determined℠ Live in 2025 tour has ended. If you'd like to work with Meg to plan a gathering for women in insurance in your community, message Meg here.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Tinsley English joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance during the Atlanta stop on the Bound & Determined℠ Live in 2025 tour. Tinsley reflects on the notions of resilience - and reinvention - as we align our career with our purpose – and how to identify your purpose if you’re not sure, and we chat more about journey many women are on today as they navigate menopause. As only she can do, Tinsley provides actionable wisdom with honesty and heart throughout. Thanks for joining me in Atlanta, Tinsley!

Tinsley English is a best-selling author, operations leader, female development coach, keynote speaker, and podcast host with over two decades of commercial insurance expertise spanning regional agencies, national firms, and carriers. As the founder of The Three G Consulting Group LLC, she transforms women leaders through her proprietary G-Force Code System. Her signature 24-Carat Leader program empowers professionals to amplify their visibility, accelerate career advancement, and master strategic decision-making. A dynamic speaker, Tinsley champions male allyship, prepares college students for professional excellence through her Next Step Navigator Program, and inspires audiences through her podcast, where she shares insights on leadership, resilience, and career growth.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

• Connect with Tinsley English on LinkedIn
• Grab your copy of GRIT, GROWTH AND GUMPTION: Three Keys to Lead Yourself and Others with Confidence here
• Learn more about the ways Tinsley can support you or your organization here
• This gathering was hosted in the beautiful Poe & Company Bookstore in Milton, Georgia
• Join Meg for one of the remaining live podcast recording events she'll be hosting in 2025. Learn more about Bound & Determined℠ Live.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!

Diane Wagner joins host Meg McKeen for a conversation recorded during an intimate gathering of women in insurance during the Charlotte stop on the Bound & Determined℠ Live in 2025 tour. Diane reflects on her earliest days in insurance, the urgency she felt to find success - and the lengths she'd go to find it - and what that success looks like for her today. We talk about money - it's not easy, but it's necessary as women plan for their own financial futures. Thank you for joining me in Charlotte, Diane!

Diane Wagner is the VP of Strategic Planning and Education for FirstChoice a MarshBerry Co., Insurance Journal’s number one agency partnership for two consecutive years. Diane has 45 years of insurance experience, 20 years on the carrier side and the last 25 years starting two top insurance networks from scratch.

Diane sits on the board of Invest, a nonprofit arm of the Independent Insurance Agents Association. Invest educates students on insurance, financial services and risk management while encouraging them to pursue insurance careers. Introducing insurance as a career to young people and helping agencies build effective talent pipelines is Diane’s passion project.

Diane travels extensively, enjoys concerts, golf, and spending time with her life partner, friends, and her two grown children.

Bound & Determined℠ Live in 2025 is presented by RISE: Empowering Women in Insurance™ by Liberty Mutual, a program dedicated to bringing women in insurance together through connection, education, recognition, insights and allyship. Join us in the RISE LinkedIn Community today.

• Connect with Diane Wagner on LinkedIn
• Learn more about Invest, a program through the Independent Insurance Agents & Brokers of America, supporting and encouraging students as they consider a career in the insurance industry.
• Join Meg for one of the remaining eight live podcast recording events she'll be hosting in 2025. Learn more about Bound & Determined℠ Live.
• Have a question for Meg? Submit it here and she may answer it on a future episode.

To learn more about this podcast, and the work Meg McKeen does to support insurance professionals, visit Adjunct Advisors. To receive To Taking the Risk, the monthly newsletter Meg curates, including updates on her #digitalnomad adventures, subscribe here.

Love the podcast? To show your support, consider leaving a positive review here, sharing this episode with a friend, or making a financial contribution here. Thank you for listening!