Connected Conversations In Insurance

Ask a room full of high school seniors what they want to do with their lives and you’ll hear a lot of answers. Doctor. Engineer. Designer. Entrepreneur. What you almost certainly won’t hear is: insurance. And that, says Kelly Smith, is exactly the problem. In this episode—our first two-guest conversation of the season—Kelly Smith and Moira Bocrie sit down together to make the case for why insurance is one of the most remarkable career opportunities young women aren’t considering. Kelly brings more than 20 years of industry perspective. Moira brings something equally powerful: she’s living the early-career reality right now.Together they talk about what young women typically imagine when they hear ‘insurance career’—and how far that picture is from the reality. They make the case for the non-college path, the entrepreneurial path, and the financial opportunity that almost nobody talks about loudly enough.This is the season’s most explicitly forward-looking episode before the finale—and the one most likely to change what a young woman believes is possible for herself.

Staying Nimble: Adaptability as Your Greatest Competitive Advantage — Showna Jones

In this episode of Connected Conversations (Canopy Connect podcast, Women in Insurance), host Carrie interviews Showna Jones, who spent over 20 years in insurance—primarily in claims, catastrophe, and compliance—after serving in the U.S. Army as a medic.

Showna shares how an accumulation of corporate experiences and a pivotal conversation with an agency owner led her to launch Timeless Insurance Agency in Hampton Roads, Virginia, then quickly grow by acquiring a retiring colleague’s agency and earning key carrier appointments. She frames adaptability as a deliberate choice to pursue growth before it’s forced, built through stretching yourself, networking, mentorship, and community groups like CPCU and NAIFA. Showna discusses navigating male-dominated environments, redefining success as control and well-being, and encouraging women to get comfortable being uncomfortable and trust that no experience is wasted.

Connect with Showna:

LinkedIn: https://www.linkedin.com/in/showjones/

Phone Number:  757-324-3747

Timeless Insurance Agency: https://timelessinsuranceagency.com/

The Long Game: Career Pacing and Ambition in Insurtech | Brenna JohnsonWhat does sustainable ambition actually look like?In this episode of Connected Conversations: Women in Insurance, Carrie sits down with Brenna Johnson, SVP of Product Management at EZLynx, to explore what it means to build a meaningful career in insurtech without losing yourself along the way.Recently recognized by Big I Magazine as one of the women driving innovation in insurtech, Brenna shares the pivotal moments that shaped her leadership journey—from learning to stop imitating others, to embracing her authentic leadership style, to understanding that slowing down for a season doesn't mean giving up on your ambitions.Whether you're just starting your career, considering a move into insurtech, or navigating your next leadership opportunity, this conversation offers practical advice and encouragement to trust your voice and embrace growth—even when it feels uncomfortable.

Community isn't just a buzzword—it's the thing that can completely change the trajectory of your career. In this episode of Connected Conversations, host Carrie sits down with Ashley Engl, Director of Technology, Learning, and Innovation at Walsh Insurance, chair of Big "I" New York Next Gen, and a Big "I" National YAC representative, to dig into why professional community—especially women-only spaces—matters so much in insurance.Ashley shares her winding path from banking to benefits to agency operations to her current role in insurtech, and opens up about the women's summits, roundtables, and networking spaces that have shaped her career. If you've ever felt like networking is intimidating, or wondered how to find "your people" in the industry, this one's for you.

Connect with Ashley Engl on LinkedIn: https://www.linkedin.com/in/ashleyengl/

In this episode of Connected Conversations, host Carrie (Canopy Connect) talks with Brooke Liu, SVP at MarshBerry and leader of MarshBerry Connect, about the “quiet, creeping” burnout high achievers often hide—what Brooke calls operating in “low power mode.” Drawing from her work with her peers and her own intense travel schedule, Brooke explains that burnout is a capacity issue, not a motivation problem, and shares early warning signs like fatigue and declining sleep quality. They explore why women may carry extra burnout weight through credibility pressures, emotional labor, and difficulty delegating, and why asking for help can protect credibility more than masking struggle. Brooke offers practical strategies—accountability partners, communicating priorities, time-and-energy audits, and rejecting constant work-life balance in favor of seasonal grace—plus organizational ways to spot and reduce burnout through surveys, benchmarks, staffing, process standardization, and technology.

Connect with Brooke:Email:  [email protected]: https://www.linkedin.com/in/brookeacliu/Marshberry LinkedIn: https://www.linkedin.com/company/marshberry/

This season, we have talked about confidence and self-advocacy. And now Dawnyel Smink arrives to ask the harder question: what gets in the way of both?

Dawnyel is the President and CEO of Canyon Lands Insurance and CLI Select Agencies—a network of more than 80 affiliated agency locations across 18 states. She is the co-founder of WIISE, Women In Insurance Sharing Empowerment. She is the author of Don’t Project Your Sh*t on Me! And she has spent more than 15 years building a philosophy of personal ownership that is equal parts framework, fire, and radical honesty.

Her ‘I’ll Own It’ framework is built around a single conviction: that real leadership—and real freedom—comes from doing the hard internal work. Breaking toxic cycles. Owning your choices. Stopping the unconscious habit of putting your unprocessed stuff onto the people around you.

And then she goes somewhere that almost no one in this industry goes.She talks about what women are managing biologically across a career—and doing it mostly in silence. Pregnancy and postpartum. The years of raising teenagers while building a business. Aging parents. Perimenopause. Full menopause. The hormonal, neurological, emotional reality of being a woman whosebody is changing while the world keeps expecting her to perform at full capacity. Dawnyel has lived all of it. She is talking about it openly because she believes the silence costs women more than the conversation ever could.

She wants you to know something. You are not alone. And you are not crazy.

Connect with Dawnyel: Website: https://dawnyelsmink.comDon't Project Your Shit on Me: https://dontprojectyourshitonme.comWIISE: https://wiisewomen.com/home

In this episode of Connected Conversations, host Carrie speaks with Megan Bell, SVP of Marketing at Falvey Insurance Group and creator of the Insure podcast, about self-advocacy, presence, and navigating conflict.

Megan shares her path into insurance from consumer products, her motivation to spotlight women leaders through Insure, and why women often struggle to ask for what they want due to self-consciousness, comparison, and workplace dynamics.

They discuss how male-dominated environments and informal networks can affect visibility, and how conflict can be calm, fact-based, and focused on resolution.

Megan offers practical strategies like preparing, starting tough conversations in writing, finding mentors, building confidence through small steps and communities, and leaders creating open communication channels and recognizing women’s ideas.

Connect with Megan: Linkedin: https://www.linkedin.com/in/megan-bell/InsHER Podcast: https://www.insherpodcast.com/

Building Confidence from the Inside Out — Sharilyn Tanaka

In this Connected Conversations episode launching season four on women in insurance, co-host Carrie Thornbrugh interviews Sharilyn Tanaka, Executive Vice President and Unit Manager for Business and Personal Insurance at Atlas Insurance in Honolulu. Inspired by a YWCA Oahu women’s leadership program, Tanaka explains that confidence can be built and shares five practical strategies: build expertise through education and designations, track successes and impact, act before you feel fully ready, use your voice consistently, and build a supportive “village” including mentors and sponsors who advocate for you when you’re not in the room. She discusses navigating self-doubt—especially as an introvert in male-dominated rooms—by focusing on preparation, speaking up, and accepting imperfection, particularly for working mothers.

Michael Ley on Agency Networks, Tech Stacks, and the HawkSoft Purple Cow | Connected Conversations in Insurance

In this episode of Connected Conversations in Insurance, Ray Huang sits down with Michael Ley, Director of Network Relations at HawkSoft, to talk about what agency networks and aggregators are doing to stand out and deliver real value beyond commission splits.

Michael shares his journey from a family-owned agency to HawkSoft and breaks down what agencies should look for before joining a network—from book ownership and carrier access to contract terms, transparency, and technology investments.

They also dive into the modern agency tech stack, why the AMS is at the center of it all, and the tools helping agencies work smarter, including CRM, texting and VoIP, e-signatures, and streamlined intake solutions.

Plus, Michael talks about HawkSoft’s customer-first “Purple Cow” philosophy and wraps things up with a fun travel-themed round of “Where Would Michael Sit?”

0:00 Networks Look Alike

00:46 Meet Michael Ley

01:37 What Network Relations Means

03:23 From Teacher to Agent

06:01 Networks vs Associations

06:33 Network Pain Points10:35 Agency Network Checklist

15:27 Tech Stack Talk

17:28 Open APIs and Data Ownership

21:35 Must Have Agency Tools

29:15 Purple Cow Branding

32:35 Culture and User Community

34:10 Travel Game Setup

34:54 Aisle vs Window Debate

35:47 Bathroom Row Stories

36:47 Family Travel Tradeoffs

37:10 Accidental Private Jet

38:02 Subway Seat Strategy

39:42 Rental Shuttle Tactics

41:19 Doctor Waiting Room Picks

41:53 Conference Room Power Seats

43:16 Movie Theater Sweet Spots

44:43 Best Seats in the Stadium

47:39 Airplane Selfie Side Eye

49:28 Season Wrap and Sponsor

Nick Berry on TotalCSR, Microlearning, and Unhinged Insurance Marketing | Connected Conversations in InsuranceIn this episode of Connected Conversations in Insurance, host Ray Huang welcomes former co-host Nick Berry back to the show to share what he’s been up to since leaving Canopy Connect, including his new role as head of marketing at TotalCSR.

Nick explains how TotalCSR helps agencies find, assess, and train talent across personal lines, commercial lines, and health and benefits, including license tracking and a microlearning app designed to reinforce knowledge retention—especially for complex commercial topics.

They discuss common resistance to training, the need for ongoing skills checks, and how staying sharp builds trust as a “trusted advisor.” Ray and Nick then shift to marketing, emphasizing outcome-driven ads, creative that doesn’t look like ads, long-form copy, memes, and delivering value to local audiences rather than relying on direct “get a quote” messaging.00:00 Career With Cool People00:41 Podcast Welcome Back02:27 Nick Joins TotalCSR05:17 What TotalCSR Does07:16 Microlearning For Retention09:34 Canopy Connect Ad Break10:38 Custom Learning Paths13:19 Training Resistance And Trust15:02 Golf Practice Analogy17:23 Insurance Mustache Game20:49 Mayhem Ad Love21:07 Guessing Celebrity Jingle22:29 Progressive and Farmers Faces23:44 Canopy Connect Pitch24:49 Top of Funnel Marketing27:36 Unhinged Ads That Work32:26 Value First Local Ads36:06 Marketing Is Everything38:49 Wrap Up and Where to Find39:53 Final Canopy Connect Outro