The Insurance Perspectives Podcast

Hosted by HawkSoft

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Episodes

126

Latest episode

Aug 2026

Language

EN-US

About the show

The Insurance Perspectives podcast provides honest, open, and transparent conversations with members of the independent insurance space about technology partners, mental health, building a tech stack, and more.

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60 recent

August 25, 2026Episode 13032 min

Revisiting ClientCircle with Torey Maerz

In this episode of the IP podcast, Brad Boldt reconnects with Torey Maerz, co-founder and CEO of ClientCircle, for an update on the platform since his last appearance on the podcast in 2024. What started in 2013 as an NPS and referral tool has grown into one of the most customizable marketing automation platforms in the independent agency space. Torey walks through what's new — including a HawkSoft client create integration, a fully customizable user interface, and a robust analytics dashboard that pulls historical data going back before an agency even became a ClientCircle customer. He also shares his measured, refreshingly honest take on AI, why ClientCircle was built on timeless business fundamentals rather than flashy technology, and why the most-used feature on the platform is still the one that asks your clients a single question: how are we doing? Takeaways Tech should solve business problems, not just exist NPS is the most important feature they offer. If you're not using it, you're missing 80% of what the platform can do. Call your detractors. Most companies don't — and that's exactly why it works when you do. Customization is now built in, not bolted on. ClientCircle can be configured to fit any agency's workflow without writing new code. Fundamentals don't go out of style. Welcome new clients, recognize loyal ones, thank those who refer — that's been the foundation since day one. Previous episodes featuring Torey Maerz: ClientCircle Pt. 1 - Apple Podcasts and Spotify ClientCircle Pt. 2 - Apple Podcasts and Spotify Learn more about ClientCircle: https://www.clientcircle.com/ https://www.linkedin.com/company/client-circle/ To get in touch with today's guests, reach out below: Torey Maerz ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

August 18, 2026Episode 12935 min

Revisiting Canopy Connect with Ray Huang

In this episode of the IP Podcast, Brad Boldt sits down with Ray Huang, Vice President of Marketing at Canopy Connect, for an update on everything that's evolved with Canopy since Ray's last IP podcast appearance in 2024. Ray walks listeners through Policy Paste, a Chrome extension that auto-fills carrier forms with collected data; Deck Site, an AI-powered document intelligence tool that parses even 130-page commercial dec page packets into structured data; four flexible sharing paths that meet clients where they are; and a referral partner management feature for agencies working with dealerships, mortgage brokers, and other partners. He also previews what's coming next, including deeper CRM sync and robust reporting. Takeaways Carrier-connected data beats everything else. It comes straight from the source, not from memory. Policy Paste fills carrier forms automatically. No more manually re-entering the same data twice. Meet clients where they are. Four sharing paths mean no client gets left behind. Don't Frankenstein your tech stack. One platform that integrates beats cobbling tools together. Referral partner management is live. Track leads by partner, location, and individual sales rep. Previous episodes featuring Ray Huang: Canopy Connect Pt. 1 - Apple Podcasts and Spotify Canopy Connect Pt. 2 - Apple Podcasts and Spotify Learn more about Canopy Connect: Book a demo https://www.usecanopy.com/ https://www.linkedin.com/company/canopy-connect/ To get in touch with today's guests, reach out below: Ray Huang ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

August 11, 2026Episode 12830 min

Revisiting GloveBox with Ryan Mathisen

In this episode of the Insurance Perspectives podcast, Brad Boldt reconnects with Ryan Mathisen, CEO and co-founder of GloveBox, for an update on everything that's changed since Ryan's last IP podcast appearance. Ryan breaks down GloveBox's four-step adoption playbook and walks through major new features including full white label branding, an embedded quoting marketplace, a new per-user pricing model, and Flows, a full CRM being built natively inside the product. He also shares his take on the AI frenzy and why the fundamentals of sales and service still win. Takeaways GloveBox adoption starts with your website. Four simple steps can get you to 100% adoption. Website, hold recording, out-of-office replies, and the action menu. The new per-user model removes the pressure to scale fast. White label means your brand, not GloveBox's. Flows will let agencies run campaigns, pipelines, and live client messaging in one place. Run your race. Stop looking over the fence at AI, the basics still wins. Previous episodes featuring Ryan Mathisen: GloveBox Pt. 1 - Apple Podcasts and Spotify GloveBox Pt. 2 - Apple Podcasts and Spotify Learn more about GloveBox: https://glovebox.io/ https://www.linkedin.com/company/gloveboxapp/ To get in touch with today's guests, reach out below: Ryan Mathisen ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

July 7, 2026Episode 12734 min

Sense of Community with Jake Dunbar & Greg Fish

In this episode of the Insurance Perspectives Podcast , Brad Boldt sits down with two members of the HawkSoft leadership team: Jake Dunbar, Director of Product Support, and Greg Fish, Director of IT and Information Security. Together they pull back the curtain on one of HawkSoft's defining core values, Sense of Community. They trace its origins back to the early days of the company and explore what it actually looks like in practice. Jake shares how HawkSoft involved its own employees in writing the core values, and why those values have guided executive decisions ever since. Greg and Jake share personal stories that illustrate why, at HawkSoft, sense of community isn't a marketing tagline, it's how decisions get made. Takeaways Core values mean nothing if they don't guide decisions. HawkSoft's core values were built collaboratively. Community includes employees, customers, vendors, and partners. It's not just the people inside the building. Two-minute wait times are a commitment, not a coincidence. HawkSoft invests in support because they mean it. Win-win isn't just a slogan. HawkSoft looks for ways to leave people better off. For more information on HawkSoft's core values, visit: https://www.hawksoft.com/about/core-values/ To get in touch with Jake, Greg, or Brad, reach out below: Jake Dunbar ( click here ) Greg Fish ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

June 30, 2026Episode 12629 min

Cover Desk Pt. 2 - Brad Kaplan

In this episode of the Insurance Perspectives Podcast, host Brad Boldt sits down with Brad Kaplan, president and CEO of Kaplan Insurance Agency. The discuss how Brad's friendship with Andy Priesman led him to become one of Cover Desk's earliest and most enthusiastic adopters, why specialization is the key to getting the most out of virtual staff, and how Cover Desk's accounting feature has allowed his agency to reclaim 15 hours of his month. He also shares the agency's unique niche of insuring performing arts theaters across the country through what they call the "Red Carpet Program." Takeaways Specialize your VAs the same way you specialize your staff. Virtual Assistants (VA) handle the back-end so licensed people can focus on coverage conversations. Add responsibilities gradually. Dump too much at once and nobody wins. Cover Desk handles the IT, onboarding, and tech setup. Just put your toe in the water when it comes to adopting a VA. The investment is low, the upside is high, and you'll find more work for them than you expect. Learn more about Kaplan Insurance Agency: https://www.kaplaninsuranceagency.com/ https://www.facebook.com/KaplanInsuranceAgency https://www.linkedin.com/company/kaplan-insurance-agency-inc-/ To get in touch with today's guests, reach out below: Brad Kaplan ( click here ) Andy Priesman ( click here ) Kelsey Tenaillon ( click here ) Brad Boldt ( click here ) More information about Cover Desk: https://coverdesk.com/ https://www.facebook.com/coverdesk https://www.linkedin.com/company/coverdesk/ ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

June 23, 2026Episode 12532 min

Cover Desk Pt. 1 - Andy Priesman and Kelsey Tenaillon

In this episode of the Insurance Perspectives Podcast, Brad Boldt sits down with Andy Priesman, CEO and founder of Cover Desk, and Kelsey Tenallion, Sr. Director of Business Development of Cover Desk, to talk about how Cover Desk can benefit an independent agent. Andy shares the origin story of Cover Desk, from hiring his first virtual assistant (VA) at Greenway Insurance in 2016 to building a 1,700-person operation. He and Kelsey break down what Cover Desk does differently: in-office infrastructure, end-to-end foundational training, and a client success team that supports agencies well past onboarding. They also get practical about the top duties VAs handle, what makes agencies succeed or fail with virtual staff, and their other services that make Cover Desk more than just a VA provider. Takeaways Cover Desk started as a solution to Andy's own staffing problem. VAs can outperform local hires when given the right training and support. You don't need perfect SOPs to start. Cover Desk will help you build them. Training matters. Agencies that don't invest time upfront won't succeed with any hire. Cover Desk is more than VAs — shared services, accounting, claims, and automation are all services they offer. Treat your VA like a team member, not a task machine. Learn more about Cover Desk: https://coverdesk.com/ https://www.facebook.com/coverdesk https://www.linkedin.com/company/coverdesk/ To get in touch with today's guests, reach out below: Andy Priesman ( click here ) Kelsey Tenaillon ( click here ) Brad Kaplan ( click here ) Brad Boldt ( click here ) More information about Kaplan Insurance Agency: https://www.kaplaninsuranceagency.com/ https://www.facebook.com/KaplanInsuranceAgency https://www.linkedin.com/company/kaplan-insurance-agency-inc-/ ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

June 16, 2026Episode 12420 min

Growing and Leading in a Family Agency with Ashley Winebrenner

In this episode of the Insurance Perspectives Podcast, host Brad Boldt sits down with Ashley Winebrenner, a third-generation insurance professional at Dwyer Insurance Agency in London, Ohio. Ashley shares her winding path to insurance — from working for a CRM company and traveling the world, to nursing school, to stumbling into her dad's agency "just temporarily" and never leaving. Now 14 years in, Ashley is an inaugural member of HawkSoft's Taking Flight Program and is preparing to one day take over the agency her great-grandfather founded in 1931. She opens up about the joys and challenges of working with a parent, navigating a paper-vs-digital standoff, and what it means to carry the weight of a nearly 100-year family legacy. Takeaways Your path doesn't have to be straight. Sometimes you stumble into your purpose. Working with family is a gift, even when it's hard. Change takes patience. Move the agency forward without leaving people behind. Solve the problem before buying the tool. Community closes the knowledge gap. You don't have to figure it out alone. Legacy is both a burden and a privilege. Learn more about Dwyer Insurance Agency: https://www.dwyerinsuranceagency.com/ https://www.facebook.com/DwyerInsAgency To get in touch with today's guest, reach out below: Ashley Winebrenner ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

June 9, 2026Episode 12319 min

Building a Growth-Focused Agency with Jason Larsen

In this episode of the Insurance Perspectives Podcast, Brad Boldt sits down with Jason Larsen, CEO and Risk Advisor at First State Insurance Agency Southwest, to discuss his rapid journey from outside the insurance industry to agency owner. Jason shares how an unexpected career transition led him into insurance during the COVID era, and how strong mentorship, structure, and a willingness to learn helped him step into leadership quickly. He opens up about the challenges of leading through a hard insurance market, building team culture across multiple locations, and balancing growth with thoughtful decision‑making. Takeaways: Strong mentorship can accelerate leadership readiness and ownership transitions. Clear structure and documentation are essential for sustainable agency growth. Culture is built through everyday moments, not just big initiatives. Technology should enhance workflows through integration, not complexity. Community involvement builds trust and long‑term client relationships. Serving people well ultimately drives agency growth. Learn more about First State Insurance Agency Southwest: https://firststateinsurance.net/ https://www.facebook.com/Firststateinsurancesw/ https://www.instagram.com/firststateinsuranceagency/ To get in touch with today's guest, reach out below: Jason Larsen ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

June 2, 2026Episode 12220 min

Growing a Values‑Driven Agency with Jesse Villafranca

In this episode of the Insurance Perspectives Podcast, host Brad Boldt sits down with Jesse Villafranca, owner of Evergreen Insurance, to share the story of building an independent insurance agency from the ground up. Jesse walks through his journey of starting with almost nothing, opening Evergreen Insurance at age 33, and growing it into a respected, community‑focused agency. This conversation dives into family‑first leadership, mentoring the next generation (including bringing his son into the agency), and why doing the right thing for employees and clients always pays dividends. Takeaways Values and family drive long‑term agency success Staying paperless early created lasting efficiency Leadership evolves from client service to team development Mentoring the next generation strengthens continuity Community and relationships fuel sustainable growth Doing the right thing builds trust and loyalty Learn more about Evergreen Insurance: https://evergreen-insurance.com/ https://www.facebook.com/EvergreenInsurance https://www.instagram.com/evergreenvanwa/ To get in touch with today's guest, reach out below: Jesse Villafranca ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/

May 26, 2026Episode 12119 min

Getting to Know HawkSoft's New Director of Partner Integrations with Darrin DeFouw

In this episode of the Insurance Perspectives podcast, host Brad Boldt sits down with Darrin DeFouw, Director of Partner Integrations at HawkSoft, to explore his 20‑year journey with the company and his new role building and maintaining HawkSoft’s partner ecosystem. Darrin shares what it was like joining HawkSoft as one of the company’s first employees, how his experience across every department shaped his perspective, and why partner integrations play a critical role in solving real‑world agency problems. Takeaways Partner integrations solve agency problems holistically. HawkSoft carefully vets partners for quality and fit. Agencies retain full ownership of their data. Cloud architecture enables better, faster integrations. Technology should support real agency workflows. Learn more about HawkSoft and the Partner Program: https://www.hawksoft.com/ https://www.hawksoft.com/about/partners/ https://www.facebook.com/hawksoft/ https://www.instagram.com/hawksoft/ To get in touch with today's guest, reach out below: Darrin DeFouw ( click here ) Brad Boldt ( click here ) ________________________________________________________________________ If you’re looking to reach out to HawkSoft, please email marketing@hawksoft.com. For more information on HawkSoft, visit: https://www.hawksoft.com/ https://www.facebook.com/hawksoft https://x.com/HawkSoft https://instagram.com/hawkSoft Music by AudioCoffee(Denys Kyshchuk): https://www.audiocoffee.net/