The Insurance Perspectives Podcast

In this episode of the Insurance Perspectives Podcast, Jeff White, HawkSoft's social media manager, kicks off a three-part series on social media content creation. Matt Larson, President of Cal Rose Insurance in Everett, Washington, joins the podcast to talk about his content strategy, advice for fellow agents and more. What started as a way to tell people he was "insurance guy" turned into a full content strategy that has generated real leads, built genuine community trust, and made him one of the most recognized independent agents in his market. Matt shares his platform-by-platform strategy, why engagement beats views every...

In this episode of the Insurance Perspectives Podcast, host Michael Ley reconnects with Dominic Piccirillo and Stanley Meytin, co-founders of Elevate Teams, for an update since their last podcast appearance in March 2025. Elevate Teams has always been known for its rigorous pre-training model but the big news this time is Elevate Plus, a new offering that audits an agency's existing workflows, builds out SOPs, and trains the incoming VA on how the agency actually operates. Dominic and Stanley also get into their matchmaking philosophy, why low churn is the real proof point, their take on AI, and why the...

In this episode of the Insurance Perspectives podcast, host Michael Ley sits down with Raution Jaiswal, founder and CEO of InsuredMine, for an update since the platform's last appearance in January 2024. What started as a CRM has evolved into what Raution calls a "system of intelligence" — a platform that sits on top of your AMS and helps agencies sell more, retain more, and understand their book of business at a level that wasn't possible before. Raution walks through several major AI developments, including Iva, an AI voice agent that takes and makes calls when your team is unavailable; a Cl...

In this episode of the IP podcast, Brad Boldt reconnects with Seth Zaremba, founder and CEO of b atomic, for an update on everything that's evolved since Seth's last appearance on the podcast in 2025. b atomic started as a push-button endorsement tool and has grown into a full AMS-integrated automation platform that plugs directly into HawkSoft. Seth walks through how Service Center works in practice — from vehicle changes that go from 15 minutes to 15 seconds, to fully automated personal lines remarketing that lands bind quotes inside HawkSoft 30 days before renewal.

Takeaways

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 ta...

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...

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

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...

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."

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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...

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...

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.

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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

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

In this episode of the Insurance Perspectives podcast, host Brad Boldt is joined by Michael Ley, HawkSoft Director of Networks, to discuss choosing the right network and conducting effective technology audits. Michael shares practical guidance on how agencies should evaluate networks, identify red flags in contracts, and avoid common mistakes that can lead to costly exits or misalignment. The conversation concludes with a discussion on technology audits and how agencies can assess their current tech stack, avoid “shiny object syndrome,” and ensure new tools actually support workflows and growth goals.

Takeaways

In this episode of the Insurance Perspectives podcast, host Brad Boldt sits down with Dirk and Beth Zeigler of Zeigler Insurance to discuss the realities of building and running an independent insurance agency as a married couple. Dirk and Beth share their journey from the early days of starting the agency out of necessity, through the leap from a captive model to independence, and into the long‑term growth of a community‑focused agency. They open up about the challenges of working alongside a spouse, setting boundaries between work and home, navigating major business decisions together, and learning to trus...

In this episode of the Insurance Perspectives podcast, Megan Ashmead Pacella and Kim Ashmead Leyens share insights on managing family dynamics within their independent insurance agency. They discuss the evolution of their agency, the challenges and rewards of working with family, and strategies for effective partnership and leadership.

Takeways

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In this episode of the Insurance Perspectives podcast, Brad Boldt speaks with Dee and Jackie Zampella of EAB Insurance Group about leading and modernizing a family‑owned independent insurance agency. They discuss working together as a family, leadership, agency technology, and how tools like HawkSoft helped modernize operations while preserving a strong, client‑first culture.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt interviews David and Grayson Carothers from Florida Risk Partners, exploring the unique dynamics of working with family in the insurance industry. They discuss the evolution of their agency, the onboarding process of Grayson into the business, and the importance of mentorship and building relationships with clients. The conversation highlights the challenges and rewards of family-run businesses, emphasizing the significance of clear communication and understanding in maintaining both personal and professional relationships.

Takeaways

In this episode of the Insurance Perspectives podcast, host Brad Boldt sits down with Dean Bowen of Patriotic Insurance Group to explore how Sembley functions inside a real independent agency. Dean shares his journey into the insurance industry, what it was like joining his family’s agency, and how Sembley has transformed their workflows. The conversation highlights the practical, day‑to‑day impact of Sembley, including streamlined intake processes, simplified ACORD creation, reduced manual work, and improved client communication.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Dean Bowen and Joe Ems to explore how Sembley is transforming insurance workflows. They discuss Sembley's mission to eliminate duplicate data entry, streamline ACORD and supplemental forms, leverage document‑reading AI, and deeply integrate with systems like HawkSoft, AgencyZoom, and Canopy Connect. Listeners get a behind‑the‑scenes look at how Sembley was founded, how the product has rapidly evolved over just two years, and what’s coming next—from proposal automation to pushing data directly into carrier portals.

 Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt interviews Linda Fisher, founder of Cardinal Insurance Group. They discuss the agency's growth strategies, the challenges faced during the hard market, and the importance of restructuring and departmentalization. Linda shares insights on leveraging technology and AI to enhance efficiency and the role of mentorship in developing the next generation of insurance agents.

 Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Billy Wagner to discuss Brightway Insurance's focus on team development, culture, and strategies for growth in 2026. Billy shares insights on building a high-performing team, the importance of a positive culture, the rigorous hiring process for A-players, and the comprehensive benefits offered to employees. He emphasizes the significance of metrics and accountability in performance, the development of future leaders, and the agency's vision for community impact.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt interviews Michael Cruz, founder of Foresight Insurance, discussing the agency's growth strategies, their implementation of a four-day work week, and the challenges faced in the insurance market. Michael shares insights on productivity, client retention, and the role of technology and AI in enhancing agency operations. The conversation emphasizes the importance of adapting to market conditions and leveraging innovative practices for sustainable growth in 2026.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Jill Hall and Suzy Tawes from Landmark Insurance and Financial Group to discuss their experiences with Mivation. The conversation covers the challenges of commission management, the efficiency gains achieved through Mivation, and the overall value it brings to their agency. Jill shares insights on how Mivation has transformed their workflows, reduced stress, and improved agent satisfaction. The episode also touches on future enhancements and the importance of trust in financial reporting.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Seth Preus from Mivation to discuss what they can do to help independent agents. The conversation covers Mivation's innovative approach to automating commission reconciliation, the challenges faced by independent agents, and the importance of transparency and performance tracking in enhancing agency efficiency. The guests share insights on the onboarding experience with Mivation and how their tools can significantly reduce the time spent on commission processing, ultimately allowing agents to focus on sales and client relationships.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Dale Steinke, Director of Agent for the Future Advisors at Liberty Mutual, to discuss the transformative role of AI in the insurance industry. Dale emphasizes the importance of independent agents adapting to technological advancements, particularly AI, to enhance their business operations. He shares insights from his extensive experience working with agents, highlighting the need for a structured approach to implementing AI, including data security, staff training, and establishing usage policies.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with HawkSoft leadership, Sean Hawkins and Matt Aman, to discuss the evolving role of artificial intelligence (AI) in the insurance industry and at HawkSoft. The conversation begins with an overview of HawkSoft's approach to AI, emphasizing the importance of understanding its limitations and potential pitfalls. They explore various AI functionalities that could streamline operations, such as automated reporting and policy comparisons. The episode concludes with a reflection on the future of AI in the insurance sector, emphasizing the need for responsible implementation and the importance of maintaining...

In this episode, the conversation revolves around the integration of Cara at LeDoux Insurance. Host Brad Boldt interviews the agency's principal, Dawn Roberts, about her experience and how Cara has transformed their operations by improving call handling and client interactions. The discussion also covers the agency's history, the challenges faced in customer service, best practices for implementing AI solutions, and the overall value that Cara brings to the agency.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt sits down with Nikhil Kansal, co-founder and CTO of Cara, to talk about how Cara helps independent agents. They discuss the transformative role of AI in the insurance industry, focusing on Cara AI's capabilities to automate back-office tasks, enhance client interactions, and streamline the quoting process. The conversation highlights the importance of technology in improving agency efficiency and the practical applications of AI in everyday insurance operations.

Takeaways

In this episode of the Insurance Perspectives podcast, host Brad Boldt chats with Jeff Arnold to discuss the integration of AI in the insurance industry. Jeff shares his journey from a failed acting career to becoming a successful insurance agency owner, emphasizing the importance of using AI to enhance customer service and operational efficiency. The conversation explores the balance between leveraging technology and maintaining the human element in insurance, as well as the future of AI in the industry.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt welcomes Amrish Singh to discuss Liberate and its transformative impact on the insurance industry. They explore the mission of Liberate, its differentiating factors, the importance of data ownership, and how AI enhances human capabilities in insurance agencies. The conversation also touches on the integration with HawkSoft, the challenges faced in the independent agency channel, and the passion that drives professionals in the insurance sector.

Takeaways

In this episode of the Insurance Perspective podcast, Brad Boldt hosts Chris Fitts and Scott Smith to discuss Fitts Insurance Agency's experience with Jump Suit Group. The conversation covers the evolution of the agency, the challenges of transitioning leadership, the importance of technology solutions, and the benefits of automation in client communication. Chris emphasizes the value of building trust with technology partners and the need for effective marketing strategies to compete in a competitive landscape.

Takeaways

In this episode of the Insurance Perspectives podcast, Brad Boldt welcomes Scott Smith and Chris Fitts to discuss the role of Jump Suit Group in providing digital marketing and lead generation services for independent insurance agents. The conversation covers the importance of a strong digital presence, the challenges faced by independent agents, and the need for realistic expectations in digital marketing efforts. They explore the integration of Jump Suit Group with HawkSoft, emphasizing the benefits of automation and streamlined processes for agents.

Takeaways

In this episode of the Insurance Perspectives podcast, Michael Ley hosts and talks to Sean Hawkins and Matt Aman about HawkSoft's core value, "Continuous Innovation." They explore the importance of grassroots innovation, the role of team empowerment, and how feedback from users drives product development. The conversation highlights real-world examples of innovation, the challenges of embracing change, and the exciting features on the horizon at HawkSoft.

Takeaways

In this episode of the Insurance Perspectives podcast, guest host Ciara Gravier speaks with Tinsley English, an operations executive and expert in female leadership development. Tinsley shares her journey into the insurance industry, the importance of people in the business, and her G-Force code, which emphasizes grit, growth, and gumption. Tinsley has a mission to, "... help 1 million women uncover their God-given brilliance and transition from lone achievers to 24-CARAT Leaders."

Takeaways

In this episode of the Insurance Perspectives podcast, host Ciara Gravier speaks with Lisa Hengel, owner of Willow Wood Insurance Agency. They discuss Lisa's journey in the insurance industry, her experience with the Goldman Sachs 10K Small Business Program, and the importance of supporting women in ownership roles within the industry. Lisa shares insights on navigating acquisitions, the challenges of scaling a business, and the role of technology in modern insurance practices.

Takeaways

In this episode of the Insurance Perspective podcast, guest host Ciara Gravier speaks with Kasey Connors, executive director of the Agents Council for Technology (ACT), about her journey into the insurance industry, the importance of relationships, and the challenges of technology adoption. They discuss the role of ACT in supporting technology in insurance, advice for new agents, and the significance of mentorship and networking, especially for women in the industry. 

Takeaways

In this episode of the Insurance Perspectives podcast hosted by Michael Ley, 
director of network relations at HawkSoft, we celebrate 30 years of HawkSoft by speaking with a few of the long-tenured employees at the company. The conversation highlights their unique journeys, the core values that define the company culture, the challenges faced in providing exceptional customer service, and the lessons learned throughout their careers at HawkSoft.

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In this episode of the Insurance Perspectives podcast, Kenny Hendricks speaks with Landon Bentham, President and CEO of Callahan and Rice Insurance Group, about the intricacies of agency perpetuation. They discuss Landon's journey within the agency, the importance of leadership during transitions, and the key lessons learned throughout the perpetuation process. Landon shares insights on avoiding common pitfalls, the significance of effective communication, and the current status of the agency as it continues to grow and evolve.

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