Nothing beats experience and perspective.
And that’s exactly what we got from four seasoned professionals—Michael Barrow, Derrick Gleed, Chris Gory, and Blake Waddell—who recently shared their insights in The Benefits Trust’s advisor webinar, unscripted and unplugged.
Their unique journeys and perspectives offer valuable lessons for benefits advisors, providing an industry deep dive anyone looking to make an impact in the dynamic field of employee benefits advising.
Here’s what they had to say:
Michael Barrow: Perseverance and Precision
Michael Barrow’s career began as an underwriter for an insurance company, later advancing to account executive at Manulife before launching his independent practice. His experience highlights the importance of perseverance and strategic relationship-building.
One of his most compelling stories involves an eight-year sales cycle. Michael first worked with a client during his tenure at Manulife. After going independent he maintained contact with the client, and years later, they returned, looking for his expertise. This experience underscores the value of staying present, cultivating relationships, and never burning bridges.
Michael sees commoditization in the industry as an opportunity for advisors who offer real value and education. He emphasizes demonstrating value beyond cost, such as by showcasing stability clauses in out-of-country coverage, which can make all the difference for a client.
Although Michael operates as a solo practitioner, he leverages relationships with providers to ensure efficiency. By setting expectations early, he helps his clients understand how to streamline processes, minimizing delays and miscommunication.
Michael’s advice for prospecting? Business Network International (BNI) has been instrumental for him. This networking model enables members to act as a sales force for one another, resulting in unexpected leads from sources like office cleaners and painters in his area.
For Michael, success means being in a place where he’s able to choose which clients he works with—an aspiration he’s working toward as he grows his business.
Derrick Gleed: Building Strong Relationships
With 41 years of experience, Derrick Gleed’s career began as a wholesaler before he learned from top advisors and eventually built his practice from the ground up. His approach centers on meaningful connections and client loyalty.
Derrick believes a prospect’s potential can be gauged early. If there’s no connection, it’s best not to waste time chasing unproductive leads. For Derrick, loyalty defines the difference between clients and customers. Clients value relationships and trust, while customers often migrate based on price.
The pandemic disrupted these relationships, creating a sense of disconnection. Derrick emphasizes the importance of rebuilding bonds through personal touchpoints, such as visiting business owners where they work.
Derrick’s practice focuses on small and medium-sized businesses, specializing in disability planning, life insurance, and revenue maximization. His team-based approach involves leveraging external partnerships with insurance companies, tax lawyers, and commercial writers to optimize outcomes for clients.
When it comes to marketing, Derrick sees social media as less effective than referral-based approaches. He builds trust by sharing valuable resources with accountants and other professionals, ensuring his name is synonymous with reliability.
For Derrick, success lies in working with people who share mutual comfort and respect. While “retirement” is not in his vocabulary, Derrick plans to eventually transition his business to a valued team member who will take over operations as he remains active, contributing his expertise to the next generation.
Chris Gory: Innovating for Startups
Chris Gory entered the insurance industry in 1995 and transitioned to benefits around 2004. His specialty lies in working with startups, where creativity and innovation are essential.
For Chris, the best part of the benefits business is the people—the clients, the community, and the opportunity to solve creative challenges with his tech clients. However, he notes the industry is grappling with “AI fatigue.” While artificial intelligence has potential, sifting through ineffective tools and buzzwords is a significant challenge.
Chris has successfully adopted AI tools like Draftable to streamline operations, such as creating coverage summaries and tracking policy amendments. This focus on efficiency allows him to remain a one-person operation while using a group MGA for back-office support.
Unlike some of his peers, Chris has found LinkedIn marketing effective, especially when targeting US tech companies. However, other platforms like X (previously Twitter), Instagram, and Facebook have failed to generate leads. His 2025 goal includes creating branded resources to further strengthen his value proposition.
Chris’s best prospecting strategy? Partnering with HR groups aligned with his target industry. He also shares that although he has spent significant time and resources exhibiting at events in his target industries, these investments were ultimately unsuccessful and yielded minimal results.
Success, for Chris, is a balance between financial achievement and a fulfilling personal life. His biggest regret is dedicating resources to partnerships that didn’t produce the expected returns—an important lesson for advisors in measuring ROI.
Blake Waddell: Playing the Long Game
Blake Waddell entered the group benefits field in 2008, having previously worked in the restaurant industry. His straightforward approach and focus on teamwork have become hallmarks of his practice.
Blake defines a great client as someone who engages fully and values the advisor’s contributions. However, not all interactions are smooth. Blake has encountered uncomfortable situations where prospects use his expertise for quotes without intending to work with him, a scenario which advisors would do well to recognize and learn to navigate.
Blake’s practice prioritizes security and efficiency, with significant investments in technology and data protection. His team-based approach ensures that resources are pooled to solve client challenges collaboratively.
When it comes to prospecting, Blake champions long-term relationship building through associations. While the initial years may not yield leads, sustained involvement builds trust and credibility over time.
For Blake, success isn’t confined to professional achievements. Growth, happy staff, and time with family all contribute to his definition of a successful life. One story that exemplifies his impact involves advocating for a CFO’s cancer treatment, which was initially denied. His efforts ultimately secured life-saving coverage, demonstrating the profound difference advisors can make.
Key Takeaways from the Masters
Each speaker brings a unique perspective to the benefits industry, shaped by their backgrounds and experiences:
- Michael Barrow emphasizes perseverance, precision, and the importance of showing value beyond cost.
- Derrick Gleed focuses on meaningful connections and leveraging teamwork for client success.
- Chris Gory highlights innovation and efficiency, particularly for tech-focused startups.
- Blake Waddell underscores the value of long-term relationship building and teamwork.
Their insights showcase a recurring theme: the benefits industry thrives on relationships, adaptability, and a commitment to delivering value.
Whether it’s persevering through long sales cycles, rebuilding connections in a post-pandemic world, adopting innovative tools like AI, or taking a team-based approach to client service, these lessons are invaluable for advisors at any stage of their careers.
If you’re looking to elevate your practice and deliver customized, innovative solutions to your clients, The Benefits Trust is here to help. With a proven track record of supporting advisors in the benefits space, we provide the tools, resources, and expertise you need to succeed.
Ready to take the next step? Contact us today and discover how we can work together to grow your business and strengthen your client relationships.
