Benefits Broker Boost

Plansight
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Benefits Broker Boost is the show that gives employee benefits brokers actionable strategies to grow, scale, and streamline their business. We interview industry experts on how they have grown their agencies and their books of business. You can expect to see marketing strategies, technology successes and systems implementation best practices.  Our goal is that every broker who takes time out of their day to watch or listen to Benefits Broker Boost will walk away with something actionable that they can apply in their business.

  1. May 14

    The Human Advantage: Bridging the Gap Between Modern Tech and Real Connection

    The Human Advantage: Bridging the Gap Between Modern Tech and Real Connection In this interview, Adam Smith, Plansight CMO, and Dennis Walker, Producer at USI, discuss the evolving landscape of the benefits industry. Drawing on his experience as a sales trainer and agency builder, Dennis explains why the most successful brokers are those who combine digital marketing proficiency with old-school, in-person prospecting. The conversation highlights the need to "sound different" in a market saturated with AI-generated outreach and the critical importance of engaging CEOs as strategic partners.   The 14 Areas of Carrier Profit Padding A key theme of the episode is the need for brokers to understand the intricacies of policy design. Dennis reveals that there are 14 specific areas where carriers review rates, and they can "pad profits" in nine of them. By mastering these details, brokers can identify where risk truly exists and help clients transition smoothly from fully insured to self-funded models.   Controlling AI and Preventing Hallucinations While AI is here to stay, brokers must learn how to control it. Dennis shares how he builds "compression restraints" into his prompts to ensure his AI models don't make up case studies out of thin air. The discussion emphasizes using internal, secure models to maintain HIPAA compliance and using AI to reclaim time for strategic consulting rather than just sending more automated emails.   The CEO as a Strategic Peer Dennis challenges brokers to treat executives as their equals. Because CEOs understand finance and budgets, they are often the most receptive to creative benefits strategies when educated properly. By calling CEOs into the room and speaking their language, brokers can move beyond being a vendor and become an indispensable part of the company's long-term strategic plan.   Mentorship and the Future of Care The industry is seeing a divide between legacy brokers and newcomers. Dennis advises younger producers to seek out grit and discipline by learning from veterans who built their businesses before the era of cell phones and text messaging. Looking forward, the conversation touches on the rise of subscription-based care and the return of "concierge-level" services that bring the comfort of the 1950s doctor visit into the modern era.   Ready To Streamline Your Strategic Presentations? Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    54 min

  2. May 7

    The Skeptic’s Guide to Production-Ready AI: Building a High-Trust Engine

    Building a High-Trust AI Engine for Insurance In this episode of the Benefits Broker Boost Podcast, Adam Smith, Plansight CMO, is joined by Brent Combs, the lead engineer behind the Plansight AI engine. With a background in underwriting and a deep passion for mathematical problem-solving, Brent shares the philosophy that drives the platform’s development. The conversation explores the shift from deterministic models to probabilistic AI, the importance of purpose-built AI constraints, and how Plansight achieves 91.09% accuracy on the industry’s most challenging documents.   The Skeptic’s Approach to Innovation Brent explains why he was originally a detractor of general-purpose AI and how he had to prove its validity to himself before building it into the platform. This “trust but verify” approach led to a system that is “guilty until proven innocent,” ensuring that every extracted value is held to a high standard of accuracy and consistency. By choosing the right AI for specific tasks, Plansight avoids the common pitfalls of “drift” found in standard chatbots.   Defining “Shape Accuracy” A core theme of the discussion is the difference between content accuracy and “shape” accuracy. Brent details why Plansight uses a punitive grading system: if the AI correctly identifies data but fails to organize it into the correct plans, classes, or networks, it receives a zero. This ensures that the smartsheeting AI output is production-ready and requires minimal touch from the user.   The Power of Annotations One of the most exciting features discussed is Annotations. This “breadcrumb trail” allows users to click on any extracted data point and instantly see its source in the original document. This feature is designed to close the trust gap, allowing brokers to move from data entry to strategy without losing the ability to validate information with their own eyes.   Unlocking 40% More Time By automating the grueling task of manual spreadsheeting, Plansight helps marketing teams save a conservative 40% of their time. Adam and Brent discuss how this reclaimed time allows brokers to lean into their passions, solve more interesting problems, and provide a better experience for their clients. The goal is to move the industry toward scaling smarter with AI while keeping the human expert at the center of the process.   Ready To Streamline Your Strategic Presentations? Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    53 min

  3. Apr 16

    The Broker 3.0 Blueprint: Beyond the Status Quo

    Rebuilding Health Plan Integrity Through Structure and Specialization   In this episode of the Benefits Broker Boost Podcast, Adam Smith, Plansight CMO, is joined by Ryan Wiggins, Strategist, Employer Health Plan & Benefits at McGriff. Ryan brings over a decade of experience from the carrier side to explain why the modern broker must evolve into a “Broker 3.0,” a specialist who relies on independent thought leadership and a rigid health plan structure rather than simple insurance procurement.   The “Broker 3.0” and the Specialization Shift The industry has moved past the era of the generalist. Ryan discusses how he and his partner built a model focused on specialization. While Ryan masters the health plan and pharmacy risk, his partner focuses on HR technology and voluntary benefits. This allows them to move beyond the spreadsheet and provide high-level consulting that differentiates them in a crowded marketplace.   A staggering 60% of Americans cannot afford an unexpected $1,000 expense. Ryan and Adam explore how high-deductible health plans, while strategically useful, can lead employees into a financial crisis of debt and bankruptcy. Ryan advocates offering diverse options, such as reference-based pricing, to ensure employees have a path to affordable care without compromising their morals.   Navigating the Complexity of Pharmacy Contracts Pharmacy Benefit Manager (PBM) contracts have exploded in length and complexity. Ryan warns that rebates are often just “eye candy” used to distract from the real financial exposure within the contract. He emphasizes the need for renewal automation and reconciliation to ensure carriers are held accountable to the terms they promised.   Data as a Strategic Accelerator Data is often delivered in quarterly “dumps” that offer little actionable insight. Ryan argues that data is only valuable when it is used to accelerate a pre-defined strategy. By understanding organizational trends, like musculoskeletal spend brokers can move from data entry to strategy and provide solutions that actually lower costs and improve health outcomes.   Building a Story and Validating the Book For young producers, Ryan offers a masterclass in building a book of business through social selling and centers of influence. He stresses the importance of “building a story you are willing to take bullets for” and explains why gaining attention and trust is the only way to break through the noise of modern AI-driven prospecting.   Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    51 min

  4. Apr 9

    Redefining the Strategic Brokerage: Moving From Data Points to Digital Signatures

    Redefining the Strategic Brokerage Through AI and Behavioral Data In this episode of the Benefits Broker Boost Podcast, Adam Smith, Plansight CMO, sits down with Becca Johnson, founder of Calliope, to discuss the evolving landscape of benefits marketing. As the industry moves toward a future where strategic brokers win, the conversation focuses on how to use AI and data to move beyond surface-level prospecting and toward high-impact consulting.   The Power of “Digital Signatures” Becca introduces the concept of using AI to identify a company’s “digital signature.” This is a deep look at their plan architecture, carrier history, and employee sentiment. By understanding these underlying factors, brokers can identify prospects with “ecosystem complexity” who are uniquely suited for their specific expertise. This approach allows agencies to stop competing on price alone and start winning through scale, accuracy, and client impact.   Moving Beyond the Spreadsheet with AI A major theme of the discussion is how AI serves as a force multiplier for creative brokers. Rather than using AI to increase the volume of generic outreach, the most successful agencies are using it to surface data that would otherwise take hours to compile. This enables a more authentic and creative disruption in a market that is currently flooded with automated noise.   Omnichannel Outreach and the Human Touch Adam and Becca emphasize that technology should never replace the human element of brokerage. They unpack a disciplined omnichannel strategy that combines LinkedIn engagement, intimate regional events, and context-heavy calling. By betting on yourself and leading with researched value, brokers can turn cold leads into warm partnerships.   Bridging the Innovation Gap With many veteran brokers approaching retirement, agencies face a critical challenge in transferring knowledge to the next generation. Becca explains how AI can act as a “brain trust,” capturing the decades of experience from senior producers and making it accessible to early-career brokers. This ensures that even the newest team members can provide the high-level strategic value that employers now expect.   Ready to See Plansight in Action? Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    34 min

  5. Mar 26

    Beyond the Booklet: How Digital Innovation and Structured Data are Redefining the Consultant Role

    Enhancing Employee Engagement Through Digital Innovation and Structured Data In this episode of the Benefits Broker Boost Podcast, Adam Smith, Plansight CMO, sits down with Landon Fielding, Founder and CEO of Brite. With nearly a decade of experience as a broker, Landon shares the pivotal “aha moment” that led him to abandon the traditional paper benefit guide in favor of a digital-first approach. The conversation explores the critical need for structured data, the role of AI in streamlining workflows, and how the Plansight and Brite integration helps brokers scale with accuracy and impact. The Failure of the Traditional Benefit Guide Landon recounts a 2019 open enrollment meeting where he realized that despite massive spending on custom print materials, employees were completely disengaged. He explains that most paper booklets end up in the trash, leaving HR teams overwhelmed with repetitive questions. This realization shifted his focus toward “zero-to-one” engagement, creating a frictionless, digital environment where employees can learn about their benefits in under ten minutes without the need for complex logins. Prioritizing Relationships in a “Cutthroat” Industry The insurance industry is notoriously competitive and highly dependent on reputation. Landon and Adam discuss why the best agencies prioritize relationships over revenue. By focusing on deep partnerships and ensuring that even the most complex clients have a seamless experience, technology providers and brokers alike can build the trust necessary for long-term broker growth. Rethinking Talent Retention and Perks Benefits have become a primary battleground for talent. Landon shares how his own team looks beyond standard medical plans to lifestyle spending accounts and creative uses for HSAs. By utilizing tools like Truemed, employers can help employees use tax-advantaged funds for fitness and wellness, creating a “cool-to-have” factor that drives real talent attraction and retention. The Future of the Industry in 2026 Looking ahead to the next few years, Landon predicts a massive consolidation of information access points. He emphasizes that while AI will be instrumental in changing broker workflows, its success depends entirely on having structured data. The role of the consultant will shift drastically, and those who haven’t built a digital foundation risk becoming the “Blockbuster” of the benefits world. Ready To Streamline Your Strategic Presentations? Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    46 min

  6. Mar 12

    Beyond the Renewal: Why the Future Belongs to Strategic Benefits Consultants

    In this episode of the Benefits Broker Boost Podcast, Adam Smith is joined by Allison Adams of Gallagher to discuss why the traditional broker model is breaking down and what must replace it. With two decades of experience and a background in education, Allison brings a consultant’s mindset to benefits strategy. The conversation explores why education, intentional communication, and disciplined execution are now mandatory for broker survival as rising healthcare costs and volatile renewals continue to squeeze employers. Strategy Is Not a Buzzword Allison makes it clear that difficult renewal cycles are the new normal rather than an anomaly. Being strategic means staying ahead of claims trends, educating clients year-round, and helping employers understand that renewals reflect long-term decisions rather than just carrier pricing. This proactive approach allows consultants to guide clients through breaking old playbooks to deliver scale, accuracy, and client impact. Education as a Retention Tool Drawing on her history as a teacher and counselor, Allison views continuous education as essential because insurance is often misunderstood by both employers and employees. By teaching clients how to position benefits to address generational gaps and mental health needs, brokers turn communication into a competitive advantage. This philosophy helps brokers move beyond the spreadsheet and win with education and real strategy. Timelines and Accountability A practical takeaway from the episode is the necessity of firm timelines to ensure strategy leads to execution. By establishing deliverables and connect points upfront, brokers protect their credibility and hold all parties accountable. This structure is critical for renewal automation and QA/QC, especially when managing the high pressure of Q4 renewals where carrier data may be limited. Discipline Behind Sustainable Growth Allison attributes success to grit and discipline rather than luck. She maintains a strict cadence, from blocked prospecting time to constant learning through mentorship and internal training. This disciplined habit reflects the future of broker growth where high-performing teams move from bottleneck to buy-in by making every hour count. Ready to See Plansight in Action? Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    40 min

  7. Mar 5

    From Fax Machines to AI: Navigating the Evolution of Benefits Technology

    In this episode, Adam Smith, Plansight CMO, is joined by Michelle Jukoski, EVP of Technology Strategy at Hub International. With a career spanning the move from fax machines to AI, Michelle provides a masterclass in evaluating, implementing, and scaling insurance technology. The conversation focuses on how to move past the “flashy demo” to find tools that solve real operational bottlenecks, the importance of change management, and why the most successful brokers are those who remain curious about the digital evolution. Outcomes Over Features Michelle highlights the most common mistake agencies make: buying for features instead of outcomes. She argues that brokers must perform deep requirements gathering to ensure they are solving their own unique problems rather than someone else’s. By focusing on workflow streamlining, technology becomes a catalyst for growth rather than just another line item in the budget. Human-Centered AI Delivery While AI offers incredible potential for efficiency, Michelle emphasizes the “human in the loop” approach. She cautions against relying on AI bots for buying decisions or complex client strategies without subject matter expertise. The goal of AI should be to eliminate mundane transactional work, allowing human teams to retool and provide higher-level strategic advice to their clients. Standardizing Across the Enterprise For large agencies, rolling out technology across multiple regions requires a delicate balance. Michelle discusses the transition from autonomy to standardization through a technology governance framework. By piloting new platforms and documenting “success stories,” leaders can drive adoption naturally rather than through mandates that might ruffle feathers. Measuring Operational Impact Adoption rates are only the beginning. Michelle explains that the true metrics of success are reduced time to value, lower error rates, and the ability to handle more volume without additional headcount. She suggests measuring hours saved per renewal cycle or RFP as the ultimate indicator of a successful tech implementation. Ready To Streamline Your Strategic Presentations? Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    43 min

  8. Feb 26

    From Data Entry to Strategy: How AI and Smart Workflows are Redefining the Modern Broker

    Enhancing Broker Workflows Through AI and Collaboration In this interview, Adam Smith, Plansight CMO, and Steve Overton, Plansight CPO and Founder, discuss the evolution of the platform and its impact on the insurance industry. With over 25 years of experience as a broker, Steve shares how his background informs the development of tools that transition agencies from manual data entry to strategic consulting. The conversation highlights the synergy between large national brokerages and small boutique shops, the transformative power of AI in extracting quote data, and the critical importance of reclaiming time for client relationships and professional growth. The Evolution of Dedicated Workflows Over the last two years, Plansight has shifted from a collection of individual features to a system of guided, dedicated workflows. Steve explains that while they initially built many requested features, users sometimes struggled to see how they connected. The current platform now provides a streamlined path from A to Z, making it nearly impossible for users to get lost. This evolution is described as making the software unrecognizable and a totally different animal compared to its versions from just a few years ago. AI and the End of Manual Data Entry One of the most significant technological leaps in the platform is the integration of AI to handle data extraction. This technology reads and pulls data directly from quote documents, addressing the industry's long standing struggle with tedious manual data entry. By injecting complex AI directly into the existing workflow, the software performs the heavy lifting behind the scenes. This allows users to focus on making easy decisions rather than worrying about the mechanics of how the technology operates. A Collaborative Brain Trust of Brokerages Plansight serves a wide range of clients, from top five national agencies to small three person shops. This diversity creates a unique brain trust where feedback from all levels benefits every user. Small brokers gain the advantage of workflow efficiencies inspired by large competitors, while large agencies benefit from the niche suggestions and small boutique fixes that improve overall usability. The system remains highly configurable, ensuring that essentially no two users have the same experience while still following the same high standard processes. Maximizing Time for Strategic Consulting The primary value of Plansight is giving hours back to the brokerage team for every RFP and renewal. Steve and Adam discuss how this saved time allows brokers to move away from being numbers bots or data entry clerks and toward becoming true consultants. Whether it is managing a massive book of 178 groups like power user Whitney or adding additional lines like WorkSight and Life coverage, the goal is to provide the bandwidth needed to study industry trends and nurture long term client strategies. Customer Driven Innovation The development of Plansight is deeply rooted in a constant feedback loop with its users. Steve maintains a unique connection with customers, often taking direct feedback via text or regular pow-wows with power users to influence the product roadmap. This collaborative approach ensures that the software solves mission critical problems, such as presenting renewals and comparing quotes quickly. The result is a platform built on hard lessons and trial and error, refined specifically to help new industry hires get up and running as fast as 20 year veterans. Ready To Streamline Your Strategic Presentations? Plansight is the only end-to-end benefits marketing platform that uses AI and automation to ensure every renewal and RFP is consistent, accurate, and fast. By taking the manual work out of benefit planning, Plansight helps you stay ahead of the curve and deliver faster, smarter results to your clients. Visit Plansight to learn more about making your brokerage more efficient.

    14 min
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About

Benefits Broker Boost is the show that gives employee benefits brokers actionable strategies to grow, scale, and streamline their business. We interview industry experts on how they have grown their agencies and their books of business. You can expect to see marketing strategies, technology successes and systems implementation best practices.  Our goal is that every broker who takes time out of their day to watch or listen to Benefits Broker Boost will walk away with something actionable that they can apply in their business.

Information

  • Creator
    Plansight
  • Years Active
    2025 - 2026
  • Episodes
    23
  • Rating
    Clean
  • Copyright
    © Copyright 2025 All rights reserved.
  • Show Website
    Benefits Broker Boost

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