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Insurance Business Review: Specials Magazine
Every great business decision starts with a question, and for The RiverCross Group, it was this: Can small and mid-sized companies design benefits that truly protect their people while supporting long-term growth? Dottie Allen, Principal and Founder, is at the helm. With over 30 years in the insurance industry and more than 20 years specializing in employee benefits, Allen co-founded The RiverCross Group (originally RiverCross Partners) and continues to lead with a vision that transcends policies and paperwork Dottie imagined a consulting firm as a true ally to business owners, one that aligns insurance strategy with company goals, simplifies complexities, and delivers benefits that make employees feel valued, not just covered. The firm specializes in employee benefits, Key Person insurance, and retirement planning, especially for organizations with decentralized or field-based workforces, such as those in the construction industry, which grapple with long hours, talent scarcity, and tight cost controls. The RiverCross crafts benefits programs that reduce administrative burden, boost retention, and solve real-world challenges. What differentiates The RiverCross is its forward-looking, consultative approach rooted in a deep understanding of each client’s business. Rather than acting as brokers, the team serves as trusted advisors, analyzing specific needs, challenges, and goals to design tailored solutions. The team advocates for self-funded plan options, leverages HR technology to streamline processes, and implements proactive strategies that prepare businesses for growth, acquisitions, or talent retention. Partnering with reputable providers, The RiverCross delivers more than insurance; it drives clarity, communication, and trust-based, long-term relationships. Aligning solutions with immediate needs and future goals ensures clients have the support, tools, and confidence to navigate an ever-changing business and workforce landscape.
Top Business Insurance Service 2025
In 1969, in Pittsburg, Kansas, Ray Ryan started Ryan Insurance—a solitary vision within a single office. More than half a century later that vision continues to flourish as a powerhouse in commercial & personal insurance, with three offices and 15 employees, yet always casting its longest shadow back home, in Pittsburg. Located in a region highly prone to convective storms, the agency evolved with a sharp focus on creativity and thorough risk assessment to provide the needed coverage for their clients. Drawing on over 20 years of personal experience in the Excess and Surplus (E&S) market—and direct access to Lloyd’s of London—Ryan Insurance designs custom coverage solutions where others see only roadblocks. Today the Agency serves a diverse portfolio that spans contractors, public entities, retail, healthcare and nationally recognized manufacturing companies. This ability to solve complex coverage challenges has helped fuel the agency’s steady expansion. Today, its presence stretches to metropolitan hubs like Kansas City, outward to Georgia, Colorado, and Nebraska, and other states, while its soul remains firmly grounded in its small-town beginnings. About 75 percent of its business now comes from commercial clients. Each account, whether next door or a state away, bears the fingerprints of Ryan’s original ethos. That same technical strength and probing curiosity have earned the trust of even the most formidable clients. Whether it’s the world’s second-largest spiral pipe welding operation, a global-scale photo processor, or one of America’s leading fabricators; they all turn to Ryan. Even Mental Health Centers and Community Health Centers deeply complex and personal needs are met with the same standards of care that the agency’s earliest clients received. Technical Strength and Cyber Leadership As stalwart Carriers reassess their state presence and strategy, Ryan’s layered programs, aggregate limits, stop-loss protection, and loss caps hold fast like anchors offer financial protection against loss, helping clients withstand the twists and turns of market volatility and regulatory change. Technical ingenuity, however, is only half the tale. At Ryan, there are no commission-driven silos, no gatekeeping producers; just a seamlessly integrated team, with every member a credentialed insurance professional, each empowered to support any client at any time. Collectively, the team brings over two centuries of experience, drawing from backgrounds in insurance, banking, education, and more, ensuring every challenge is met with seasoned insight. “We offer top-tier expertise with direct access to senior professionals. Clear communication and accountability are standard, and when questions arise, we work quickly to deliver accurate answers on the same day,” says Wally Wilson, CEO.
Top Term Life Insurance Service 2025
Wysh is fundamentally transforming how people access life insurance by seamlessly integrating it into everyday financial products that people already use. The company doesn’t fit neatly into the traditional term life insurance space. Instead, it is a pioneer in the field of embedded financial protection, working alongside banks, credit unions, and fintech companies to offer life insurance as an automatic benefit to their customers. The idea is simple yet revolutionary. When someone opens a checking or savings account with one of Wysh’s partner banks, they automatically receive life insurance coverage worth up to $20,000 without any paperwork, medical exams, or opt-in. It's all taken care of through the existing banking relationship, giving customers peace of mind and protection without the hassle. Alexander Matjanec, CEO, says, "We employ a built-in, not bolted-on model to empower every person to live life to the fullest, with the confidence of financial protection.” This guiding principle drives the company’s efforts to make life insurance more accessible, efficient, and emotionally resonant. The real magic of Wysh lies in those moments of emotional surprise. Imagine the moment when a customer realizes, “Wai I’m actually covered?” For so many, insurance feels like a distant, abstract concept. But for customers of Wyshs partners, it’s an unexpected benefit quietly built into their financial life. Perhaps most importantly, Wysh opens doors for those long excluded from life insurance by making coverage automatic and invisible through everyday banking. The most heartwarming example of this mission is the story of a single mother, a cancer survivor and double amputee, who had long struggled to find life insurance due to her health history. She shared that, before Wysh, she had been unable to secure coverage. But thanks to the company’s partnership with her bank, she was able to receive life insurance just by having a checking account. Wysh’s approach is a game-changer for financial institutions as well. Rather than simply selling an insurance product, the company has found a way to embed financial protection directly into the core services offered by banks and fintechs. This is crucial for banks looking to differentiate themselves in an increasingly competitive market. Wysh’s solution helps them build stronger customer loyalty and attract new clients, all while providing them with a meaningful benefit they didn’t expect—life insurance.
CXO INSIGHTS
Insurance Professionals are the Most Dynamic
Michele Adams, VP, Corporate Functions Finance & EDLC, Walmart[NYSE: WMT]
Navigating the Insurance Maze: Redefining Insurance Renewals and Claims Handling
Kimberly Clifford, Director, Claims Management, EMCOR Group, Inc
Why are Property Insurance Premiums so Unpredictable?
Kelley Shapiro, Vice President, Risk Management, Lightstone
Futureproofing Claims Careers: Adapting to AI in Insurance
Cade Williams, Assistant Vice President, Risk Management-Claims, Marriott Vacations Worldwide
The Keys To Building A Resilient Risk Management Future
Roy Hock, Director of Risk Finance and Casualty Insurance, Valero Energy Corporation
Risk Leadership in a Changing World
Melora Copeland, Director of Insurance, Compass Group USA
Making Employee Benefits Clearer, Simpler and Valued
Laura M. Dilallo, Director of Compensation Benefits, Durham School Services
IN FOCUS
Independent Agencies as Pillars of Community Prosperity
Independent insurance agencies in underserved areas enhance social value, financial literacy, crisis response, and economic resilience by educating individuals and businesses, aiding recovery, and fostering self-sustaining communities.
Reimagining Business Insurance in the Age of Volatility
Businesses are adopting technology-driven insurance solutions to enhance resilience and risk management, shifting from reactive to proactive strategies amidst growing volatility and complexity.
EDITORIAL
Balancing Risk and Resilience in a Changing World
In 2025, the insurance industry stands at a moment of transformation, shaped by changing markets, rapid digital innovation, and rising consumer expectations. What was once a business built on policies and premiums has evolved into one centered on insight, adaptability, and proactive protection. Business insurance has grown increasingly complex as organizations navigate new layers of risk. Cyber threats, supply chain disruptions, and climate-related events are no longer occasional challenges but everyday realities. Insurers are moving beyond traditional indemnity models to deliver proactive risk management and resilience services. With predictive analytics and AI-driven underwriting, they help companies prepare for disruptions before they occur. Life insurance is also transforming. Longer lifespans, shifting financial priorities, and emerging health risks have prompted insurers to rethink their approach. Protection now pairs with investment and wellness, creating hybrid products that link financial security with personal well-being. Policies increasingly feature wellness incentives, data-driven insights, and digital tools that simplify everything from policy issuance to claims. Yet the industry must still balance affordability amid rising healthcare costs and economic uncertainty. Independent insurance agencies remain vital in this evolving landscape. In 2025, they use technology to deliver tailored solutions from multiple carriers while maintaining the personal relationships that set them apart. Agencies embracing embedded platforms, data-informed profiling, and strategic partnerships are finding new ways to stay relevant. Still, they face competition from insurtech startups and ongoing consolidation. The agencies that thrive combine expertise, trust, and agility to meet clients where they are. Across every segment, the industry is learning to balance adaptation with innovation. Success depends not only on operational excellence but also on anticipating what’s next and preparing before it arrives. This edition features insights from Heather C. Pegram, Director, Global Insurance Risk Management, Hanesbrands Inc. and Jennifer M. Pack, Vice President of Risk Management, Hyatt Hotels Corporation. Their perspectives illuminate current conditions and future opportunities. We believe these insights will elevate your decision-making to new heights.
