Phil Fierro, the visionary Managing Director at Risk Strategies, is a master of strategic agility, effortlessly navigating the labyrinth of organizational complexities. He seamlessly transitions from the lofty heights of restructuring to the granular details of drafting employee memos, demonstrating a remarkable ability to balance the big picture with the day-to-day. Recognizing that fierce competition demands a paradigm shift, Phil’s leadership helped increase Risk Strategies’ growth trajectory. He came on board in 2022 when the company had already secured a coveted position as the 9th largest privately held broker in the U.S., offering comprehensive risk management advice, insurance, and reinsurance placement. His tenacious commitment to tailoring his approach to the demands of a high-growth environment has been instrumental in delivering comprehensive risk management solutions and promoting a culture of innovation.
It can be described as a calculated leap into leadership when one gets to learn about the chronology of events in his professional life. His journey, marked by well-considered decisions and pivotal moments, reflects a deep understanding of the insurance and brokerage industries.
His career began humbly at NYLCare, NY Life’s benefits division, where he started in the mailroom. Through perseverance, he ascended to manage the department, leaving only when they were acquired by another company. His next move took him to a Top 25 Consulting Firm in New York, where he gained significant experience as a small group account manager. This foundation on the client side paved the way for his transition to United Healthcare as a Small Group Sales Representative. In 2003, he was named the top sales rep in the nation—a recognition that reinforced his capabilities and opened new doors.
It was during this period that Phil’s strategy shifted. “Since I worked with many brokers, I decided it was time to take a leap to that other side of the business and become a broker,” he shares. That leap led to the creation of Fierro Consulting Inc. in 2016, a key turning point in his career. Here, he met Linda Marra, President of Ladmar Associates, and together, they formed a partnership that would lead to the creation of The Ladmar Group in 2019. Their collaborative efforts culminated in their acquisition by Risk Strategies in December 2022, where they both now serve as Managing Directors, driving success with determination.
It’s time to pick up inspiring moments from Phil’s life as he shares in this exclusive interview:
Risk Strategies: A Leading Force in Risk Management
Risk Strategies is the 9th largest privately held insurance brokerage in the U.S., specializing in comprehensive risk management, insurance, and reinsurance solutions. With over 30 specialty practices, the company offers in-depth industry expertise and customized strategies tailored to address the unique challenges of businesses. Serving a wide range of industries, from healthcare and financial services to aviation and entertainment, Risk Strategies provides specialized insight and practical advice to manage complex risks. The company’s network of over 500 carrier partners, 150+ offices, and a strong client retention rate of 92% exemplify its commitment to delivering top-tier solutions across five core business segments: Property & Casualty, Employee Benefits, Private Client Services, Consulting Services, and Financial & Wealth Solutions. Placing over $15 billion in premiums annually, Risk Strategies is recognized for its client-centric approach, offering services that include claims advocacy, analytics, and safety programs, ensuring businesses are equipped to face the future confidently.
Professional Roadblocks and The Way-outs
Every successful enterprise navigates a unique tempest. Phil’s journey was no exception. “2013 was a tough year,” he recalls. He faced the dual challenges of relocating his business and the looming uncertainty of healthcare reform. Despite the turbulent waters, Phil’s methodical adaptability and relentless determination thrust him to unprecedented heights.
He diversified his offerings, acquiring licenses in P&C and Medicare. Through aggressive marketing and strategic partnerships, Phil rebuilt his client base and surpassed his previous earnings. Sharing this commendable breakthrough, he notes, “By the end of 2015, I was making more money than I had ever in my career.”
A Milestone Achievement at Risk Strategies
As one of “The 10 Most Empowering Business Leaders to Watch in 2024,” Phil’ Fierro’s success is a masterclass in resilience and tactical moves. When asked about his most notable accomplishment at Risk Strategies, Phil acknowledges their relatively short tenure but proudly highlights a key achievement. At the 2024 National Sales Conference, Ladmar was recognized as one of the top brokers in the nation for surpassing its ambitious 2023 sales targets. This recognition underscores Risk Strategies’ commitment to delivering exceptional value and innovative solutions to its clients, solidifying its position as a leading force in the risk management industry.
Fostering Collaboration and Growth at Risk Strategies
“Risk Strategies makes it easy to connect with other members of the company,” explains Phil, “through their national sales calls and events, company portal, conferences, and webinars.” A dedicated resource for his peers, particularly in the Northeast region, he focuses on Employee Benefits and Medicare. With the company’s rapid expansion, he aims to contribute to his community by leveraging Risk Strategies’ positive impact. By assisting others, this senior director believes they can cultivate new client relationships and elevate Risk Strategies’ presence in the area.
Phil’s Leadership Philosophy: Be Bold, Be Different
Phil’s leadership philosophy at Risk Strategies is deeply rooted in the belief that standing out is crucial. He urges to “be bold, be different, don’t sound like every other broker in the industry,” emphasizing the importance of individuality and innovation. This mindset extends beyond his own work and into how he manages his team. The veteran leader fosters a supportive environment by maintaining an open-door policy, ensuring that team members always feel comfortable seeking guidance or asking questions. He understands transparency and accessibility are vital for building trust and achieving success. According to him, “Good things have a way of catching up to you if you work hard and you’re honest.”
For him, the fuel to his relentless drive is deeply rooted in his quest for ‘financial stability.’ Having started from the bottom and built his career entirely through his own efforts, he underlines that pursuing financial success remains a primary motivator. In Phil’s case, making money is not just about accumulating wealth; it’s a testament to his ability to overcome challenges and achieve his goals. This continuous pursuit of success is both a personal and professional commitment, reflecting his dedication to maintaining and expanding his achievements.
Secret to Work-Life Balance
Striking a balance between professional and personal life is challenging, especially in demanding roles. As a seasoned professional, Phil has mastered this art. He prioritizes scheduling dedicated work hours to ensure he doesn’t neglect his personal life. But his biggest support comes from his wife, Jessie. Her experience in the field gives her empathy for his workload, and she’s a constant source of encouragement. As Phil puts it, “I have a loving and supportive wife, Jessie, who is also in the industry, so she understands the hardships I endure, as we both do.” Their mutual understanding and support have been instrumental in navigating the ups and downs of their busy lives.
Shaping the Future of Insurance: Risk Strategies’ Strategic Adaptation
Phil sees the future of the insurance sector being shaped by several key trends. The industry’s rapid evolution is driven by increasing demand for specialized coverage, notably in Employee Benefits and Medicare. Risk Strategies is actively expanding its footprint and capabilities to stay at the forefront. As one of the top 10 brokerages in the nation, the company is leveraging its size and influence to lead in the market.
The Managing Director highlights that Risk Strategies focuses on strategic growth through acquisitions and enhancing its offerings in specialty markets. A major initiative is the creation of a department of subject matter experts dedicated to all fields of insurance. “We are creating a department of subject matter experts to help educate HR specialists so they can assist their employees,” Phil notes. This team aims to better support employees with complex insurance needs. Additionally, in the New York region, Risk Strategies is introducing Group Retiree Coverage to address the needs of employees nearing retirement or reducing their hours. This coverage will help maintain strong benefits while assisting employers in managing costs.
Vision for Future Generations in Insurance
This prescient director envisions Risk Strategies’ internship program as a climactic initiative for shaping the insurance industry’s future. The company welcomes a select group of students each summer, providing them with hands-on experience and industry insights. Phil highlights the impact of this program through his recent experience training a Penn State student. He notes the student’s enthusiasm and receptiveness to learning and listening, underscoring the program’s effectiveness in inspiring and educating the next generation of industry professionals. According to Phil, this proactive approach not only nurtures talent but also ensures that the future workforce is well-prepared and motivated.
Staying Current and Relevant in a Dynamic Industry
Phil underscores the imperative of staying abreast of industry developments and consistently refining one’s expertise. In today’s rapidly evolving world, maintaining a competitive edge is essential. To flourish in any domain, merely resting on one’s laurels is insufficient. By staying informed about the latest trends and continuously enhancing their skills, individuals equip themselves with the knowledge and abilities necessary to navigate change, capitalize on emerging opportunities, and remain indispensable assets in their respective fields. Risk Strategies fosters this approach by offering a plethora of resources, including comprehensive learning platforms, personalized regional sessions, informative bulletins, and enlightening webinars. Phil says, “We are constantly learning as well as educating our clients and prospects.” He highlights the recent completion of a Tony Cole Sales series, which has introduced innovative selling strategies. Phil notes that fresh perspectives are essential, as everyone occasionally needs a boost to reinvigorate their approach and continue pushing forward in their efforts.
Teamwork Makes the Dream Work: A Proud Collaborative Triumph
When asked about a project he is particularly proud of, the insurance industry stalwart highlights a standout collaborative effort at Risk Strategies that overcame significant challenges and was completed before the company’s acquisition.
In September 2022, Ladmar, Phil and Linda’s company at the time, were tasked with securing a new account in Texas—a challenge given they had no presence in the state. However, they gained an entry point due to a strong relationship with the HR manager. The real challenge was demonstrating their capability to manage a large, out-of-state group.
As the process unfolded, Ladmar was acquired by Risk Strategies in December 2022, which proved to be a turning point. With access to the national platform, they utilized new resources, established key market relationships with carriers in Texas, and collaborated with the Risk Strategies account management team. Over several months, they conducted extensive research and, after three executive presentations to HR, management, and the Board of Directors, successfully secured the account in June 2023.
“Without our new relationship with Risk,” Phil shares, “I don’t believe we would have won the case, so it was true collaboration.”
Leadership Advice for Aspiring Insurance Professionals
For young professionals aiming to excel in the dynamic world of insurance, Phil stresses the importance of relentless ambition and growth. He advises them to never settle, encouraging a mindset of continuous improvement. If they find themselves unhappy or without growth opportunities, Phil urges them to move forward and seek new challenges. He believes personal development is just as crucial as climbing the corporate ladder, pushing them to advance within their current role while always focusing on becoming better individuals. He ultimately encourages these aspirants by saying, “Strive to become an expert at what you do and make sure people know what you do and how they can get a hold of you.”
A Legacy of Leadership and Innovation
An adept strategist who’s goal it is to expand the Risk Strategies’ footprint across Long Island and establish the company as a National Medicare industry powerhouse, Phil envisions leaving a lasting impact on both the organization and the insurance sector as a whole.
This Insurance industry pro hopes to be remembered as someone who embodied commitment, reliability, and deep knowledge within the field while maintaining a reputation for fairness and honesty.
In his role, Phil has always been “a hustler who never settles and constantly thinks of new ways to meet new people.” In response to emerging trends, reinvention has been a core part of his approach. For Phil, his ultimate goal has always been the company’s success, and his dedication to personal and professional growth reflects that enduring commitment.
