About Us

Leadership

Roosevelt Road’s executive leadership team includes many of the most respected leaders in the insurance industry. Combined with our industry program specialists, you have access a host of financial, each committed to further developing their knowledge and expertise in their respective fields.

Roosevelt Road
Dan Hickey

Dan Hickey

Founder
Rick Ecklord

Rick Ecklord

CFO
Thomas Kelly

Thomas Kelly

General Counsel
Greg Jablonsky

Greg Jablonsky

CIO
Jim Kilduff

Jim Kilduff

Director of Reinsurance
Sean McDonnell

Sean McDonnell

CMO
Joe Mercurio Jr

Joe Mercurio Jr

SVP, Loss Control
Samuel Hickey, CRIS

Samuel Hickey, CRIS

VP of Broker Relations-East Coast
Jennifer Pymm

Jennifer Pymm

Assoc General Counsel of Casualty
Lily Hickey

Lily Hickey

Director of Claims
Greg Mosher

Greg Mosher

CEO
Carol Ryan

Carol Ryan

Underwriting
Drew Ott

Drew Ott

Marketing
Bryan Baird, RPLU

Bryan Baird, RPLU

CEO
Anthony Baird

Anthony Baird

Operations
Rian Girard, CPCU

Rian Girard, CPCU

Underwriting
Jeff Feldman

Jeff Feldman

Senior Vice President, Claims
Nick Markgjonaj

Nick Markgjonaj

Senior Casualty Underwriter
Kymbra Lier, CLCS, TCS

Kymbra Lier, CLCS, TCS

Associate Underwriter
Al Gutierrez

Al Gutierrez

VP of Broker Relations-West Coast

Dan Hickey

Founder

To the International Insurance Industry, Daniel Hickey brings 27 years of diverse insurance experience across the Property & Casualty industry, which includes the independent agency system, Domestic Insurance Company and unprecedented understanding of the Bermuda Re-insurance marketplace.  He graduated from Northeastern University in 1990 with a B.A. in Business Administration, majoring in finance with honors, (Cum Laude).Daniel served as CEO and Chairman of Majestic Holdings, LLC, a company he took public in 2005. Mr. Hickey led the negotiation and acquisition of Majestic Insurance Company. He succeeded in turning a B++ company into an A- “AM Best” rated company, grew premiums from roughly $50 million to over $150 million, and expanded the business into new states including NJ, NY, NV, and FL.Daniel Hickey Jr. has a thorough understanding of the intricacies of the insurance model from top to bottom, understands the role each key discipline plays in a successful operation and possesses the keen ability and vision to build and execute an effective company strategy.

Phone

845-453-1787

Rick Ecklord

CFO

Rick Ecklord is the Chief Financial Officer and joined in 2019 bringing 25 years of experience to the firm. Prior to joining TPM, Mr. Ecklord served as the President and COO of Sandell Re, Ltd. a Class 3A Bermuda Reinsurer, which he founded in 2014. During this period Mr. Ecklord also created a Joint Venture, SOBC Sandell, which focused on mid-cap investments in the insurance run-off space. He was with Sandell Asset Management, a Global Event Driven Hedge Fund, for 18 years where he was a Partner and Senior Managing Director. In this capacity he led investments in the Merger Arbitrage universe.Previously, Mr. Ecklord worked in Equity Derivative roles for Goldman Sachs, SLK Capital Markets and was a member of the American Stock Exchange. Mr. Ecklord graduated from The Citadel, The Military College of South Carolina in 1995 with a BS in Business Administration with a concentration in Finance.

Phone

917-617-8630

Thomas Kelly

General Counsel

Tom Kelly is a New York State admitted attorney who has practiced in New York for over 35 years. He is admitted to the Southern and Northern District Federal Courts as well as the 2nd Circuit Court of Appeals.Tom brings a wide range of experience to the company as his area of expertise is in personal injury litigation, insurance coverage disputes, and regulatory compliance. Tom has extensive experience in handling Labor Law Claims and will work hand in hand with our TPA and outside counsel to vigorously defend these actions. He is married with three children and sits on various civic minded boards in the Greater New York Area.Throughout his career, he has represented a number of insurance carriers including Main Street America, Liberty Mutual and Lloyds of London. He also represents several municipalities in defense of personal injury and constitutional violation claims including the City of Poughkeepsie Police, Town of Poughkeepsie and County of Dutchess.

Phone

914-474-1475

Greg Jablonsky

CIO

Greg Jablonsky has served as CIO of Roosevelt Road Specialty since 2021 and manages IT strategy and operations for all subsidiaries, including Roosevelt Road Reinsurance. His unique strength lies in attentive listening and effective communication. Greg is passionate about assisting and learning across business areas and routinely collaborates with the CFO on actuarial analyses. His fresh perspective enables seamless connections with different departments, enhancing overall efficiency. The most challenging aspect of Greg’s job is substantiating the time-intensive nature of IT projects to all parties involved. He takes pride in his career growth, maintaining a "What's Next" mindset. With eight years as a CIO, Greg's diverse experience includes roles at the New York Power Authority and IBM. He holds a Bachelor of Science in Information Systems from Pace University and enjoys golfing with members of the Buffalo Bills outside work.

Phone

332-345-3303

Jim Kilduff

Director of Reinsurance

Phone

682-712-6205

Sean McDonnell

CMO

Sean McDonnell has over 30 years of insurance experience and joins TPM after (10) years at RT Specialty where he brokered directors & officers and professional liability coverage. He began his career at Chubb & Son in 1989 as an excess umbrella underwriter, working in offices throughout Upstate NY and New York city. In 1995, Sean then joined Constitution Reinsurance in New York City as a facultative casualty underwriter and concentrated on general liability, umbrella and professional liability. In 2000, Sean then moved back to his hometown of Buffalo, NY and worked for American International Group as a Business Development Manager until late 2001 when joined Compensation Risk Managers, which was founded by Dan Hickey. Sean was regional sales manager and worked with independent agents throughout NY and NJ.

Phone

716-361-9505

Joe Mercurio Jr

SVP, Loss Control

Joe Mercurio has spent the last eight years of his career with Pro Safety Services, LLC as a Senior Safety Consultant. His experiences there include many big projects, such as:
  • Structure Tone- 10 Columbus Circle (SSM)
  • Roger & Sons/Turner Construction- 66 Hudson Blvd (SSM)
  • AECOM Tishman- Hudson Yards Tower E (CSFSM)
  • W&W Steel Erectors- Hudson Yards Retail and Tower A(Safety Manager)
  • Yonkers Contracting- Montreign Resort Casino at Adelaar (Safety Rep.)
  • Belway Electric- Regeneron Pharmaceuticals (Safety Rep.)
  • Lendlease- Winthrop University Hospital (Safety Rep.)
He is extremely qualified and has worked hard for his many certifications:
  • Certified Safety Professional (CSP)
  • Licensed NYC Site Safety Manager (SSM)
  • Associate Safety Professional (ASP)
  • Construction Health and Safety Technician (CHST)
  • 62 Supervisor SST Card
  • OSHA Authorized Construction Trainer
  • National Safety Council Defensive Driving Instructor
  • Construction Site Fire Safety Manager (CSFSM)
  • ATSSA Certified Flagging Instructor
  • ATSSA Certified Traffic Control Supervisor
  • 32 Hour Signal Person/Rigging Supervisor Trainer
  • 32 Hour Rigging Supervisor

Phone

845-206-7220

Samuel Hickey, CRIS

VP of Broker Relations-East Coast

Sam Hickey is the Vice President of Broker Relations at Roosevelt Road Specialty. In this pivotal role, Sam dedicates his efforts to cultivating and strengthening broker relationships across all four verticals of the organization. With an extensive background in the New York construction market and a wealth of experience in both retail and wholesale sectors, Sam brings unparalleled expertise and insight to his position.Sam is committed to delivering Roosevelt Road’s value proposition on a national scale. Through a strategic distribution model, he highlights the company’s dedication to exceptional claims handling and superior loss control services, ensuring clients receive best-in-class support and solutions.Outside of his professional endeavors, Sam enjoys traveling, golfing, and spending quality time with friends and family, balancing a dynamic career with a fulfilling personal life.

Phone

845-392-3689

Jennifer Pymm

Assoc General Counsel of Casualty

Jennifer Pymm, Esquire, is a seasoned legal professional currently serving as the Associate General Counsel at Tradesman Program Managers. Prior to this position, Jennifer served as SVP of Claims and Senior Litigation Manager.In her current role, Jennifer oversees the entire claims team, comprising both attorneys and seasoned claims executives. Her responsibilities extend to managing litigation and claims handled by Gallagher Bassett, Tradesman’s third-party administrator (TPA). She collaborates closely with defense counsel, leveraging her legal and claims background to achieve optimal outcomes in the cases under her purview. Jennifer also maintains active communication with brokers, providing updates and conducting regular claim reviews.Jennifer has over 13 years in private practice in New York and has worked for two large insurance carriers, where she developed a thorough perspective on claims, litigation, and coverage. Her supervisory role at a TPA further enhanced her skills and understanding of the intricacies involved in achieving favorable results for insured partners.Beyond her professional accomplishments, Jennifer appreciates the collaborative spirit at Tradesman, especially as the company has experienced significant growth during her three-year tenure.Jennifer is admitted to practice law in New York and holds additional admissions to the SDNY, EDNY, NDNY, the 2d Circuit, and the United States Supreme Court, highlighting her extensive legal expertise.

Phone

332-345-3716

Lily Hickey

Director of Claims

Phone

914-267-0473

Greg Mosher

CEO

Greg C. Mosher is a distinguished business and insurance executive, entrepreneur, and visionary leader with an impressive track record spanning over 40 years. Throughout his career, he has demonstrated a relentless commitment to transforming businesses and markets through a growth and value-oriented mindset.As the CEO of Renaissance Specialty Insurance Group, a managing general agency he founded in 2020, Mr. Mosher has taken the company to new heights in a short span. Specializing in insuring collegiate, amateur, and professional sports, leisure, and entertainment risks, the company achieved a remarkable $35 million in premium production within its first 12 months.Prior to founding Renaissance, Mr. Mosher served as the CEO of Specialty Insurance Group, which grew at annual rates of 35% to 45%. Under his leadership, the company generated over $215 million in profitable premium within five years of its launch.One of Mr. Mosher's most notable achievements was as the CEO of K&K Insurance Group, where he played a pivotal role in establishing the company as the world leader in sports, leisure, and entertainment insurance. Following an acquisition by Lincoln National Corporation, he also served as the CEO of Lincoln National Specialty Reinsurance Company, managing $700 million in premium for the K&K/Lincoln companies.In addition to his insurance ventures, Mr. Mosher served as the Chairman and CEO of Workflow Management, overseeing its growth from $400 million to over $1 billion in revenue in just five years. He navigated the company through major financial transactions, including privatization, mergers, acquisitions, and divestitures totaling several hundred million dollars.Mr. Mosher's diverse expertise extends to various industries, including technology, real estate, aviation, and beyond. As the founder of ITC Media Conferencing, he pioneered the world's first extensive audio and video conferencing platform for international business-to-business communications, achieving revenue growth from startup to over $250 million.Throughout his career, Mr. Mosher has exhibited a unique blend of strategic acumen, financial expertise, and a relentless drive for success, solidifying his reputation as a transformative leader in the business and insurance sectors.

Carol Ryan

Underwriting

Carol Ryan, CPCU, AU, AIS, has 30 years in the entertainment insurance industry and is VP of Underwriting at Renaissance Specialty Insurance. Carol is tasked with underwriting Sports, Leisure, and Entertainment business, mentoring Senior Underwriters, and developing new business lines and segments.  Her underwriting knowledge and understanding of Renaissance’s specialty programs and segments is unmatched. She thrives on underwriting and expanding Renaissance's business, along with training and nurturing new talent. She enjoys launching new lines of business, especially as pricing begins to soften and the entertainment segments increasingly rely on Renaissance's expertise for managing their exposures.  Carol is particularly proud of her role in fostering younger underwriters into knowledgeable and skilled professionals. She holds a degree in Biology from Long Beach State University, Long Beach, CA. A fun fact about Carol is her proficiency in Martial Arts, where she holds a 3rd-degree black belt.

Drew Ott

Marketing

Andrew Ott is the Chief Marketing Officer at Renaissance Specialty Insurance (RSI). He is a seasoned professional excelling in managing broker relationships and ensuring RSI's day-to-day commitments to brokers and insureds. With a talent for identifying and starting program opportunities, Drew has already led the development of a successful program at RSI, earning a book roll and actively working on more.What Drew values most about his role is the opportunity to closely collaborate with respected insureds in the USA, ranging from National Governing Bodies to top-tier professional sports franchises. This hands-on experience allows him to witness the intricacies of world-class operations and tailor insurance solutions to meet their diverse business needs.Drew is keenly aware of the current flight to quality with growing emphasis on expertise. Both brokers and insureds now seek carriers with a deep understanding of their specific businesses. As such, Drew ensures that RSI remains at the forefront of this trend, offering specialized knowledge and tailored solutions.Holding a BA in Management from Purdue University, Drew's also has interests Indiana University sports while enjoying mountain biking, participating in races across the United States.

Bryan Baird, RPLU

CEO

Bryan Baird, RPLU, is President & CEO of K&B Specialty Insurance (KBSI) which administers the CareAgents program through the Roosevelt Road Specialty platform. He is a seasoned insurance veteran with over two decades of proven success in business ownership, entrepreneurship, and direct sales within the senior care and residential facilities market.Prior to KBSI, Bryan successfully built the MGA platform, Lighthouse Eldercare, where he served as President & CEO. His entrepreneurial spirit led him to disrupt traditional methods of quoting and binding business insurance through the groundbreaking online platform, www.xagent.com. This revolutionary technology empowers insurance agents nationwide with unparalleled access to thousands of business lines and multiple carriers in all 50 states, enabling them to obtain bindable quotes within minutes through the innovative "Input once and submit everywhere™" approach.Energetic and driven, Bryan’s leadership is instrumental in the continued success of K&B Specialty Insurance, where he brings a dynamic leadership approach to the business. His commitment to change extends beyond insurance, as he continually seeks to revolutionize the elder care industry through innovative risk management tools and loss prevention techniques.Outside of his professional pursuits, Bryan is the proud father of six children. He is a graduate of George Mason University.

Phone

571-250-6191

Anthony Baird

Operations

Anthony Baird is the Operations Manager at K&B Specialty Insurance (KBSI) and has been with a Roosevelt Road Specialty since October 2021. For KBSI, Anthony oversees day-to-day operations, focusing on business process improvement, innovation, and IT initiatives. Anthony's unique blend of underwriting and IT skills equips him to tackle diverse organizational challenges, ensuring the underwriting and risk management teams operate efficiently. His passion for technology drives him to build and deliver solutions that simplify processes. Anthony is focused on industry trends including emphasis on automation and data analytics. Prior to joining Roosevelt Road, Anthony managed operations at an Insurtech startup and held roles at K&B Underwriters. He holds a BA in Political Philosophy from the University of Dallas. Outside work, Anthony enjoys hiking, skiing, snowboarding, and most recently, cycling.

Phone

571-250-7023

Rian Girard, CPCU

Underwriting

Rian Girard, CPCU, ARe, RPLU, serves as the Chief Underwriting Officer at KBSI. He is pivotal in ensuring the profitability and growth of CareAgents’ Senior Living book of business. Rian's extensive career includes key roles such as Chief Underwriting Officer at the Insurtech firm xagent and senior positions at notable insurers including Admiral, Zurich, and AIG. Rian thrives on the complexities and challenges that come in building a world-class organization like RRS. He is particularly focused on fostering growth in a lean and efficient manner, while simultaneously delivering unparalleled customer service. His leadership style is deeply influenced by his blend of extensive industry experience and a commitment to operational excellence. Rian holds a Bachelor of Science from the University of Notre Dame, where he distinguished himself as a member of the university's Fencing team. His sports background complements his professional drive, emphasizing strategy and precision in his approach to underwriting and business growth.

Jeff Feldman

Senior Vice President, Claims

Jeffrey Feldman is the Senior VP of Claims at KBSI and manages KBSI's claims process which includes TPA management, defense panel control, exposure assessment, reserving, and liaison work between claims and underwriting, as well as marketing assistance. Bringing over 35 years of diverse claims experience, including handling high exposure CAT claims, Jeffrey excels in swiftly assessing and strategizing on various claims to minimize exposure. A significant aspect of his role involves educating insureds and brokers about the importance of early claims investigation. With claim values escalating along with insurance fraud, Jeffrey foresees a growing significance in his role. He takes pride in his quick grasp of issues and his mentorship to younger staff. Before joining RRS, Jeffrey spent 25 years at AIG, 20 of which were in senior management in Reinsurance, Excess Claims, Healthcare Claims and Primary Construction Claims. He holds an Economics degree from Binghamton University and has a passion for “toys” including his 3-wheel motorcycle.

Phone

332-345-3745

Nick Markgjonaj

Senior Casualty Underwriter

Phone

845-820-0964

Kymbra Lier, CLCS, TCS

Associate Underwriter

Phone

914-265-9202

Al Gutierrez

VP of Broker Relations-West Coast

Al Gutierrez brings over three decades of expertise to his role as Vice President of Broker Relations for our expanding West Coast initiatives. Throughout his career, Al has held pivotal positions in both regional and national insurance agencies, as well as insurance carriers. He has a profound understanding of the commercial insurance landscape and easily navigates complex issues.Al has an unique ability to cultivate business relationships based on innovation, strategic foresight, and a commitment to excellence. This makes for “win-win-win” benefits for him, his brokers and the carriers he works with. His leadership skills, coupled with his valued expertise in underwriting, distribution, and product development, positions him as a trusted ally to brokers and carriers alike.Roosevelt Road Specialty will benefit from Al's strategic approach and adept negotiation skills as we expand our footprint across the U.S. In his role as VP of Broker Relations for the West Coast, he provides an innate understanding of the market, selfless support to our distribution partners, and the leverage that comes from our limited distribution model and cutting-edge underwriting platform.

Phone

(714) 875-1116