Contract and Commercial
Surety Bonds

As Senior Vice President and Chief Pricing Actuary at Roosevelt Road Specialty, Chris Donahue brings deep expertise in pricing, model development, and risk analysis across Construction and Energy segments. Prior to joining Roosevelt Road Specialty, Chris spent two decades at Arch Insurance Group, where he served as Lead Actuary for Large Accounts Construction and Subcontractor Default, managing nearly $200 million in annual net written premium with consistently strong results. He also spearheaded actuarial support for the launch of Retail Energy and Middle Market Construction, building rating models, rate filings, and segmentation strategies to improve profitability as these business units grew. Over the course of his tenure, Christopher held leadership roles across multiple lines, including High Excess Workers Compensation, Alternative Markets, Homebuilders Liability, Retail Excess, National Accounts Casualty, and Surety. Known for combining technical excellence with business acumen, Chris has a proven record of leading high-performing actuarial teams across multiple geographies and partnering with senior leadership to shape underwriting strategy, collateral management, and financial outcomes. Chris earned a B.S. in Mathematics with an Actuarial Emphasis and Business Administration from the University of Wisconsin–Stevens Point, graduating summa cum laude. He is a fellow of the Casualty Actuarial Society (FCAS) and a member of the American Academy of Actuaries (MAAA). 

Lily Hickey is the Director of Corporate Communications for Roosevelt Road Specialty and its affiliated businesses, overseeing internal and external communications, brand alignment, and strategic messaging across the organization's diverse portfolio of companies and programs. In this leadership role, Lily works closely with executive leadership and key stakeholders to ensure communications are consistent, professional, and aligned with the company's strategic objectives.

A licensed independent adjuster with the Associate in Risk Management (ARM) designation, Lily brings a strong technical insurance background to her communications leadership. Her experience in claims operations provides her with a deep understanding of insurance products, coverage issues, client service expectations, and the importance of clear, accurate, and timely communication.

Drawing on experience across multiple insurance sectors, including habitational, sports and leisure, and specialty insurance programs, Lily helps translate complex operational and industry matters into effective communications for clients, carrier partners, brokers, employees, and other stakeholders. She leads corporate communications initiatives, supports marketing and brand management efforts, and oversees company-wide messaging across all Roosevelt Road Specialty business verticals.

Lily is known for her professionalism, attention to detail, and ability to communicate complex topics in a clear and engaging manner. Her combination of insurance expertise and communications leadership helps strengthen Roosevelt Road Specialty's brand, enhance stakeholder engagement, and support the organization's continued reputation for innovation, integrity, and excellence.

Daniel Hickey Jr. has over 30 years of extensive experience across the property and casualty insurance industry. He is the founding partner and CEO of Roosevelt Road Capital Partners (RRCP), a global insurance organization that wholly owns Tradesman Program Managers, K&B Specialty Insurance, Renaissance Specialty Insurance, RISE Habitational, and Roosevelt Road Re, a dedicated MGU and Class 3B Bermuda-reinsurance company. Under his leadership, RRCP has grown premiums in excess of $1.3 billion, establishing itself as an industry leader in delivering best-in-class claims and loss control services to the construction market, real estate, sports, leisure and entertainment, and senior and assisted living sectors — all with exceptional underwriting results. Mr. Hickey served as chairman and CEO of Majestic Holdings, LLC and led the company to a successful public offering in 2005. He succeeded in turning Majestic Insurance Company, a B++ company, into an A- “AM Best”-rated company and grew premiums from $50 million to more than $150 million and expanded the business into four states. In 2016, with a visionary approach, recognizing and seizing the opportunity created by the dislocation in the New York construction market, Mr. Hickey founded Tradesman Program Managers (TPM) – a managing general agent specializing in contractors’ commercial general liability. Staffed by experts who specialize in detecting and prosecuting fraud, TPM launched a deep investigation in 2021 into fraudulent claims in the greater New York construction market uncovering a troubling pattern: staged accidents, undocumented workers filing multiple claims and suspiciously identical injury reports, all linked to coordinated efforts by plaintiff attorneys and medical providers. The initiative led to widespread legal action against predatory practices, which attracted attention from insurers around the country and from national media outlets such as the New York Post, ABC News, and Inside Edition. Mr. Hickey’s strategic insight and leadership have positioned him as a trusted authority within the industry. With a comprehensive understanding of the insurance model from top to bottom, Mr. Hickey possesses a rare ability to integrate and align key business disciplines, building and executing effective corporate strategies with precision and foresight. Mr. Hickey’s influence extends beyond business; he has an exemplary philanthropic record. He is a proud youth football coach and, for more than four decades, has hosted the Eileen Hickey Holiday Dinner on Thanksgiving and Christmas serving more than 1,500 people each holiday. Mr. Hickey received his B.A. in Business Administration from Northeastern University where he graduated cum laude.  

Rick Ecklord is the Chief Financial Officer of Roosevelt Road Specialty, bringing over 25 years of financial and investment experience to the firm since joining in 2019. Prior to Roosevelt Road Specialty, Mr. Ecklord was the President and Chief Operating Officer of Sandell Re, Ltd., a Class 3A Bermuda reinsurer, which he founded in 2014. During this time, he also established SOBC Sandell, a joint venture focused on mid-cap investments in the insurance run-off sector.Mr. Ecklord spent 19 years at Sandell Asset Management, a global event-driven hedge fund, where he served as Partner and Senior Managing Director. In that role, he led investments in the merger arbitrage space. Earlier in his career, he held equity derivatives positions at Goldman Sachs and SLK Capital Markets, and was a member of the American Stock Exchange.Mr. Ecklord earned a Bachelor of Science in Business Administration, with a concentration in Finance, from The Citadel, The Military College of South Carolina in 1995.

Tom Kelly is a seasoned attorney admitted to practice in New York State with over 35 years of legal experience. He is also admitted to the U.S. District Courts for the Southern and Northern Districts of New York, as well as the U.S. Court of Appeals for the Second Circuit.Tom brings a deep and diverse background to the company, with a primary focus on personal injury litigation, insurance coverage disputes, and regulatory compliance. He has a particular expertise in New York Labor Law claims and plays a key role in collaborating with third-party administrators and outside counsel to deliver a strong and strategic defense.Throughout his career, Tom has represented a wide range of clients, including major insurance carriers such as Main Street America, Liberty Mutual, and Lloyd’s of London. He also serves as defense counsel for multiple municipalities, including the City of Poughkeepsie Police Department, the Town of Poughkeepsie, and Dutchess County, handling personal injury and constitutional claims.Outside of his professional work, Tom is actively involved in the greater New York community, serving on several civic and nonprofit boards. He resides in the region with his wife and their three children.

Jim Kilduff is a part of Product Development at Roosevelt Road Specialty where he brings more than four decades of experience in the insurance industry with a strong focus on program development, underwriting strategy, and carrier relations. Known for his deep market knowledge and collaborative approach, Jim plays a critical role in driving growth and success of Roosevelt Road Specialty's insurance offerings.Throughout his career, Jim has built a reputation for developing innovative, client-focused solutions tailored to niche industries and emerging risks. His ability to align underwriting performance with strategic goals has earned him the trust of brokers, MGAs, and carrier partners alike. At Roosevelt Road Specialty, Jim is instrumental in structuring and managing programs that deliver both profitability and long-term value to insureds.Jim's leadership is grounded in integrity, responsiveness, and a genuine commitment to build strong, sustainable partnerships across all areas of the insurance value chain. His experience spans both the retail and program sides of the business, giving him a comprehensive perspective that informs every aspect of his work.As Roosevelt Road Specialty continues to grow, Jim remains focused on delivering underwriting excellence, operational efficiency, and outstanding service to clients around the globe.

Greg Jablonsky has served as Chief Information Officer of Roosevelt Road Specialty since 2021, overseeing IT strategy and operations across all subsidiaries, including Roosevelt Road Reinsurance. Known for his strong communication skills and active listening, Greg brings a collaborative approach that bridges technology with business objectives.He works closely with cross-functional teams and frequently partners with the CFO on actuarial analyses, contributing a fresh perspective that enhances organizational efficiency. One of the key challenges he navigates is aligning stakeholder expectations with the time-intensive demands of IT projects—an area where his clarity and foresight are essential.With more than eight years of experience as a CIO, Greg has held leadership roles at the New York Power Authority and IBM. He earned a Bachelor of Science in Information Systems from Pace University and continues to embrace a forward-thinking “What’s Next” mindset in his professional growth.