Choosing the right business partner makes all of the difference. Turn to an experienced team that prides itself on building long-term relationships and delivering exceptional, value-driven service at every step. At Breckenridge Insurance Group, we hire proven professionals and give them the support they need to deliver results. As passionate, industry-leading experts in our respective fields, we are confident you will gain new and ongoing insights throughout our relationship. You will also rest easier when it comes time to implement with our deep bench of talent across the organization. We want to be the partner you covet.

DAVID JORDAN > President and CEO

Disciplined. Inspiring. A Good Person.

As in his prior roles and now as head of the Breckenridge Insurance Group, David is a champion of clients’ interests and in empowering the team to anticipate and excel in serving their needs. With nearly 40 years of property and casualty insurance industry expertise, he’s helped build several companies into trusted and respected leaders by way of discipline, transparency and collaboration. Before Breckenridge, David was with Vela Insurance of W.R. Berkley Corporation for a decade as President and CEO. There he grew the company significantly having tremendous success in addressing market needs with new products and an unwavering commitment to client service excellence. He additionally served in leadership roles as COO of Risk Specialists Companies and Senior Vice President of Lexington Insurance Company and a Vice President at both AIG and Atlantic Mutual Companies. As newly appointed to the helm of Breckenridge, David is looking to build on the firm foundation of the company now celebrating its tenth year of operation. He is enthusiastic about the opportunity to harness the entrepreneurial spirit and drive of the talented team within and preserve the innovative Breckenridge culture backed by strong financial investment and led by a proven management team. In his free time David can be found cooking and traveling, or both.

Tel: 678-322-3535

Kirk Stephens, CRCM > Chief Compliance Officer

Experienced. Informed. Integrity.

As Chief Compliance Officer of Breckenridge Insurance Group, Kirk spearheads our industry-leading compliance practices. In this role, he manages the implementation of sound compliance practices and oversees corporate governance best practices. In addition, Kirk provides financial risk management advisory and compliance services to banks and other mortgage lender clients of OSC. Kirk is a 20-year veteran of the Federal Deposit Insurance Corp. (FDIC), where he most recently provided strategic direction and advice on supervisory examinations and oversaw and managed the operations for the Senior Deputy Director of Supervisory Examinations in Washington, D.C. Previously, he was a regional FDIC case manager, directing the risk management examinations of financial institutions with $20M to $140B in assets. He began his career at the FDIC as a federal bank examiner. Kirk regularly contributes to national publications as well as speaks at national conferences on compliance-related issues as well as publishes a well-regarded lender compliance newsletter.

Tel: 678-322-3521

Chris Mitchell > Chief Technology Officer

Results-Oriented. Collaborator. Considerate.

As head of technology for Breckenridge Insurance Group, Chris is charged with all technology oversight including infrastructure, systems, proprietary products and support. He works closely with the heads of varied companies, internal department heads, external vendors and international carrier partners to implement strategic company priorities. Chris has more than 17 years of insurance technology experience. Most recently he was chief information officer of Swett & Crawford and prior to that he was a senior vice president of information technology at Aon Services Group where he served in variety of IT roles with subsidiaries of St. Paul Fire and Marine’s facultative and treaty units. When not guiding the technology team, Chris enjoys spending time with his wife of 31 years and his daughter, who recently began her legal career in Atlanta. They are active in their church and local community groups.

Tel: 678-631-5961

Angel Cruz > SVP, Finance

Expert. Charismatic. Thoughtful.

Angel is responsible for financial best practices, leadership, reporting, and analyses across Breckenridge Insurance Group as SVP, Finance. He provides strategic fiscal guidance as a member of the senior management team working closely with the leaders of all divisions and corporate departments. Prior to Breckenridge, Angel was director of financial reporting at Swett & Crawford where he spent nearly 14 years. Angel has an additional 11 years of accounting experience in insurance and other industries from investments to manufacturing to banking for varied divisions of American Financial Group including Infinity Insurance and Atlanta Casualty and Windsor Group (now Infinity). Early in his career, Angel worked for National Service Industries and began his career at the Federal Reserve Bank of Atlanta. He enjoys spending time with his family, traveling and playing golf.

Tel: 678-460-3213

JAMES ROBERTSON > Executive Vice President/OSC

Experienced. Astute. Gracious.

As Executive Vice President, James is heavily involved with business development at OSC. With his experience building successful companies, he consults on operations and strategic initiatives related to excess & surplus lines programs and directors and officers liability insurance for public entities, attorneys, small capitalized companies, and the financial services sector. Previously, James served as Managing Director of Aon’s Cambridge Integrated Services Group, and served as CEO of CARE Systems Corporation, a software development and casualty claims company acquired by Aon. Prior to that, James co-founded Medical Intercept Systems, which ultimately merged with Physicians Support Systems. His early days were spent successfully growing RIA, a commercial insurance brokerage, which he later sold. Although he thrives on working with fast-paced, growth-oriented companies, James enjoys the leisurely pace of golf in his free time.

Tel: 469-320-4050

Keith J. Gilroy, C.P.A. > President, OSC

Proactive. Dedicated. Attentive.

Keith is at the helm of OSC having proven his contributions to the organization as VP of the Breckenridge finance department. His more than 20 years in the insurance and financial services industry gives him a great foundation for the leadership of OSC and appreciation for the needs of its clients and his internal team. As President, Keith oversees all aspects of business and operations of the technology- and compliance-driven organization and is charged with bringing new products and services to the market. Most recently, Keith was the controller at one of the nation’s largest insurance wholesalers Swett & Crawford. Prior to Swett, he was CFO of Aon Specialty Re and held several senior leadership positions at CV Starr agency companies. Keith is a graduate of Pace University with a BBA in accounting and holds his CPA and Property & Casualty license in the state of Georgia. When not driving growth, Keith enjoys spending time and traveling with his wife and children as well as the occasional round of golf.

Tel:  678-460-3235

José Perez de Corcho > Executive Vice President/OSC

Savvy. Supportive. Engaging.

José is a vital leader within OSC as he oversees client services while also involved in building key relationship with carriers and prospective clients. He joined OSC when his company—Financial Insurance Brokers, Inc.—merged with Overby-Seawell in 2009. His insurance career started in 1990 at AIB Financial Group in South Florida. In 1994, José joined Smartrack Financial Services, where he focused on developing real estate insurance tracking & placement programs and a Point of Sale, Physical Damage program for automobile finance companies. José holds a Marketing and International Business degree from Florida International University, where he is on the Alumni Board of Directors. He is an active member of the South Florida Hispanic Chamber of Commerce, the National Automotive Finance Association (NAF), and the American Financial Services Association (AFSA). Outside of work, José enjoys spending time with his family and pursuing his passion for wine.

Tel: 305-510-9267

Michael Randall > EVP, Director of Business Development

Knowledgeable. Energetic. Well-Liked.

Michael has more than 20 years of experience providing insurance solutions to the financial industry having worked closely with loan operations, compliance and risk management teams, as well as agents and brokers. As EVP, Director of Business Development, Michael will lead all OSC new business initiatives and work across Breckenridge Insurance Group to deliver innovative risk management solutions to clients. Prior to OSC, Michael spent a decade working in the Property & Casualty business as an operations consultant to banks, mortgage servicers, and credit unions. Early in his career at AIG, he was integral to cross-selling initiatives for life insurance and credit insurance programs. Michael is a graduate of the University of South Carolina with a degree in Economics and resides in Columbia, SC. He enjoys travel and spending time with his wife and two daughters.

Tel:  803-237-5428

Tim Anders, CPCU > Senior Vice President, Underwriting

Strategic. Practiced. Personable..

Tim Anders is responsible for managing the technical underwriting aspects of Breckenridge Insurance Services Contract Binding and Blue River Underwriters Programs. This includes overseeing new product development, developing and implementing best practices, and managing underwriting strategy and communications across divisions. Tim was most recently VP, Underwriting and Operations for GuideOne Insurance and previously was VP for Alternative and New Programs at Zurich North America. He has also worked in senior roles at The Hartford and Atlantic Mutual Companies.


Trevor Pierce > President, Breckenridge Insurance Services

Personable. Collaborator. Experienced.

Trevor leads the Brokerage & Binding team at Breckenridge Insurance Services. As a former retail agent with nearly 20 years of experience, he helps clients and team members realize greater success with his diverse experience with top-rated carriers and a competitive, service-minded approach. He is integral in identifying and empowering talent across our group, collaborating on key product offerings, and increasing production with sound risk management practices. Trevor has a Business Degree from Southwestern University. He enjoys spending time with his family and is an avid golfer as well as skier, snowboarder and mountain biker.

Tel:  469-320-4038


Dennis DiCapua > President, Blue River Underwriters

Welcoming. Accomplished. Driven.

Dennis has a demonstrated track record of building increasingly successful program and specialty businesses throughout his 40-year insurance career. As head of programs for Breckenridge, he is focused on driving continued program growth by way of new offerings, coverage enhancements, strategic hires, and advanced technologies to support agent, carrier and team success. Prior to Breckenridge, Dennis founded a managing general agency, Newport General Agency, that was sold to AmWINS in 2010. He then served as the executive vice president and chief risk officer of the AmWINS Specialty Auto company, where he assisted with the consolidation of newly acquired companies, enhanced carrier and reinsurer relations and launched innovative mobile technology solutions. He also served as senior vice president of specialty programs at Clarendon Insurance Group and managed a P&C portfolio of more than $500 million in gross written premium. His early career focused on building the non-standard auto businesses at Reliance National Risk Specialists and American International Group. Dennis works in our Dallas-area office and, outside of work, enjoys spending time with his wife, Helen, and his son, Nick, who recently began his finance career in NYC.  Dennis is also a third baseman and catcher for a nationally-ranked amateur baseball team.

Tel: 469-472-1477

Robert J. Matamoros, CPA > President, Southeastern Underwriters, Inc.

Perceptive. Resourceful. Inclusive.

Bob oversees Southeastern Underwriters in providing longstanding lender-placed insurance expertise to community banks. Previously, he led optimization of distribution across Breckenridge Insurance Group to best target opportunities for our diverse specialty offerings. Before that, he served as EVP of our wholesale brokerage and contract binding division where he led team production and was heavily involved in business development and carrier relations. Additionally, Bob held CFO roles at both Regional Excess Underwriters (REU) and served as CFO of Colemont Corporation. He graduated with a BBA in Accounting from The Red McCombs School of Business at The University of Texas at Austin. Bob enjoys traveling with his wife and children and considers himself is a true “orange blood” enjoying all Longhorn sports.

Tel:  (804) 550-2376 X4113

Ray Scotto > Executive Director/Target Markets

Diligent. Connected. Amicable.

For over a decade, Ray has been instrumental in the Program Administrators industry as Executive Director of Target Markets. His efforts have realized greater membership, collaboration, and business success for participants with the help of a dedicated team of professionals and the support of valued board members. Ray was instrumental in the development and implementation of several Association initiatives including the commercial website, Target Programs, the Program Administrator Best Practice Designation, Target University, and TMPAA Charities. Prior to Target Markets, Ray served as the administrator of a child abuse investigation unit in southeast Pennsylvania for 22 years. He has also worked as an adjunct professor at West Chester University in Pennsylvania. Ray holds a Master’s degree in Social Work. Outside of work, Ray enjoys sailing with his wife.

Tel: 302-268-1010

Sonya O’Malley, SPHR, SHRM-SCP, CEBS > VP, Human Resources

Skilled. Open-Minded. Friendly.

As head of human resources, Sonya leads all aspects of talent recruitment, organizational development, employee policies, payroll and benefits of the growing Breckenridge team. With more than 20 years of human resources experience in the insurance industry, she offers sound guidance in a familiar industry as well as new ideas as part of a progressive company. Previously, Sonya was AVP of Human Resources for Regional Excess Underwriters (REU). Prior to joining REU, Sonya was Director of Human Resources for Acadia insurance.  Sonya is a credentialed HR professional, earning the Senior Professional in Human Resources (SPHR) designation in 2004 and the Certified Employee Benefits Specialist (CEBS) designation in 2003.  She holds a bachelor’s degree in business administration from Husson College in Maine. In her spare time, Sonya enjoys traveling with her husband, spending time with friends and family, and shopping (mostly for shoes).

Tel:  866-796-7890

Caren Henry > VP, Marketing

Knowing. Creative. Outgoing.

Caren heads up the public relations, integrated marketing and internal communications efforts of the dynamic Breckenridge Insurance Group. With 22 years of marketing high-growth companies across a variety of industries, she brings an experienced and new perspective to the team. She leads brand development, conceptual/message development and marketing planning and implementation for Breckenridge products, services and technologies. Caren previously ran her own virtual ad agency having built successful ad agencies for others including GSW Worldwide and inChord Communications (now inVentiv Health). She grew up in Columbus, Ohio and is a University of Michigan graduate and Big 10 Championship swim team member. She now enjoys USTA competitive tennis, hanging out with her husband, and spoiling their three rescued dogs and two cats.

Tel:   267-961-8252