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.

TRACEY A. CARRAGHER > Chief Executive Officer

Fearless. Passionate. Collaborative.

Tracey sets a powerful vision for constant service improvement in every aspect of the business of insurance distribution. If there is an opportunity to enhance the experience and outcome for a client, she will inspire, motivate and encourage her team to find it, elevate it and set it forward. Her role as CEO and founder of Breckenridge Insurance Group is to make sure the organization continues to realize new opportunities by innovating and delivering smart, achievable solutions.

Tracey’s exceptional career began at General Re and McKinsey, and she went on to hold top jobs at Frank B. Hall and Alexander & Alexander before she became part of the senior management team reporting to the president at Aon. Tracey was involved heavily in steering strategic decisions of Aon’s E&S businesses spanning multiple wholesale, MGU, alternative risk and consulting practices globally. When Aon sold its investment in Cambridge Integrated Services Group, Tracey agreed to stay as CEO, transforming the company into the largest third-party administrator in the country. With her experience across the entire insurance transaction chain, she identified the need for a better, more efficient, customer-centric operation and the idea for Breckenridge emerged. The company fully launched in 2009 with a carefully selected team of coveted industry leaders, investors and an acquisition.

In recognition of her many accomplishments – particularly as a champion of diversity in the industry having funded research on this topic—Tracey was named the 2015 Insurance Woman of the Year by the Association of Professional Insurance Women. She is a 2017 Insurance Business America Hot 100 honoree and recently presented at the Insurance Business America Women’s Summit in Chicago on Breaking the Glass Ceiling. She has also presented at numerous conferences, been quoted as an industry expert, and has mentored several professionals. Her generous support of many non-profits, including the Station Foundation for veterans and several children’s organizations and pet rescue services, benefit the greater community.

tcarragher@breckgrp.com  855-728-8822

Joseph P. Filardo CPCU, ARM > SVP, Property & Casualty

Inquisitive. Good-Natured. Proven.

Joe is an experienced insurance professional who provides strategic guidance in business development both on the carrier and client side. His vast knowledge of the program insurance business and expert analytic skills coupled with his marketing and sales background allow him to look at opportunities for both their risk soundness and growth potential. Having been a founding partner in Breckenridge in 2009 and starting our  Blue River Underwriters division in 2010, he returned in 2018 as a valued leader and driver familiar with our distribution appetite. Prior to Breckenridge, Joe founded a risk management consultancy, was President of Pacific Wholesale Brokers, CEO of Aon Specialty Re and a Production and Marketing Director at Cooper Gay. Joe has an interesting combination of degrees from Fordham University – that of BS in mathematics and philosophy. He currently resides in Portland, Oregon and enjoys reading, working out and is an avid baseball fan.


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.

kstephens@breckgrp.com  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.

cmitchell@breckgrp.com  678-631-5961

FRANK CARRAGHER > Chief Enterprise Solutions Officer

Persevering. Analytical. Personable.

As Chief Enterprise Solutions Officer, Frank oversees process enhancement strategies to increase productivity and value for clients. His analytic and experienced perspective is helping to evolve best practices and identify complementary global partnerships that deliver measurable results. Previously, Frank was Vice President of Vendor Management and Operations at Loan Protector Insurance Services, a Willis company. He was also Vice President of Global Sourcing/ Business Performance Outsourcing Manager for PNC Bank and held senior vendor management positions for Cambridge Solutions LTD (now part of Sedgwick Claims Management Services) and Ohio Savings Bank. Frank has a B.A. from the University of Michigan and an M.B.A. from Case Western Reserve University. He is an avid tennis player and enjoys travelling and cheering on the Wolverines at “the big house” with his wife.

fcarragher@breckgrp.com  330-302-0023

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.

acruz@breckgrp.com  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.

james@oscis.com  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.

kgilroy@oscis.com  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.

jperez@oscis.com  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.

mrandall@oscis.com  803-237-5428

Stephen J. Kelley > President, Blue River Underwriters

Responsive. Knowledgeable. Steady.

Steve has built his impressive 30-year insurance career in the commercial underwriting space. Steve most recently was with SeaBright Insurance Company, leading nationwide business development field operations. Previously, he was at Aon Corporation as President of Muirfield Underwriters with premium writings exceeding $1 billion under his tenure. Additionally, he has held key management positions at AmTrust North America and Casualty Insurance Company. Steve oversees Blue River underwriting programs and facilities with a focus on divisional growth, program quality, and partner value. He also is charged with product enhancement and the development of new programs. Steve enjoys spending time with his wife Cathy and five children and playing golf. He is also very passionate supporter and past President of the Board of Directors of The Cancer Support Center, a non-profit in the Chicago area.

skelley@blueriveruw.com  312-521-8966

Robert J. Matamoros, CPA > EVP, Specialized Distribution

Perceptive. Resourceful. Inclusive.

Bob has 15 years of financial and operational leadership experience in the Surplus and Excess Lines industry. At Breckenridge, he is charged with optimization of distribution across the group to best target opportunities for our diverse specialty offerings. Previously, he served as EVP of the brokerage and contract binding division having overseen team production as well as involved in business development and carrier relations. Previously, Bob held CFO roles at both Regional Excess Underwriters (REU) since 2013 and before that, 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 “orangeblood” enjoying all Longhorn sports.

rmatamoros@breckgrp.com  877-738-8166

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.

ray.scotto@targetmkts.com  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).

somalley@breckgrp.com  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.

CHENRY@BRECKGRP.COM   267-961-8252