Jeffrey Levy, LACP

Principal & CEO

C: 410-916-9777  O: 410-517-1592 ext 105

With almost four decades in the life insurance industry, Jeff Levy has built his reputation on finding paths where others see walls. He is known for his creativity, ingenuity, and knowledge – the foundation which allows him to guide your complex and intricate cases from idea to implementation. Jeff has held senior sales positions with Phoenix Mutual and Highland Capital before founding Chesapeake Brokerage in 2011.

As the driving force behind Chesapeake Brokerage, a new aged firm with old school principals, Jeff knows what truly drives clients and their advisors. As an advisor you build your clients financial plan by connecting with them and understanding their needs, wants and goals.  Once you are there your recommendations follow suit. At Chesapeake Brokerage we take the same approach to advising you through the complex and often confusing world of insurance.

Jeff is a member of the BEPC (Baltimore Estate Planning Council), AALU (Association for Advanced Life Underwriting) and NAIFA (National Association of Insurance and Financial Advisors).

Although Jeff has been recognized with countless awards throughout his career, his greatest awards come through his family. Jeff and Marge have been married for 32 years and are not only partners in life, they are also business partners. Together they have three wonderful daughters, Megan, Amanda and Samantha. Born on Miami Beach Jeff is a diehard Dolphins fan. He lives in Finksburg, MD, enjoys playing golf, hiking, fishing, traveling and collecting rum.

Marge Levy

Director of Contracting & Licensing

410-517-1592 ext 102

Marge Levy has over 18 years of insurance industry experience in the areas of Contracting, Underwriting, New Business, Group Pensions and Group Benefits. She is responsible for Contracting and Licensing for Chesapeake Brokerage.

With strong organizational and communication skills, you’re ensured that your contracting experience will be a pleasant and smooth one. Marge’s expertise, knowledge, and “hands on” style continues to emphasize Chesapeake’s “Human Factor”.

Marge is a native of Northeast Philadelphia and now lives in Finksburg, MD. When she is not working, Marge enjoys spending time with her husband Jeff and her three daughters. She enjoys the outdoors, hiking, traveling and has a passion for interior designing and decorating.

Linda Bennett, FLMI, ARA

Director of New Business

410-517-1592 ext. 101

Linda Bennett started her insurance career in 1999 as a new business processor for a large brokerage firm in Maryland. She joined forces working with Jeffrey Levy in 2007 at Highland Capitol,leading the new business team for the MD/NOVA/DC markets. Linda was named Director of Underwriting and New Business, upon the foundation of Chesapeake Brokerage in 2011.

In addition to underwriting and new business Linda works closely with Licensing and Contracting. Her experience gives her great insight in accessing your client’s underwriting situation. Linda maintains close relationships with carrier underwriters, as well as, Chesapeake Brokerage’s in-house underwriters, to give her an advantage when getting tough cases approved. She is very detailed oriented and takes pride in her work. She will assist you and your team with presenting your clients to our carriers in their best possible light.

Linda has her FLMI, ARA, and has been recognized for her work with Life Office Management Association from the Association for Advanced Life Underwriting.

Linda lives in Gettysburg, PA with her husband, Tom and enjoys reading, working out, hiking, biking and dog training.

Evan Roberts

Brokerage Vice President

 C: 443-465-5548 O: 410-517-1592 ext 103

After being with Chesapeake Brokerage for almost 10 years, Evan Roberts is a firm believer that the team at CB is the difference! He started as an internal marketer and sales support in 2012 and became Brokerage Vice President in 2015. His primary responsibilities are in assisting and partnering with producers to grow their client base through creating relationships and sharing his marketplace knowledge. Evan brings a unique passion to every opportunity and challenge. His competitive spirit drives him to immediately seize every opportunity with the overall desire to surpass his client’s goals and experiences.

Evan is a practitioner of the strategic planning involving life insurance, annuity, and long-term care products, and uses this experience to bring you closer to your client, build a trusted relationship, and provide the best experience he can. Through his exploratory process, he provides effective and efficient paths to capitalize on business opportunities, and grow his relationships. By actively partnering in your practice and providing a hands on approach to case design, sales ideas, and underwriting you are assured a comprehensive solution to helping your clients and building deeper relationship with them.

Evan is active both civically and in the industry. He is a Board Member of NAIFA Baltimore’s Young Advisors. He is a graduate of McDaniel College, where he played lacrosse.

Evan lives in Annapolis MD with his wife Saralyn, their son Holden, and Ralph the dog. He is a golf enthusiast and Penn State fan. He enjoys playing basketball, going to concerts, and staying active.

Kevin R. Beck, CFP®

Design Analyst

410-517-1592 ext. 107

Kevin Beck has been with Chesapeake Brokerage/in the insurance industry for three years. His primary responsibilities with Chesapeake Brokerage are as a Design Analyst. He also he provides case consultation, product due diligence, illustrations support and preparation of presentation materials. He is available to answer product or carrier questions, as well as, existing coverage questions/ analysis, and to help advisors with their business. A graduate of the Marriott School of Management, at Brigham Young University, with a degree in Finance, Kevin brings both technical training and an analytical nature to bear in solving problems.

Kevin’s vast experience with top tier firms makes him an asset to Chesapeake Brokerage. Prior to CB, he has worked as an advanced markets consultant at the carrier level, at the brokerage level for a wholesale insurance product outlet, and with a high end advisory firm, with a reputation built on thorough, outside-the-box guidance for business owners and their key employees. Kevin understands life insurance and is skillful at using carrier illustration software. His insurance capability encompasses business insurance and executive benefits, including guaranteed issue alternatives. He has practical experience with disability income insurance and long term care insurance options. 

Outside of work, Kevin is very active in the community and in his church. He has volunteered as a leader in Boy Scouts and as an Eagle Scout mentor. For five years he had oversight of the disbursement of a charitable organization’s budget for assistance to those in need of housing and food. He met with those seeking assistance to determine needs, and developed plans to help them become more self-reliant.

Kevin has been happily married for more than thirty years. He and his wife have five children, one goofy dog, and seem to be supporting, from their garden, a sizable den of rabbits and small herd of deer. He loves reading, a wide variety of music, sports, and horse riding.

Jared Rosen

Sales Associate

410-517-1592 ext. 109

Jared began his career in financial services and life insurance in 2004 with Mass Mutual.  During his time there, Jared focused his time working with families with a special needs situation and earned the Mass Mutual designation of Special Care Planner.   In 2012 Jared joined a National firm specializing in Executive Benefit Planning. In this capacity, he worked directly with businesses on their non-qualified deferred compensation, BOLI/COLI, split dollar and Section 162 plans. 

Having a desire to return to individual planning, Jared joined Chesapeake Brokerage in 2019 as a Sales Associate, building out the Washington, DC region. He is responsible for working with insurance advisors, wealth managers, and financial planners to help design and implement insurance solutions. 

Leveraging his experience in both the individual planning with a mutual carrier company and working with high-net-worth individuals and business owners in the executive benefits space, Jared will bring a wealth of knowledge and ideas to Chesapeake’s Advisors. 

Jared was born and raised in Montgomery County, MD, and currently resides in Kensington with his wife Stephanie and daughter Eliana.  In his free time, Jared enjoys supporting the local sports teams he grew up with, including the Washington Football Team, Washington Capitals, and Baltimore Orioles.  During football season, Jared helps to host a 200-person tailgate at FedEx Field. 

Adrienne Blankenship, FLMI

New Business Administrator

410-517-1592 ext. 106

Adrienne Blankenship has been in the insurance industry for 25 years and has gained experience in various roles including: Business Analyst, Operations Analyst, Trainer, Technical Support Rep, Client Onboarding Specialist, and Customer Service Representative. As a new business administrator for Chesapeake Brokerage, she will strive to make sure that you obtain the best offer for your client with communication and efficiency.

She started at First Colony Life/GE Life & Annuity as a New Business Case Manager where she achieved her FLMI designation. She has since worked with an Employee Benefits Broker, Piedmont Community Health Plan, and Ebix CRM. During her tenure with Ebix, she served a variety of clients across the world to ensure they were up to speed with maintaining and tracking their business.

Adrienne is customer service minded and will always strive to make sure the customer has what they need to be efficient and productive. She looks at the experience as if she were the customer to determine how she would expect to be treated.

Originally from South Jersey, Adrienne moved to Virginia after college where she currently lives with her husband and boy/girl twins. Together they enjoy supporting their children in their many extra-curricular activities and camping with family and friends.