Meet Your Team
We collectively have over 50 years of experience partnering with our clients and building long-term relationships. At the end of the day, our goal is to provide clarity and direction so that you can focus on what you care about most. In addition to serving our clients, we are passionate about developing the next generation of financial professionals to make a positive impact within our community.
Rich Jakotowicz CFA, CFP®
Director of Financial Planning
Rich is the Director of Financial Planning at Benchmark where he works with clients to ensure that there are no gaps in their plans and no surprises in their financial lives. With over 25 years of industry experience, Rich has worked with a variety of clients including entrepreneurs, executives, researchers, and teachers. Rich is knowledgeable across a range of financial issues such as investment strategies, tax minimization techniques, retirement and distribution planning, and philanthropic planning. One of the aspects Rich enjoys most is educating others on how to maximize their finances. In addition to working at Benchmark, Rich is also the Director of the Financial Planning and Wealth Management program at the University of Delaware where he teaches courses on financial planning.
After graduating from college, Rich went to work at the JP Morgan Private Bank serving clients who had invested between $10-$25 million with the bank. He worked in various roles such as Cashless Options Trader, Investment Specialist, and Wealth Manager. After 10 years at JP Morgan, Rich went to work at TIAA-CREF where he advised on the University of Delaware’s $2 billion retirement plan. After just 6 months, he was offered an opportunity to teach finance at the university. Rich has been teaching financial planning at UD (his alma mater) since 2008. He has consulted for various Investment Advisory Firms to refine their investment strategies.
Rich holds a Master’s’ degree in Finance, is a CERTIFIED FINANCIAL PLANNERTM practitioner (CFP®), and a Chartered Financial Analyst (CFA). He is the President of the CFA Society of Philadelphia, a member of the Financial Planning Association, the Society for Financial Services Professionals, and the National Association of Personal Financial Advisors. Rich also holds a certificate in Blockchain and Digital Assets from Digital Asset Council for Financial Professionals. Additionally, he serves on the Advisory Board for the St. Anthony’s Grade School in Wilmington. He is passionate about his community and educating the next generation
Rich lives in Wilmington with his wife, Ann, their two children, Richie and Andrew, and their dog, Buddy. When Rich isn’t creating financial plans, you can find him in Lewes Beach riding his bike and spending time with family and friends. He enjoys traveling, trying different food, meeting new people, and building relationships. Rich is very active at the University of Delaware.
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Jake Weaver CMFC®
Director of Investment Strategy
Jake is the Director of Investment Strategy at Benchmark where he uses a holistic approach to shape customized portfolio strategies for clients. Drawing on his 20+ years of experience in the financial planning business, Jake builds trusting relationships with clients by understanding their unique situation, helping them make significant financial decisions, and implementing the appropriate solutions. Whether Jake is serving executives, professionals, business owners, or retirees he delivers the high level of care and consistency that clients deserve while staying focused on their long-term goals. Jake manages client relationships by genuinely listening to questions, offering clear explanations, and building a personalized strategy around their goals and needs.
Jake’s background includes expertise in managing, analyzing and refining strategies for complex investment portfolios for high-net-worth individuals and families with diverse assets. Most recently, while performing in a dual role as President and Senior Investment Advisor at the registered investment advisory firm Lau Associates LLC in Greenville, Delaware, Jake drove the firm’s business vision and directed day-to-day operations while cultivating relationships with and guiding clients in making sound financial decisions. He also provided high-level insights and perspective as chairman of the Lau Board of Directors, chairman of the steering and investment committees and as a senior member of the compliance committee.
Jake holds a degree in economics from the University of Delaware and the CMFC® designation from the College for Financial Planning. Jake is a graduate of the Schwab Executive Leadership Program and is a former member of the JP Morgan National RIA Advisory Council. He is the Founder and Chairman of a national study group called The Sixth Man, which is a seven-member group of innovative and forward-thinking advisors. Jake also holds a certificate in Blockchain and Digital Assets from Digital Asset Council for Financial Professionals.
Jake resides in Glen Mills with his wife, Stacy and their two children, Brandon, and Emma. When Jake is not in the office, he enjoys spending time with his family and friends. He is an avid runner, and he also enjoys skiing and playing tennis. He loves to read, cook, and play chess as well. Jake previously served on the Financial Planning Advisory Board for the University of Delaware’s College of Business and Economics where he mentored UD students on career and personal development skills. He is passionate about giving back to the next generation of students coming through the university and making their experience at school and in the early stages of their careers more focused and meaningful.
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Caleb Ray
Financial Planner
Caleb is a financial planner and is committed to delivering comprehensive financial plans, investment analysis, and ongoing advice to support client goals. Caleb is a proud U.S. Air Force Veteran, having served for seven years as an aircraft welder, machinist, and fabricator. During his time in the Air Force, he had the distinct honor of serving on the USAF Air Demonstration Squadron, The Thunderbirds.
Following his military service, Caleb attended the University of Georgia, where he earned a degree in Financial Planning. While at UGA, he served as President of the Student Veterans Association and was a member of the Blue Key Honor Society. Caleb also participated in the Volunteer Income Tax Assistance (VITA) program where he provided free income tax preparation services to low-income families.
Caleb has successfully passed the rigorous Certified Financial Planner exam as well as the Investment Advisor exam. Caleb refined his skills as a Senior Associate at Vanguard and his expertise encompasses various aspects of financial planning. He excels in building personal connections with clients to help them achieve their unique financial objectives.
Caleb resides in southern New Jersey with his wife, Gabby, their daughter, Mackenzie, and their golden retriever, Charlie. Caleb enjoys golfing, watching the Atlanta Braves, and horseback riding.–
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Natalie Radebaugh
Financial Planning Resident
Natalie is a Financial Planning Resident at Benchmark Financial. She is a student at the University of Delaware Honors College where she is pursuing a degree in Financial Planning and Wealth Management. She is a member of the Blue Hen Investment Club where she serves as an analyst in the Financials and Real Estate sector. Natalie is also a member of Private Markets Club and Women in Finance Club where she expands her academic and career interests with like-minded individuals. In addition, Natalie brings accounting experience to Benchmark having previously done bookkeeping and tax prep work.
Natalie resides in Freeland, Maryland. When she is not in school or working, she enjoys spending time with family and friends, exercising outdoors, watching lacrosse, and boating on the Chesapeake Bay. Additionally, Natalie enjoys traveling. She has been out of the country twice and truly values meeting new people and gaining new perspectives. Natalie hopes to continue exploring new places in the upcoming years.
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Anna Goldkamp
Financial Planning Resident
Anna is a Financial Planning Resident at Benchmark Financial. She is a student at the University of Delaware where she is pursuing a degree in Finance, as well as Financial Planning and Wealth Management. Anna is involved in various clubs including the Blue Hen Investment Club, Private Markets Club, and Women in Finance Club where she continues to expand her knowledge outside of the classroom. She also works in the Geltzeiler Trading Center at the University where she assists her peers in utilizing functions available on the Bloomberg Terminal.
Anna resides in Garnet Valley, Pennsylvania. When she is not in school or working, she enjoys spending time with family and friends, reading, exercising, and playing soccer. Additionally, she enjoys traveling to new places and experiencing new cultures. She has been outside of the country twice and loves traveling south along the East Coast. Anna is looking forward to traveling with family and friends in the future.
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Strategic Partner
Jennifer Zelvin McCloskey, JD, LL.M.
Jennifer is the President of Jennifer Zelvin Law. She is available to assist Benchmark Financial clients with their estate planning needs.
Jennifer graduated from Widener University, cum laude. During law school, Jennifer was selected as one of five Wolcott Fellows, earning the opportunity to clerk for the Delaware Supreme Court under former Chief Justice Veasey.
Upon graduation, Jennifer began her career in Delaware practicing corporate bankruptcy and commercial litigation at a large national law firm. Jennifer’s career took her back to her home state of Florida in 2006, where she had the opportunity to serve her community as a criminal prosecutor for 6 years with the Florida State Attorney’s Office, 19th Judicial Circuit. In 2012, after briefly working for the Delaware Attorney General’s office, Jennifer transitioned back into private practice and began to shift her focus into trustee representation and ultimately obtaining an LL.M. in Taxation and a Certification in Estate Planning from Villanova University, Charles Widger School of Law.
In addition to dedicating her time to helping families with crafting estate plans, Jennifer shifted her practice into assisting families with trust administration at JP Morgan. In 2017, Jennifer was delighted to accept the opportunity to develop a minor course of study at the University of Delaware where she began the Lerner College Trust Management Minor. Jennifer continues to work at the University of Delaware both teaching in the Trust Management Minor and also serving as the Director of the program.
Jennifer opened her law firm to continue to help families with estate planning, and individuals with business formation. Jennifer lives in Wilmington, Delaware with her husband, her two teenage children, and two Goldendoodles.–
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