Founder & Financial Advisor Tim Cummings

Originally from Scranton, Pennsylvania, Tim is the son of a teacher (his Mother, Lisa) and an insurance professional (his late Father, Timothy T.). With this background in mind, Tim started a financial advisory practice through MassMutual Pittsburgh in 2015 with a goal to educate clients and deliver advice. That practice has grown to serve clients in all ends of the country by helping those who are serious about their finances make more productive and efficient decisions with their money.

He founded Compass Rose Financial in 2020 to continue to serve his clients using a fee-based, comprehensive financial planning approach. In addition to planning and advice, Compass Rose Financial features relationships with world-class insurance carriers and investment managers to help deliver high-end solutions to its clients. By offering both standalone planning and the solutions a successful plan calls for, Tim understands financial planning through both a technical and real-world lens. Tim enjoys being actively involved in his clients’ financial lives and looks forward to the real-life benefits of their prudent financial planning. His greatest joy is to see a client retire with the peace of mind of knowing that they are prepared, buy their first house, send their children to college, or take that once-in-a-lifetime family vacation.

Based in Pittsburgh, Tim is involved in many local non-profits – as a board member, a committee chair, or as a loyal supporter. He focuses his volunteerism on causes that seek education equality, environmental protection, and affordable healthcare for children.

A graduate of the University of Pittsburgh, Tim is a lover of all things Pitt and enjoys giving back to the University whenever possible. While in school, Tim confirmed his interest in financial services via an internship with a wealth management firm in Dublin, Ireland.

Outside of the office, Tim enjoys life and its adventures with his wife, Hannah. Tim is always up for a friendly round of golf, a ski trip to the mountains, or a small-venue concert featuring a band he’s never heard of. Tim loves to travel both domestically and internationally and likes to plan vacations around the next meal and beverage. He has a deep interest in maps and geography, the basis of which is the namesake of Compass Rose Financial.


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  • Areas of Focus
  • Retirement Income Planning
    You’ve spent years turning your income into a nest egg, now how do you turn your nest egg into income? Tim earned the designation of Retirement Income Certified Professional (RICP®). He can help you build a plan to help you meet your retirement income and other financial goals throughout your nonworking years while helping you manage the many risks you may face, including long-term care planning.
  • Financial Planning for Attorneys
    Tim understands the quantitative and qualitative financial dynamics an attorney faces in life and can help you plan for them. From navigating your first offers, changing firms, starting your own practice, and eventually moving into the “retirement” phase of your legal career, Tim can provide sound financial advice so you can focus on what you do best.
  • Investment Management and Planning for Endowments & Foundations
    Prudent investment management is an important part of running a not-for-profit group, but Tim can also provide qualitative advice to your endowment or foundation to plan for the “forever” future of the organization.


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The content is developed from sources believed to be providing accurate information. The information in this material is not intended as tax or legal advice. Please consult legal or tax professionals for specific information regarding your individual situation. The opinions expressed and material provided are for general information, and should not be considered a solicitation for the purchase or sale of any security.

Securities, investment advisory and financial planning services offered through qualified registered representatives of MML Investors Services, LLC, Member SIPC.

OSJ: Six PPG Place, Suite 600 Pittsburgh, PA 15222. 412-562-4411

Compass Rose Financial is not a subsidiary or affiliate of MML Investors Services, LLC. or its affiliated companies.

Licensed to offer securities in: CO, DC, FL, GA, IN, MD, MA, MI, NJ, NY, NC, OH, PA, TX, VA, WV

Licensed to offer insurance in: DC, GA, MA, MD, MO, NJ, NY, OH, SC, TX, VA, VT