Our Team & Community

Jennifer Rose is a Managing Partner at True North Advisors, who works with individuals who want to feel informed and secure about their financial decisions as they approach retirement. She chose this career after seeing how overwhelming financial decisions can feel—and how much relief people experience when they have a clear plan and someone to keep them on track. Jen specializes in retirement income planning, with a particular focus on helping clients stay accountable to the goals that matter most to them. She helps clients turn their priorities into real-world decisions about saving, spending, and timing—so retirement feels well-planned, not unpredictable. With over 19 years of experience, Jen brings experience-backed insight and a well-rounded perspective. She holds the CLU®, ChFC®, and RICP® designations, reflecting advanced training in insurance planning, financial strategy, and retirement income. She earned her undergraduate degree and MBA from the University of Richmond. Clients often appreciate Jen’s structured, steady guidance and her ability to keep long-term plans aligned with real-life changes. She sees her role not as telling people what to do, but as helping them make informed decisions—and then following through on them. Outside of work, Jen enjoys spending time with her kids and grandkids as well as discovering great restaurants and traveling, experiences that reinforce her belief that thoughtful planning should support a life well lived, both now and in retirement.

Frankie Butler is a Managing Partner at True North Advisors in Richmond, Virginia, where he works with individuals and families who want insight and stability around the financial decisions that shape their lives. Frankie’s path into advising began with a degree in accounting, which gave him a strong technical foundation and an early appreciation for how money works. Over time, he realized he was less interested in reviewing what had already happened on a balance sheet and more motivated by helping people make better decisions about what comes next. As an advisor, he focuses on practical planning for families raising children, professionals approaching or entering retirement, and long-term investors who want their portfolios aligned with both their goals and tax situation. Clients value Frankie’s ability to translate complex financial topics into clear, actionable guidance, particularly when balancing competing priorities such as college funding, retirement income planning, and investment management. With more than 43 years of experience, he brings perspective earned across multiple market cycles and life stages, supported by his CFP®, CLU®, and RICP® designations. Frankie’s background includes years of hands-on advisory work helping clients adjust plans as careers change, families grow, and retirement draws closer. Outside the office, he enjoys exploring Richmond’s food scene, spending time on the golf course, and staying connected with family and friends—interests that reflect the same balance he helps his clients seek in their financial lives.

Russ started his career in the Financial Services industry in 1990 after attending Virginia Commonwealth University with a degree in Economics.

Russ has his Life and Health Licenses, FINRA Series 6, Series 63 and 65 registrations through Commonwealth Financial Network, and the Certified Family Business Specialist designations from the America College. Russ works with clients throughout the country and has always had a client’s first approach to his practice.

Russ is married to Lisa Cumbea and they live in Midlothian. In their free time, they enjoy traveling, visiting wineries, and playing golf. They love spending time with their 3 children and grandchildren.

Rawlings is a Financial Advisor with True North Advisors, LLC. Rawlings graduated from Roanoke College in 2017 with a Bachelor of Business Administration.

He has his Life and Health License, SIE, FINRA Series 7, Series 63, and Series 65 (through Commonwealth Financial Network). He entered the financial services industry in 2021, partnering with his Father, Russ Cumbea, in 2021 and then joining True North in 2023.

Rawlings was born and raised in Richmond. He is married to Kylie and they enjoy spending time and traveling with their son, Russell, and three dogs, Jack, Mae, and Myrtle.

Charlotte Fox is a Financial Planner at True North who helps her clients make confident, well-grounded financial decisions—especially during moments of uncertainty. She is drawn to this work because she believes financial education should be accessible to everyone, not reserved for a certain income level or life stage. Charlotte specializes in working with women and individuals navigating major transitions such as divorce, loss, career change, or sudden financial responsibility. Her approach combines empathy with actionable guidance, including thoughtful tax planning and clear, fact-based recommendations. Clients often value her ability to explain complex topics in plain language and to create a steady, judgment-free space for decision-making. With 15 years of experience in the financial services industry, Charlotte brings both profound understanding and a broad viewpoint to her work. She spent a decade at a large broker-dealer in client service roles, followed by two years working with ultra-high-net-worth families. She is a Certified Financial Planner™ professional, a credential that reflects her training and commitment to ongoing education. Outside of work, Charlotte’s favorite role is being mom to her son, Beau. She also shares her home with two goldendoodles, Louise and Myrtle. As a family, they love the beach and spending time anywhere near the water. Charlotte is deeply involved in her community. She serves as President of the Financial Planning Association of Central Virginia, is a long-time member of the Junior League of Richmond, and sits on the finance committee for Orchard House Middle School for Girls.

Payton Fackler is an Executive Assistant, Paraplanner and Marketing Coordinator who collaborates with advisors to help make the Financial Planning process clear, organized, and easy for clients to engage with. She stepped into this field because she wanted to understand the financial world more deeply—and along the way, she found how much she enjoys supporting the advisors as they help their clients make sense of their finances in a way that feels approachable and manageable. Payton assists with the behind-the-scenes work that keeps Financial plans moving forward, by communicating with clients to gather information, organizing and inputting data, and preparing analyses and reports that assists advisors with helping their clients see their options more clearly. Payton focuses on reducing complexity and giving clients the confidence of knowing that their details are being handled with care. She bring 5 years of experience that spans healthcare administration, insurance, and various administrative roles. She holds a bachelor’s degree from George Mason University and is currently studying to eventually become licensed, with the goal of expanding the ways she can support both the team and the families they serve. Outside the office, you’ll often find her spending time with her twin sister or looking for a new coffee shop or community event to explore. Her goal is simple: to take on the supporting work that allows the advisors to dedicate more time to their clients, and to help make the financial planning experience feel less overwhelming and a lot more understandable for clients, one step at a time.

Dewyonna Sites is an Executive Assistant (Investments) at True North Advisors, where she supports advisors behind the scenes to ensure clients experience smooth, accurate, and well-organized service. Dewyonna chose to enter the financial industry to gain a deeper understanding of how financial systems work and how thoughtful organization and follow-through contribute to better outcomes for clients. In her role, Dewyonna focuses on the details that keep everything moving—preparing and processing paperwork, coordinating administrative tasks, and ensuring information is accurate and complete. Her work helps advisors stay organized and responsive, giving clients confidence that nothing is overlooked. Dewyonna brings a unique and practical background that includes administrative work, tax preparation, and nursing. These roles strengthened her attention to detail, ability to work with sensitive information, and commitment to clear communication. She understands the importance of precision, follow-through, and treating each client interaction with care and respect. Outside of work, Dewyonna enjoys spending time with her family. She values reliability, trust, and strong relationships—qualities she brings to her role every day at True North Advisor. Her goal is to be a steady, dependable support for both advisors and clients, helping ensure each interaction is handled thoughtfully and efficiently.

Cathy Mask is an Executive Assistant (Insurance) at True North Advisors, and plays a key role in supporting clients as they navigate all aspects of insurance planning. With a strong background in financial planning and college funding, Cathy was drawn to the insurance space to expand her knowledge and provide more comprehensive support within the financial planning process. Cathy specializes in assisting clients with insurance applications and servicing in-force policies, while also facilitating clear and efficient communication between clients and insurance agencies. Her attention to detail and commitment to follow-through help ensure that clients feel supported, informed, and confident every step of the way. With 10 years of experience in the Insurance industry, Cathy began her career working in the legal field as a paralegal, where she developed a strong foundation in organization, documentation, and client advocacy. She later transitioned into the financial services industry, bringing those skills with her and applying them to a client-first approach centered on accuracy, responsiveness, and care. Outside of work, Cathy enjoys reading, listening to podcasts, and spending quality time with her children. She takes pride in being a reliable resource for clients as they work toward long-term financial security.