Lead Planner

At Chesapeake Financial Planners, we believe financial planning should feel clear, human, and genuinely helpful. We’re a tech-forward, fiduciary firm built on empathy, transparency, and accountability — and we’re growing a team that shares those values. Whether you’re just starting your planning career or looking to lead your own book, you’ll find opportunity, mentorship, and real impact here. All positions are remote , aligned to Eastern Time , with flexibility, collaboration, and professional development built into everything we do. Lead Planner / Lead Advisor (Remote) About Us At Chesapeake Financial Planners, we help clients cut through financial complexity with calm, clarity, and confidence. As a fiduciary firm led by CFP® and CPA professionals, we combine personal financial management oversight with accountability, using our signature R.U.D.D.E.R.™ method to keep every client on course. We serve business owners, professionals, and families navigating major transitions — with empathy, transparency, and a healthy dose of common sense. We’re a tech-forward firm using tools like RightCapital, Salesforce, Jump AI, and PreciseFP to make the planning process seamless for both clients and advisors. Our culture values collaboration, curiosity, and client-first thinking — we listen more than we talk, educate rather than sell, and believe that great advice doesn’t have to be complex. About the Role We’re looking for an experienced, client-facing Lead Planner (CFP®) who’s ready to build and manage their own relationships while contributing to a growing advisory team. You’ll serve as the primary advisor for your clients — leading discovery meetings, designing strategies, and delivering ongoing financial oversight through the R.U.D.D.E.R.™ framework. You’ll also receive firm-sourced opportunities, client hand-offs, and support from our paraplanning and marketing teams so you can focus on what you do best: guiding clients through major financial decisions with clarity and confidence. What You’ll Do Lead client relationships from discovery to implementation, acting as their trusted partner and fiduciary. Build comprehensive financial plans using RightCapital, Salesforce, and PreciseFP. Deliver proactive, tax-aware, and strategy-driven advice across investments, retirement, estate, and business planning. Collaborate with firm partners and support staff to maintain a high-touch, white-glove client experience. Participate in firm-wide growth initiatives and mentor paraplanners as the firm expands. Contribute to thought leadership and planning discussions that advance our client experience. What We’re Looking For Proven ability to manage client relationships with empathy, confidence, and clarity. Strong planning background — investment management, tax-aware strategy, retirement income, and/or business transition planning. Comfortable using technology to improve efficiency and communication. Entrepreneurial mindset with a team-first attitude. Excellent written and verbal communication skills. Growth & Opportunity If you already have existing client relationships, that’s great — we’ll help you nurture and expand them. If not, no problem. We have consistent firm-driven leads and client hand-offs ready for the right advisor who’s eager to grow within a supportive team. This position offers the ability to lead your own team as the firm continues to grow, with a path to partnership or equity for the right candidate. Salary commensurate with experience, plus performance-based incentives and bonus potential. Professional development support, including continuing education and credential reimbursement. Collaborative team environment with access to firm-generated leads and operational support. Modern tech stack and flexibility of a fully remote role. #J-18808-Ljbffr Chesapeake Financial Planners