Paraplanner

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.

We’re Chesapeake Financial Planners—a tech-forward, boutique wealth management firm built for today’s complex clients. We provide full-service personal financial management for business owners, entrepreneurs, emerging affluent professionals, women, and retirees who want clarity, accountability, and a smarter way to manage their wealth.

We’re looking for a Paraplanner to join our small but growing team. You’ll work directly with our firm owners—one a CFP® professional and the other a CPA to prepare detailed, personalized financial plans that help clients make confident decisions about their future.

This is a behind-the-scenes role with plenty of growth potential. You’ll prepare plans, attend client meetings, and become part of a collaborative, forward-thinking team that values precision, curiosity, and continuous improvement.

• Support data gathering through PreciseFP and maintain client records in Salesforce
• Analyze financial data, cash flow, investments, insurance, and retirement scenarios
• Create clear, client-ready deliverables and reports
• Attend client meetings (virtually) to observe and, over time, explain components of plans
• Review Jump AI Notetaker meeting transcripts to help ensure accurate plan follow-ups
• Collaborate with the CFP® and CPA to refine recommendations and planning strategies

• You have 1–2 years of experience in financial planning, wealth management, or a related field
• You have a degree in business, finance, economics, accounting, or a similar field—or relevant experience in place of a degree
• You’re detail-oriented, tech-savvy, and eager to learn
• You’re pursuing or planning to pursue the CFP® designation (coursework reimbursement available)
• You’re organized, curious, and comfortable working independently in a remote environment
• You want to grow into a planner—and eventually a lead planner as the firm expands

• Compensation: Salary commensurate with experience + bonus opportunities
• Professional Development: CFP® coursework reimbursement and ongoing mentorship
• Growth Path: Clear advancement to planner and lead planner roles
• Work Environment: 100% remote, with a collaborative, supportive team culture
• Technology: Access to leading tools including Right Capital, Salesforce, Jump AI, and PreciseFP

If you’re looking for a role where your attention to detail matters, your ideas are valued, and your career path is clear, we’d love to meet you.

We’re always looking for good people who believe in clarity over confusion and people over products.