Chesapeake Financial Shares, Inc.

Administrative Associate

4804 Courthouse St., Ste 1
Customer Service/Support




Chesapeake Wealth Management


Want to work for a solid financial institution that expects 110% from its employees and rewards them accordingly? We work as a team and have high levels of engagement from our employees. A primary driver of engagement is job satisfaction. Contributors to this high level of job satisfaction are the Chesapeake benefits plan from competitive healthcare options to a generous vacation allotment. Commitment to community also plays into our job satisfaction. Chesapeake puts great emphasis on the fact that we are only as strong as the communities we serve. Therefore, we contribute dollars and hours of service to our local communities. And, we have fun doing it all!


Talk to us about a career that makes you want to get up and come to work, have fun and make a difference.





Supports CWM Relationship Manager by handling day-to-day needs for clients. Assist Relationship Manager with account management and client relations.





Specific Job Functions:    

  • Primary receptionist for CWM office in Williamsburg
  • Perform general administrative duties including maintaining client files, handling incoming and outgoing mail, answering phones and completing open/closing procedures for the office.
  • Communicate with clients: Research and solve problems, answer routine inquiries and process client requests.
  • Monitor daily account activity and confirm prior day’s transactions were processed accurately to ensure consistent client reporting.
  • Manage cash receipts and disbursements efficiently including bill payments and tax payments.
  • Work with relationship manager to ensure terms of the governing document are followed.
  • Assist assigned relationship manager with proposals and preparation of new account paperwork.
  • Establish new accounts on TrustDesk.
  • Follow and ensure opening and closing checklists are completed.
  • Provide Operations with proper transfer forms for incoming and outgoing accounts and spreadsheets for internal account to account transfers.
  • Review overdrafts and cash balances for assigned accounts and address with relationship manager as needed.
  • Assist with printing and mailing of quarterly newsletters for assigned relationship manager’s accounts.
  • Assist with marketing and planning seminars and client events.
  • Assist assigned relationship manager with referral tracking and incentive payouts for bank staff.
  • Print and bind client review books for appointments.
  • Update monthly sales and pipeline reports for assigned relationship managers.
  • Work with client’s advisors including CPAs, attorneys and insurance agents, etc.
  • Gather information and assist with client reports, tax returns and probate filings.
  • Assist relationship managers with completion of annual account reviews for Trust Committee.
  • Track and ensure all RMDs are taken prior to year end for assigned relationship manager.
  • Scanning and archiving statements and estate and legal documents.
  • Assist with new business development including planning, marketing and hosting workshops and company events, review of evaluations, gathering of information and follow through (phone calls/emails/thank you for attending letters) and scheduling of initial appointments.
  • Perform other duties as required


  • Minimum 3 + years of experience in the financial industry
  • Bachelor’s degree preferred but not required
  • Outstanding in-person communication skills and extroverted personality, as position requires dealing directly with clients and prospects of widely varying personalities
  • Computer Skills – Must be proficient in Microsoft Office, Excel, Word, and investment platforms
  • Needs to be highly detailed, organized, efficient and have the ability to work on multiple tasks simultaneously
  • Strong written skills
  • Demonstrated ability to work in a fast paced environment
  • Ability to work independently with minimal supervision
  • Strong desire to learn and problem-solving skills
  • Positive, friendly attitude and strong team player



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