Town Administrator

Town of St. Michaels, MD | Full-time


The Position

The Town of St. Michaels is seeking a Town Administrator who will provide exceptional services, modernize Town processes and systems, and help the Town define its future by building on its current architectural, historical, and natural coastal beauty. Named as one of the Top 10 Best Small Coastal Towns in America by USA Today, the Town is a tourist destination offering exceptional shopping, restaurants, lodging facilities, and outdoor activities. A mix of full-time and part-time residents have been attracted by the Town’s beauty and its colonial village history, which provides a quiet haven in a beautiful setting, yet close to major metro areas of Baltimore, Maryland, Washington, DC, and Philadelphia, Pennsylvania.

As the Town’s chief administrative officer, the Town Administrator runs the day-to-day operations and oversees Town staff. The Administrator develops and recommends the annual operating budget, enforces the Town Code, and implements the Commissioners’ policies and decisions. The Town Administrator leads a talented and dedicated team of six direct reports, including the Police Chief, Finance and Human Resources Clerk, Director of Public Works, Town Clerk, Communications Manager, and Planner. The Town Administrator reports to the Town Commissioners and attends all Commission meetings.


  • Build strong, positive relationships with the Town Commissioners. Establish clear expectations, provide clarity around roles, and ensure consistent and transparent communication throughout the organization.
  • Take the necessary time to learn and understand the St. Michaels community. Build connections, support engagement, and ensure the Town is connected to the community at all levels. Assess organizational structures, challenges, and areas for improvement. Work with the Town Commissioners to suggest improvements and make recommendations for implementation.
  • Oversee key priorities of the Town that are underway, which include:
    • Working with Maryland State Highway Administration on the completion of the Talbot Street (Route 33) sidewalk project
    • Identifying location and funding strategy for Town Hall and Police Station
    • Implementing a new remote water meter reading technology
    • Supporting the shift to a new outsourced trash and recycling provider
    • Improving the Town website, online customer services, and communications

The Successful Candidate

The next Town Administrator is a skilled professional dedicated to local government service, who will assist the Commissioners in developing strategic Town goals, execute the priorities of the Commissioners, oversee the daily operations of the Town and staff, complete special projects, and develop and administer the annual budget. The successful candidate will be able to help the Commissioners come to a consensus and help balance the preservation of the Town’s rich history with the promotion of economic growth and the infrastructure to sustain it. The successful candidate will be a person that helps the Commissioners establish both short- and long-term goals, promote economic resiliency, and identify opportunities to improve its services to residents and businesses.

The ideal candidate will be knowledgeable of state, county, and local government and will provide strong leadership around accountability, transparency, and rules and regulations. With a successful track record with change management, the next Town Administrator seeks to use data to drive decision-making that encourages the appropriate balance of economic growth for the community.

The next Town Administrator will establish effective working relationships with elected officials, Town staff and contractors, businesses, residents, and volunteers. The model candidate will also provide excellent customer service to the residents of St. Michaels, both directly and indirectly, through their leadership of the staff and oversight of the various services provided. The successful candidate will be able to balance and prioritize numerous concurrent responsibilities. The Town Administrator is a poised communicator who is both politically savvy and politically neutral and provides a strong voice for the Town's best interest.


Minimum requirements include any combination of education and experience equivalent to a bachelor’s degree in Business, Public Administration, Engineering, or related field. A minimum of five (5) years of local government management or equivalent experience is required.

Preferred qualifications include a master’s degree in Business, Public Administration, Public Policy, or a closely related field. An ICMA Credentialed Manager is preferred. Experience working in a coastal and/or tourism destination, modernizing Town policies and practices, pursuing and writing grant applications, and working in a small town with high customer expectations is also preferred.

Residency is not required. The successful candidate should reside in a proximity to the Town that enables the Administrator to respond to emergencies in a timely manner. This is not a virtual position.

Inside The Town of St. Michaels

The Town of St. Michaels operates under the commissioner form of government, in which an elected body appoints a Town Administrator to oversee the day-to-day operations of the municipality. The Town Commissioners consist of five members, all of whom are elected to serve staggered two-year terms. The St. Michaels fiscal year 2022 approved operating budget includes a General Fund of $3.42 Million and a Water Fund of $800,000; the Town employs 23 full-time employee. Services provided by the Town include Public Works, Police Department, Planning and Zoning Department, parks, harbor, and refuse and recycling.


The Town of St. Michaels continues to be a vibrant and livable community preserving the Town's strong historic character and long-standing waterfront orientation. We will protect our small-town quality of life and promote environmental stewardship and economic vitality. We value opportunities in housing diversity, arts and culture, connectivity, walkability, and transportation options.

Core Values

  • Respect: The best quality of life will be achieved when the needs of all its citizens, business owners, taxpayers, and other stakeholders are respected and considered.
  • Integrity: Demonstrate honesty and sincerity in all cases, upholding only the highest ethical principles; to provide open and transparent communications to create an informed opinion.
  • Compassion: Sensitivity to and meeting the requirements of all residents and businesses with special needs and interests, and those less fortunate.
  • Fiscal Responsibility: Elected officials, appointees, and staff are always mindful of the need to balance town services with reasonable fiscal responsibility.
  • Community Involvement: Achieve the best quality of life for all citizens by ensuring business owners, taxpayers, and other stakeholders are actively engaged in the Town's decision-making and work cooperatively to achieve the overall goals as set forth herein.
  • Innovation and Imagination: Seek innovative and imaginative ways to address the future while maintaining the historic character of the Town.

The Community

St. Michaels is the most prominent tourist town in Talbot County. The Town is home to the Chesapeake Bay Maritime Museum, where you can immerse yourself in maritime history. The St. Michaels area is perfect for outdoor activities, including boating, kayaking, golfing, and bicycling. St. Michaels is also known for exceptional inns and lodges, quaint romantic bistros, waterfront restaurants, fresh seafood, and the best tasting crab cakes. Shoppers will find an eclectic range of boutique shops offering specialty foods, jewelry, clothing, home decor, and art galleries throughout the Town.

St. Michaels appeals to residents desiring to put down roots or invest in vacation properties in a neatly kept waterfront village. Real estate includes historic homes dating to the 1800s with carefully restored original features, such as hardwood floors, built-in bookcases, and crown molding. Sprawling manors on several acres often come with picturesque names dating back to their original owners. Other housing options include townhomes built in the early 1900s and modern homes and townhomes constructed in recent years.

The Talbot County Board of Education operates public schools serving pre-Kindergarten through 12th grade in St. Michaels. The schools lie on a 55-acre parcel of land south of the Town's business district. The St. Michaels school campus contains the public elementary, middle, and high schools.

Quick Facts

  • Population: 1,049
  • Median Household Income: $61,563
  • Median Home Value: $371,900
  • Median Age: 56.2

Compensation and Benefits

The expected hiring range is $100,000 – $120,000, depending on qualifications, with an excellent benefits package. The Town of St. Michaels is part of the State of Maryland Retirement System.

How to Apply

Applications will be accepted electronically by Raftelis. Applicants complete a brief online form and are prompted to provide a cover letter and resume. Applications will be accepted through January 18, 2022. 


Please direct questions to Catherine Tuck Parrish at and Carly Trimboli at

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