Senior Staff Assistant (CSR III - Streets & Drainage Division)

Are you a highly organized individual who enjoys working with the public and who thrives in a fast-paced environment? Our Streets & Drainage Division is looking for a Sr. Staff Assistant to provide exceptional support to the public and to internal departments to keep things running smoothly.

• Job Title: Senior Staff Assistant (CSR III - Streets & Drainage Division)
• Category: Full-Time
• Application Closing Date: Closing Date July 16, 2026

Salary and Benefits:

• $18.35 Per Hour Minimum
• Annual Step for Performance Pay Adjustments
• 12 Paid Holidays Per Year
• 12 Vacation Days Minimum, Earned Per Year
• 12 Sick Days Earned Per Year
• Medical, Dental, Vision, and Life Insurance Benefits
• 401(a) Retirement Plan and Social Security Coverage
• 457 Deferred Plan Options
• Education/Tuition Assistance Program; and Training and Development Opportunities
• Employee Assistance Program – to include Mental Health Assistance/Services

Essential Job Functions

Performs administrative, procedural, and related support work to assist the Streets & Drainage Division Superintendent and division staff in the performance of their duties.

Provides customer service and serves as a primary point of contact for the division by responding to inquiries from residents, community members, contractors, vendors, and other City departments. Receives, enters, tracks, and monitors citizen requests, concerns, and work orders related to streets, drainage, rights-of-way, and related infrastructure. Retrieves and reviews information from departmental records, work order systems, maps, and other resources to provide accurate information and assistance or routes requests to the appropriate personnel for resolution. Communicates with residents regarding the status of requests and maintains accurate records within the City's asset management and work order systems.

Assists in the preparation, proofreading, processing, and distribution of correspondence, reports, forms, permits, and other division documents. Maintains division records and files, processes incoming and outgoing mail, and ensures the timely distribution of information.

Coordinates meetings, training activities, and other division functions by preparing agendas, assembling materials, recording meeting minutes when required, maintaining calendars, and scheduling appointments, meetings, and training sessions.

Provides support with personnel, fiscal, and procurement items by processing timesheets, leave requests, personnel action forms, invoices, purchase orders, procurement card documentation, requisitions, and related records while maintaining confidentiality of sensitive information. Assists with tracking division expenditures and ordering office supplies, materials, and equipment as needed.

Utilizes City-approved software and technology platforms for records management, financial processing, timekeeping, work order management, asset management, project tracking, and other administrative functions. Operates standard office equipment including computers, scanners, copiers, calculators, and related equipment.

Assists with public outreach efforts, special projects, and division events as assigned. Maintains professional and technical knowledge through training, workshops, professional publications, and participation in relevant organizations and activities.

Must be available to perform essential job functions outside regular work hours when required, including emergency response activities and special projects where administrative support is deemed necessary.

Performs other related duties as assigned. This is not intended to be an all-inclusive listing of essential job functions; the performance of other essential functions may be required.

Knowledge, Skills & Abilities

• Knowledge of modern office practices and procedures, customer service principles, and business English, including grammar, spelling, and punctuation. Knowledge of records management best practices, as well as standard office equipment and technology, including computers, multi-line telephone systems, copiers, and scanners. Knowledge of Microsoft Office applications and other commonly used municipal software systems, including work order and asset management platforms.
• Ability to learn and apply City policies, procedures, organizational structure, and departmental operations, as well as timekeeping processing system, accounts payable, and purchasing policy and procedures; learn and utilize multiple softwares effectively; retrieve, interpret, and communicate information from electronic systems, records, maps, and other resources to assist residents and support departmental operations; maintain accurate electronic and paper records, organize and prioritize multiple tasks, and meet deadlines in a fast-paced environment; and prepare, proofread, and process correspondence, reports, forms, and other documents with accuracy and attention to detail.
• Ability to communicate clearly and professionally, both orally and in writing, to establish and maintain effective working relationships with residents, contractors, vendors, and City employees; exercise sound judgment, discretion, and confidentiality when handling sensitive information; work independently with minimal supervision while demonstrating initiative and adaptability; understand and follow oral and written instructions; operate standard office equipment and software systems, and type accurately and efficiently.

Minimum Education & Experience

• Graduation from an accredited high school or possession of an acceptable equivalency diploma.
• Two years’ experience of clerical or administrative support work.
• An equivalent combination of education, training, and experience that is determined to be directly related to the foregoing specific requirements may be substituted.

Special Requirements:

• Possession of a valid Florida driver’s license with a good driving record as determined by the City of Winter Haven.
• Absence of non-prescribed controlled substances in the applicant’s system as verified by a laboratory approved by the City of Winter Haven.

Physical / Environmental Factors:

• Must have the physical ability, strength, and flexibility to perform the job functions in the work environment.
• Reasonable accommodations will be made for otherwise qualified individuals with a disability.

AN EQUAL EMPLOYMENT OPPORTUNITY EMPLOYER AND A DRUG-FREE WORKPLACE

Our Mission: Enriching lifestyle through exceptional service.