Executive Assistant – Office of the Executives (CEO, COO & CFO)

Dynamic Service Solutions (DSS) is seeking an Executive Assistant to support the Office of the Executives, serving the CEO, COO, and CFO across all DSS-affiliated companies. This is a mission-critical role designed for an experienced professional who operates with executive judgment, discretion, and strategic awareness.

This position extends beyond traditional administrative support. The Executive Assistant functions as a trusted partner and operational anchor, ensuring executive effectiveness, organizational alignment, and seamless coordination across leadership, teams, and entities. The ideal candidate brings both professional warmth and firm business acumen, embodying DSS’s commitment to restoring human dignity, enhancing safety, and performing with a level of excellence.

Core Responsibilities

Executive Partnership & Strategic Support

• Provide high-level support to the CEO, COO, and CFO across multiple companies and initiatives

• Serve as a central coordination point within the Office of the Executives

• Anticipate executive needs and proactively manage priorities, deadlines, and follow-ups

• Act as a gatekeeper and filter to protect executive focus and time

• Maintain operational continuity during executive travel or absences

Executive Communications

• Draft, edit, and send emails, memos, directives, and formal correspondence on behalf of executives

• Ensure all communications reflect DSS leadership tone: clear, respectful, firm, and mission-aligned

• Prepare executive briefings, talking points, summaries, and internal announcements

• Capture meeting outcomes and produce concise recaps with clear next steps and accountability

Calendar, Meetings & Logistics Management

• Manage complex, high-volume calendars for three executives with strategic foresight

• Coordinate internal and external meetings, including executive leadership and board-related engagements

• Prepare agendas, materials, and pre-reads to ensure executive readiness

• Track deliverables, deadlines, and commitments across multiple business entities

• Coordinate travel and logistics as needed

Cross-Functional & Operational Coordination

• Liaise with executive leadership, department heads, administrative staff, and external partners

• Support preparation of board materials, leadership reports, and operational documentation

• Maintain systems to track executive decisions, projects, and organizational priorities

• Identify risks, inefficiencies, or gaps and surface thoughtful recommendations

• Ensure consistency and alignment across all companies supported by the executive team

Confidentiality, Integrity & Professional Presence

• Handle sensitive, confidential, and time-critical information with discretion and integrity

• Represent the Office of the Executives with professionalism, kindness, and authority

• Uphold DSS values and leadership standards in all internal and external interactions

Qualifications

Required

• Bachelors Degree in Business Administration or relevant field preferred

• 7–10 years of experience supporting C-suite executives in complex organizations

• Proven experience drafting executive-level communications independently

• Exceptional written, verbal, and interpersonal communication skills

• Strong organizational systems and attention to detail

• High emotional intelligence, sound judgment, and professional maturity

• Proficiency in Microsoft 365 or Google Workspace, Teams, Zoom, and calendar management tools

Preferred

• Experience supporting multiple executives simultaneously

• Background in operations, compliance-driven environments, government contracting, healthcare, nonprofit, or regulated industries

• Exposure to board support and executive leadership teams

• Experience functioning in an Executive Assistant / Chief of Staff-style role

Key Attributes for Success

• Calm, kind, and confident presence

• Business-driven, solutions-oriented mindset

• Ability to manage ambiguity, shifting priorities, and competing demands

• Proactive, dependable, and highly trusted

• Deep respect for mission-driven work and organizational impact

Work is performed mostly in an office setting. Some overnight travel; public speaking, evening and weekend work are requirements of the position. Regular computer works also required. While performing the duties of this job, the employee is required to stand; walk; sit; finger, handle, or feel objects, or controls; reach; climb stairs; balance; stoop, kneel, or crouch; talk and hear. The employee must occasionally lift and/or move up to 20 pounds. Specific vision abilities required by the job include close vision, distance vision, color vision, peripheral vision, depth perception, and the ability to adjust focus.

The physical demands and work environment characteristics described above are representative of the physical capabilities that must be met by an employee and the working conditions that an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

This job description is intended to convey information essential to understanding the scope of the position and it is not intended to be an exhaustive list of skills, efforts, duties, responsibilities or working conditions associated with the position.

Dynamic Service Solutions is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, political affiliation, marital status, genetic information, disability, age, military service or veteran status, parental status, or other non-merit factor. Dynamic Service Solutions is also committed to comply with all fair employment practices regarding citizenship and immigration status.

 We participate in E-Verify.