Executive Assistant – Office 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
.

• 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

• 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

• 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

• 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

• 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

• 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

• 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

• 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…