Executive Assistant

Overview

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

Company: Dynamic Service Solutions (DSS) & Affiliated Companies

Location: Hybrid / On-site (as applicable)

Reports to: CEO, COO & CFO Type: Full-Time

Position Overview:

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.

• 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

• 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