Senior Executive Assistant

Fortreum•Leesburg, VA

10d•$90,000 - $115,000•Hybrid

About The Position

Fortreum is a trusted leader in cloud and cybersecurity services, ranked among the Top 5 FedRAMP Third Party Assessment Organizations (3PAO). With the addition of Kovr.AI, we have expanded our capabilities to include advanced cyber risk quantification and analytics, enabling organizations to better understand, measure, and communicate risk. Together, we deliver independent, third-party, vendor-agnostic regulatory assessment and advisory services, alongside advanced cybersecurity offensive and compliance technical solutions. Our comprehensive service portfolio spans regulatory compliance frameworks including FedRAMP, CMMC, FISMA, SOC, PCI, ISO, and HIPAA. Working with Fortune 500 companies and leading cloud service providers, we’ve built our reputation on service-delivery excellence and an unwavering commitment to client success. Our continued rapid growth creates exceptional opportunities for driven professionals to make their mark in the cybersecurity industry—guided by our core values: quality above all, a customer-driven mindset, autonomy, and personal accountability. On our team, you'll have the opportunity to work directly alongside the executives shaping Fortreum's strategy and growth. This position offers a motivated, detail-oriented professional the chance to sit at the center of the organization — gaining exposure to high-level decision-making, building relationships across leadership, and playing a pivotal role in keeping Fortreum's C-suite focused on what matters most.

Requirements

5+ years supporting senior executives with heavy emphasis on calendar and inbox management, ideally across multiple executives simultaneously.
Advanced proficiency in Outlook/Microsoft 365 (calendar tools, rules, delegate access, focus time features).
Excellent judgment in prioritization: able to distinguish urgent vs. important without hand-holding.
Strong written communication skills for drafting emails in an executive's voice
High discretion with confidential and sensitive information.
Comfortable managing ambiguity and shifting priorities across four distinct working styles.
Experience in government contracting, consulting, or professional services.
Hands-on experience with SharePoint, Teams and other Microsoft 365 collaboration tools.

Responsibilities

Own and manage complex, high-volume calendars for five executives (CEO, President, CSO/CRO, CTO, CFO), resolving conflicts and making real-time judgment calls on priority.
Proactively schedule and reschedule meetings based on shifting business priorities, without requiring constant executive input.
Block focus time and protect executives' calendars from over-scheduling; flag when a week is unsustainable.
Anticipate scheduling needs around recurring cycles (MFRs, board meetings, QBRs, client engagements) and build calendars proactively rather than reactively.
Monitor and triage inboxes for executives, flagging urgent items and filtering low-priority or spam content
Draft responses on executives' behalf for routine correspondence, using appropriate tone and judgment on when executive input is needed.
Maintain a clear system (folders, flags, or task tracking) so nothing time-sensitive is missed.
Follow up on outstanding threads and ensure timely responses to internal and external stakeholders.
Exercise discretion in distinguishing what needs executive eyes immediately vs. what can wait or be delegated.
Process expense reports and manage budgets related to executive operations.
Maintain organized filing systems for Board and executive-level documentation.
Support special projects as assigned by executives.
Prepare brief daily/weekly summaries of calendar and inbox priorities for each executive.
Coordinate travel logistics (domestic and international) tied to calendar commitments.
Support meeting prep by ensuring relevant materials are attached or linked to calendar invites.
Act as a gatekeeper: managing incoming meeting requests and inbox volume so executives can focus on strategic work.