Insurance Executive Assistant Jobs in Frederick, MD

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.

Specifically, you would be responsible for:

• Calendar Management

  • 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

• Email Management

  • 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.

• Operational and Administrative Support

  • 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.

This is a hybrid position based out of our Lansdowne, VA headquarters, requiring in-office presence 2 days per week to support in-person coordination with the executive team.

• 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.

$90,000 - $115,000 annual salary

What Fortreum Offers

We offer a competitive compensation package, where you will be rewarded based on your performance/outcomes and recognized for the value you bring to our business. Our benefits package includes medical insurance, dental insurance, vision insurance, 401K plan with a 4% match, company paid short-term disability, company paid long-term disability, company paid AD&D and life insurance, flex time off, annual bonuses, training stipends, certification reimbursements, access to over 30,000 free online training courses, personal cell phone allowance, new hire and annual home office stipend, spot awards and eleven paid holidays.

An Affirmative Action and Equal Opportunity Employer

Fortreum is an Affirmative Action and Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, or protected veteran status and will not be discriminated against on the basis of disability. If you'd like to view a copy of the company's affirmative action plan or policy statement, please email hr@fortreum.com. If you have a disability and you believe you need a reasonable accommodation in order to search for a job opening or to submit an online application, please e-mail hr@fortreum.com or call 703-594-1460. This email and phone number is created exclusively to assist disabled job seekers whose disability prevents them from being able to apply online. Only messages left for this purpose will be returned. Messages left for other purposes, such as following up on an application or technical issues not related to a disability, will not receive a response.

In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification form upon hire.