Executive Assistant, Multi-Executive Support

About Coalfire

Coalfire is on a mission to make the world a safer place by solving our clients’ hardest cybersecurity challenges. We work at the cutting edge of technology to advise, assess, automate, and ultimately help companies navigate the ever-changing cybersecurity landscape. We are headquartered in Chicago, Illinois with offices across the U.S. and U.K., and we support clients around the world.

But that’s not who we are – that’s just what we do.

We are thought leaders, consultants, and cybersecurity experts, but above all else, we are a team of passionate problem-solvers who are hungry to learn, grow, and make a difference.

Position Summary

The Executive Assistant provides high-level administrative and operational support to nine senior executives across the organization. This role requires exceptional judgment, organizational excellence, and the ability to manage complex, shifting priorities in a fast‑paced environment. The EA acts as a strategic partner - anticipating needs, streamlining workflows, and ensuring executives are fully supported and equipped to focus on organizational priorities.

This individual will report to the Chief People Officer and will be a central coordination point for the leadership team, maintaining confidentiality, professionalism, and reliability at all times.

What You'll Do:
• Executive Support
• Manage complex calendars across multiple time zones for nine executives, ensuring proactive prioritization and alignment with strategic goals.
• Coordinate and schedule internal/external meetings, board-related sessions, customer meetings, candidate interviews, and cross-functional engagements.
• Prepare executives in advance of meetings, including compiling briefings, agendas, presentations, and relevant background materials.
• Handle correspondence on behalf of executives, including drafting communications, triaging requests, and tracking follow‑ups.
• Operational & Administrative Excellence
• Develop and maintain streamlined workflows across the leadership team to improve efficiency and reduce administrative bottlenecks.
• Plan and execute logistics for all executive travel; including leadership offsites, team meetings, and company-wide events.
• Assist with budget tracking, invoice processing, expense reporting, and purchase orders.
• Maintain organized digital filing systems and shared knowledge repositories.
• Cross-Functional Coordination
• Serve as a liaison between executives and key internal/external stakeholders, ensuring clarity, responsiveness, and follow‑through.
• Partner with People, Finance, Legal, Communications, and other teams to support initiatives, timelines, and deliverables.
• Support cross-functional projects by gathering inputs, tracking milestones, and helping executives stay on schedule.
• Confidentiality & Communications
• Handle sensitive information with the highest level of discretion.
• Represent executives with professionalism, polish, and proactive communication - both internally and externally.
• Draft, edit, and proofread executive communications, presentations, and documents.
• Special Projects
• Support organizational initiatives as assigned by the CPO, including culture programs, talent-related efforts, and strategic planning cycles.
• Conduct research, compile data, and produce reports or presentations as needed.

What You'll Bring:
• 5+ years of experience supporting senior executives; experience supporting multiple leaders simultaneously strongly preferred.
• Exceptional organizational and time-management skills with the ability to balance multiple priorities and stakeholders.
• Strong written and verbal communication skills; ability to craft clear, concise, and professional communications.
• High level of discretion, emotional intelligence, and sound judgment.
• Proficiency with Microsoft 365 (Outlook, Teams, Word, Excel, PowerPoint), Zoom, and other collaboration tools.
• Proven ability to thrive in a fast-paced, high-expectation environment.
• Experience supporting C‑level leaders or extended executive teams.
• Experience in a dynamic, high-growth, or matrixed organization.
• Project management experience or formal training.
• Background supporting People/HR leadership is a plus.

Why You’ll Want to Join Us

At Coalfire, you’ll find the support you need to thrive personally and professionally. In many cases, we provide a flexible work model that empowers you to choose when and where you’ll work most effectively – whether you’re at home or an office.

Regardless of location, you’ll experience a company that prioritizes connection and wellbeing and be part of a team where people care about each other and our communities. You’ll have opportunities to join employee resource groups, participate in in-person and virtual events, and more. And you’ll enjoy competitive perks and benefits to support you and your family, like paid parental leave, flexible time off, certification and training reimbursement, digital mental health and wellbeing support membership, and comprehensive insurance options.

At Coalfire, equal opportunity and pay equity is integral to the way we do business. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or status as a protected veteran. Coalfire is committed to providing access, equal opportunity, and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. To request reasonable accommodation to participate in the job application or interview process, contact our Human Resources team at [email protected].