Executive Assistant to the CEO

R3 LLC • Frederick, MD

38d • $80,000 - $115,000 • Remote

About The Position

As the Executive Assistant to the CEO at R3, you’ll be the gatekeeper, strategist, and ultimate linchpin supporting one of the most dynamic leaders in the IT services industry. This role is the central command post—protecting time, filtering noise, and keeping the CEO focused on driving R3’s strategic growth and client success while the rest of the organization powers forward at full speed. If your natural habitat is a high-velocity tech environment where precision and adaptability matter, this is your seat. You’ll join a team of hard-working, dedicated, and fun professionals in a culture where urgency is standard, confidentiality is absolute, and flawless execution keeps our clients connected and our business moving.

Requirements

• Bachelor’s degree or 5+ years supporting executive leadership
• Proven success in a fast-paced, high-visibility support role
• Advanced proficiency in Microsoft Outlook, Word, Excel, and PowerPoint; comfortable learning and leveraging new technology and tools
• Experience managing executive calendars, travel, and communication workflows
• Demonstrated ability to preserve confidentiality and use sound judgment
• Agile, adaptable, and quick to recalibrate when priorities shift
• High-energy self-starter who thrives in organized chaos and keeps things moving with purpose and precision
• Extreme attention to detail, ensuring nothing slips, nothing repeats, nothing is missed
• Clear and polished communicator—both written and verbal
• Anticipatory mindset, proactively identifying needs and solving problems before they surface
• Exceptionally organized with elite time-management skills
• Strong relationship builder who can navigate diverse personalities with patience, tact, and a sense of humor
• Confident with a strong backbone—able to push back respectfully and advocate for priorities when needed

Responsibilities

• Serve as the primary point of contact and trusted gatekeeper for the CEO- controlling communications, priorities, and information flow across all levels of the organization
• Manage complex calendars, meetings, travel, and event logistics with precision and proactive problem-solving
• Draft, edit, and send professional communications on behalf of the CEO, ensuring consistency, accuracy, and tone alignment
• Anticipate needs by researching, preparing briefing materials, and providing decision-ready information that keeps the CEO focused on high-impact goals
• Drive accountability by maintaining leadership action trackers, following up on deliverables, and ensuring progress is communicated clearly and on time
• Manage sensitive matters with absolute confidentiality, sound judgement, and professionalism, representing the CEO and R3 in a positive, composed manner
• Coordinate with executives, internal teams, clients, and external partners to support the CEO’s initiatives and business relationships
• Maintain organized systems for records, expenses, timekeeping, and reports—ensuring timely and accurate updates for leadership
• Own and execute high-impact projects—from urgent business priorities to personal initiatives—with agility and flawless follow-through
• Bring energy, precision, and discretion to every task, helping the CEO stay one step ahead in a fast-moving IT services environment

Benefits

• Competitive wages to reflect your experience and skills.
• Comprehensive medical, dental, and vision insurance plans to keep you and your family healthy.
• 401(k) with company match to help you plan for the future.
• Flexible time off policies to ensure you maintain a healthy work-life balance.
• We offer many remote opportunities, allowing you to work wherever you want.
• We are committed to creating a positive impact on society and contributing to a better world--we're involved in our community and encourage our employees to do the same.
• We are reshaping the industry and the way it thinks about technology and service.
• We strive to be better and encourage our employees to do the same by offering training incentives and bonuses to help you and your career grow.
• The opportunity to be a part of an amazing team.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 101-250 employees