Title: Executive Assistant to the Chief Executive Officer
Location: Hybrid/Remote in Elgin, IL (Candidates within Central Time Zone preferred)
Duration: Full-Time
Compensation: $60K – $75K
Work Requirements: US Citizen, GC Holders or Authorized to Work in the US

Position Overview

We are seeking a highly organized, proactive, and resourceful Executive Assistant to provide strategic and administrative support to the Chief Executive Officer. This role extends well beyond traditional executive support responsibilities and serves as a trusted business partner dedicated to enhancing the CEO’s productivity, organization, and effectiveness.

The ideal candidate is adaptable, highly professional, and capable of anticipating needs before they arise. This individual will play a critical role in managing priorities, coordinating key initiatives, streamlining operations, and supporting both professional and select personal responsibilities. Success in this position requires exceptional judgment, discretion, communication skills, and the ability to thrive in a dynamic, fast-paced environment.

While this position is primarily remote, candidates located within the Central Time Zone are strongly preferred. Local candidates available for occasional in-person meetings are a plus but not required.

Key Responsibilities

Executive Support

• Manage and optimize the CEO’s calendar, including meetings, appointments, travel, and strategic planning time.
• Prioritize requests and competing demands to maximize the CEO’s efficiency and effectiveness.
• Coordinate internal and external meetings, ensuring agendas, materials, and logistics are prepared in advance.
• Prepare presentations, reports, briefing materials, and meeting follow-up documentation.
• Maintain task management systems, action items, and accountability processes to ensure key initiatives progress effectively.

Strategic Support

• Manage and maintain executive priorities, strategic initiatives, and tracking systems.
• Conduct research and prepare background briefs in advance of meetings and important business discussions.
• Develop and distribute executive summaries, daily briefings, and status updates.
• Organize ideas, projects, and business opportunities into actionable plans and next steps.
• Anticipate challenges, identify bottlenecks, and proactively implement solutions.

Communication & Relationship Management

• Serve as a liaison between the CEO, internal teams, clients, vendors, and external partners.
• Draft, edit, and manage professional communications on behalf of the CEO.
• Ensure timely follow-up and effective communication across stakeholders.
• Maintain a relationship management system to track key contacts, conversations, and follow-up opportunities.
• Handle highly sensitive and confidential information with discretion and professionalism.

Travel & Logistics Management

• Coordinate complex domestic and international travel arrangements, including flights, accommodations, transportation, itineraries, and reservations.
• Manage travel disruptions and last-minute schedule changes efficiently.
• Process expense reports, reimbursements, and related documentation.
• Coordinate personal and business logistics as needed.

Personal Concierge & Lifestyle Support

• Assist with select personal responsibilities to maximize the CEO’s focus and productivity.
• Coordinate appointments, reservations, gifting programs, special events, and personal projects.
• Manage relationship-building initiatives and strategic gifting efforts.
• Handle miscellaneous requests with professionalism, urgency, and attention to detail.

Operational & Administrative Support

• Support day-to-day business operations and administrative functions.
• Assist with special projects and company-wide initiatives.
• Document and improve internal processes, workflows, and operating procedures.
• Support onboarding efforts and cross-functional coordination when needed.
• Assist with Microsoft 365 administration, shared accounts, calendars, and collaboration tools.

Required Qualifications

• Experience supporting senior executives, founders, CEOs, or business owners.
• Exceptional organizational, planning, and time-management skills.
• Strong written and verbal communication abilities.
• High degree of professionalism, sound judgment, and discretion.
• Proven ability to manage multiple priorities in a fast-paced environment.
• Strong critical-thinking and problem-solving skills.
• Advanced proficiency with Microsoft Office and Microsoft 365, including Outlook, Excel, PowerPoint, Teams, and shared account management.
• Ability to work independently with minimal supervision while maintaining a high level of accountability.

Preferred Qualifications

• Experience directly supporting a CEO, founder, entrepreneur, or business owner.
• Experience within a high-growth, entrepreneurial, or privately held organization.
• Familiarity with CRM platforms, project management tools, and productivity software.
• Demonstrated ability to build systems, processes, and organizational structures from the ground up.
• Experience supporting both executive business functions and personal responsibilities.
• Located within the Central Time Zone and available for occasional in-person meetings.

Ideal Candidate Profile

The successful candidate is more than an administrator; they are a proactive and strategic partner. This individual demonstrates initiative, confidence, professionalism, and strong business judgment. They are comfortable providing recommendations, challenging assumptions when appropriate, and bringing solutions rather than problems.

The ideal Executive Assistant will thrive in an evolving environment, helping establish workflows, optimize processes, and build a highly effective partnership with the CEO. They possess excellent interpersonal skills, a service-oriented mindset, and a commitment to excellence in every aspect of their work.

Compensation & Benefits

• Competitive compensation commensurate with experience and qualifications.
• Flexible work arrangement with primarily remote responsibilities.
• Opportunity to grow into a highly trusted strategic partner role with significant visibility and impact.
• Collaborative onboarding and transition support provided by senior leadership.

Additional Information

The Senior Comptroller will assist with onboarding and provide ongoing support during the transition period to ensure a successful integration into the organization and provide the resources necessary for long-term success.

About INSPYR Solutions
Technology is our focus and quality is our commitment. As a national expert in delivering flexible technology and talent solutions, we strategically align industry and technical expertise with our clients' business objectives and cultural needs. Our solutions are tailored to each client and include a wide variety of professional services, project, and talent solutions. By always striving for excellence and focusing on the human aspect of our business, we work seamlessly with our talent and clients to match the right solutions to the right opportunities. Learn more about us at inspyrsolutions.com.

INSPYR Solutions provides Equal Employment Opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, sex, national origin, age, disability, or genetics. In addition to federal law requirements, INSPYR Solutions complies with applicable state and local laws governing nondiscrimination in employment in every location in which the company has facilities.

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