Title: Executive Assistant to the Chief Executive Officer
Location: Hybrid/Remote in Elgin, IL (Candidates within Central Time Zone preferred)
Duration: Full-Time
Compensation: $65K – $75K
Work Requirements: US Citizen, GC Holders or Authorized to Work in the US

Executive Assistant to the Chief Executive Officer

Position Overview

We are seeking an exceptional Executive Assistant to serve as a strategic partner to the Chief Executive Officer. This role extends far beyond traditional administrative support and combines executive assistance, strategic project coordination, relationship management, personal concierge services, and operational leadership.

The ideal candidate is highly organized, proactive, resourceful, and capable of anticipating needs before they arise. This individual will act as a force multiplier for the CEO by managing priorities, protecting time, streamlining communications, coordinating initiatives, and ensuring consistent progress toward strategic goals. The Executive Assistant will serve as a trusted advisor, gatekeeper, organizer, and execution partner who helps maximize the CEO's effectiveness both professionally and personally.

Key Responsibilities

Executive & Strategic Support

• Manage and optimize the CEO's calendar, priorities, strategic initiatives, and daily workflow.
• Maintain accountability systems for key business objectives, projects, and quarterly priorities.
• Organize ideas, opportunities, and initiatives into actionable plans with clear ownership and deadlines.
• Prepare executive summaries, strategic updates, reports, presentations, and briefing materials.
• Anticipate challenges, identify bottlenecks, and proactively implement solutions.
• Convert meeting notes, discussions, and ideas into structured action plans and follow-up items.
• Maintain tracking systems for goals, milestones, deliverables, and organizational priorities.
• Support special projects and company-wide initiatives as assigned.

Email & Communication Management

• Serve as the CEO's communication gatekeeper by managing inbox organization and prioritization.
• Draft, edit, and manage professional correspondence on behalf of the CEO.
• Prepare first-draft responses in the CEO's voice for recurring communications.
• Monitor unanswered emails, stalled conversations, and follow-up opportunities.
• Summarize lengthy email threads into concise action-oriented recommendations.
• Maintain communication templates and ensure consistent messaging across stakeholders.
• Coordinate communications with clients, vendors, investors, partners, team members, and external contacts.
• Handle highly confidential information with discretion and professionalism.

Calendar & Time Management

• Design, manage, and protect the CEO's ideal weekly schedule.
• Coordinate meetings, appointments, travel, strategic planning sessions, and focus blocks.
• Ensure meetings align with organizational priorities and strategic objectives.
• Prepare agendas, materials, objectives, and follow-up documentation for meetings.
• Resolve scheduling conflicts and manage competing priorities.
• Build travel, preparation, and recovery time into schedules as appropriate.
• Audit calendar effectiveness and recommend adjustments to improve productivity and energy management.
• Ensure every meeting has a clear purpose, desired outcome, and next step.

Project & Task Management

• Create and maintain prioritized task lists aligned with company objectives.
• Manage project timelines, milestones, deliverables, and accountability processes.
• Track weekly, monthly, and quarterly goals.
• Coordinate with internal teams to ensure progress on strategic initiatives.
• Monitor open action items and facilitate completion or delegation.
• Provide regular progress updates and executive dashboards.
• Establish systems and workflows that improve organizational efficiency and execution.

Meeting Preparation & Research

• Prepare executive briefing documents for meetings, events, and business discussions.
• Conduct research on companies, industries, prospects, partners, and stakeholders.
• Develop meeting talking points, discovery questions, and discussion frameworks.
• Compile relevant background information, previous interactions, and strategic context.
• Create post-meeting summaries and track follow-up actions.
• Maintain a library of recurring briefing materials and standard operating procedures.

Relationship Management & Personal CRM

• Maintain a comprehensive relationship management system for key contacts.
• Track interactions, follow-ups, milestones, and relationship-building opportunities.
• Coordinate outreach, thank-you notes, gifts, and strategic touchpoints.
• Manage executive networking activities and relationship development initiatives.
• Maintain accurate records of client, partner, vendor, investor, and personal contacts.
• Support LinkedIn relationship management and professional networking activities.
• Prepare periodic relationship reviews and engagement recommendations.

Travel, Logistics & Event Coordination

• Coordinate complex domestic and international travel arrangements.
• Manage itineraries, accommodations, transportation, reservations, and travel documentation.
• Handle travel disruptions and last-minute schedule changes.
• Process expenses, reimbursements, and travel-related documentation.
• Coordinate conferences, networking events, client meetings, and executive appearances.
• Manage personal and business logistics with professionalism and urgency.

Personal Concierge & Strategic Gifting

• Support select personal responsibilities to maximize the CEO's focus and effectiveness.
• Coordinate appointments, reservations, special events, and personal projects.
• Manage strategic gifting programs, including sourcing, budgeting, personalization, and delivery.
• Maintain records of important dates, milestones, preferences, and gifting history.
• Coordinate client appreciation initiatives and relationship-building activities.
• Draft personalized notes and correspondence for gifts and special occasions.

Operational & Administrative Support

• Support daily business operations and administrative functions.
• Document and improve internal processes, systems, and workflows.
• Assist with onboarding, cross-functional coordination, and operational initiatives.
• Manage Microsoft 365 tools, shared calendars, collaboration platforms, and administrative systems.
• Develop and maintain standard operating procedures to improve scalability and efficiency.
• Identify opportunities for automation and process optimization.

Required Qualifications

• Experience supporting senior executives, founders, CEOs, or business owners.
• Exceptional organizational, project management, and time-management skills.
• Outstanding written and verbal communication abilities.
• Proven ability to manage multiple priorities in a fast-paced environment.
• Strong critical thinking, problem-solving, and decision-making skills.
• High degree of professionalism, discretion, confidentiality, and sound judgment.
• Advanced proficiency with Microsoft 365, including Outlook, Excel, PowerPoint, Teams, and shared account management.
• Experience with CRM platforms, project management tools, productivity software, and calendar management systems.
• Ability to work independently with minimal supervision while maintaining a high level of accountability.
• Demonstrated success building systems, processes, and organizational structures from the ground up.

Preferred Qualifications

• Experience directly supporting a CEO, founder, entrepreneur, or business owner.
• Experience in a high-growth, entrepreneurial, or privately held company environment.
• Background supporting both business operations and personal executive responsibilities.
• Experience with relationship management, executive communications, and strategic project coordination.
• Familiarity with workflow automation and productivity optimization tools.
• Central Time Zone location preferred with availability for occasional in-person meetings.

Ideal Candidate Profile

The ideal Executive Assistant is far more than an administrator. They are a trusted strategic partner who anticipates needs, solves problems before they arise, and enables the CEO to focus on high-impact activities. This individual combines exceptional attention to detail with strong business acumen, operates with confidence and discretion, and consistently brings solutions rather than problems.

They thrive in dynamic environments, build scalable systems, communicate effectively across all levels of an organization, and take ownership of outcomes. Their ultimate goal is to create leverage for the CEO by protecting time, improving execution, strengthening relationships, and ensuring organizational priorities move forward efficiently.

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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