Senior Executive Assistant

Simplify Recruiting; Aurora (IL); On-site; USD 90,000 - 130,000; Full time

Job summary

Simplify Recruiting is seeking a Senior Executive Assistant to provide high‑level support to the Executive Chair and three CEOs across a healthcare technology group. You will manage complex calendars, communications, global travel, and stakeholder coordination, acting as a trusted partner to senior leadership in a fast‑paced, global setting.

This role emphasizes discretion, proactive execution, and cross‑functional collaboration with HR, IT, Finance, and partner teams to enable executives to

Qualifications

• 7+ years supporting C-suite or senior executive leadership.
• Demonstrated experience supporting multiple executives simultaneously.
• Proven ability to operate in fast-paced, high-pressure environments.

Responsibilities

• Own and manage complex, multi-time-zone calendars across four senior leaders.
• Draft, review, and manage professional executive correspondence.
• Coordinate across internal teams, clients, partners, and external stakeholders.
• Track action items from meetings and ensure timely closure.
• Plan and manage domestic and international travel with detailed itineraries.
• Prepare board materials, presentations, and executive briefings.
• Support executive participation in conferences and key engagements.
• Build strong working relationships with other EAs and Chiefs of Staff.

Skills

Calendar management

Executive support

Travel planning

Stakeholder coordination

Discretion

AI-assisted writing

Time-zone coordination

Communication

Microsoft 365

Tools

Microsoft 365

Outlook

Teams

PowerPoint

Excel

Job description

The Senior Executive Assistant will provide high-level support to the Executive Chair and three CEOs, managing complex calendars, executive communications, global travel, stakeholder coordination, and day-to-day executive operations. This role requires exceptional organization, discretion, and the ability to anticipate priorities and drive follow-through in a fast-paced, global environment.

About the Role

Our client is seeking a high-caliber Senior Executive Assistant to support the Executive Chair and three CEOs across a group of healthcare technology businesses.

This is a high-impact, high-visibility role at the center of executive operations. The position requires someone who can manage complexity, anticipate needs, and execute with precision across calendars, communication, travel, and stakeholder engagement.

You will operate as a trusted partner to senior leadership, enabling executives to function effectively at scale in a fast-paced, global environment.

Key Responsibilities

Executive Calendar & Priority Management

• Own and manage complex, multi-time-zone calendars across four senior leaders.
• Proactively resolve conflicts and ensure optimal prioritization of executive time.
• Act as a gatekeeper for meeting requests and communications.
• Ensure timely follow-ups and maintain strong execution discipline.

Executive Communication & Coordination

• Draft, review, and manage professional executive correspondence.
• Coordinate across internal teams, clients, partners, and external stakeholders.
• Track action items from meetings and ensure timely closure.
• Prepare summaries, notes, and structured updates to support executive decision-making.

Global Travel & Logistics

• Plan and manage domestic and international travel, including U.S.–India coordination.
• Prepare detailed itineraries incorporating meeting context, stakeholders, and logistics.
• Manage travel bookings, required documentation, and expense reconciliation.
• Coordinate CXO-level customer and partner visits end-to-end.
• Manage logistics including scheduling, A/V readiness, catering, and meeting flow.
• Build and maintain strong working relationships with Executive Assistants and Chiefs of Staff at customer and partner organizations.

Executive Office Operations

• Prepare board materials, presentations, executive briefings, and other leadership communications.
• Manage confidential documents and sensitive information with a high degree of discretion.
• Support executive participation in conferences, events, and other key engagements.

Global Coordination

• Work seamlessly across time zones, including close coordination with India-based teams.
• Act as a bridge between geographies to support effective scheduling, communication, and execution.
• Coordinate with HR, IT, Finance, and other internal functions on behalf of the executive office.

Operational Efficiency & Continuous Improvement

• Identify opportunities to improve workflows, streamline processes, and enhance responsiveness.
• Leverage modern tools and technologies to improve productivity, including AI-based tools for drafting communications, summarizing information, and managing recurring administrative workflows.
• Bring a systems-oriented approach to task management, reducing manual effort and improving execution speed.

What We’re Looking For

Experience

• 7+ years of experience supporting C-suite or senior executive leadership.
• Demonstrated experience supporting multiple executives simultaneously.
• Proven ability to operate effectively in fast-paced, high-pressure environments.

Skills & Capabilities

• Exceptional attention to detail and follow-through.
• Strong written and verbal communication skills.
• Advanced proficiency in Microsoft 365, including Outlook, Teams, PowerPoint, and Excel.
• Strong executive calendar and domestic/international travel management expertise.
• Ability to use AI tools and modern technology effectively to improve productivity and quality of output.
• Proactive and anticipatory in approach.
• Highly organized with strong systems thinking.
• Calm under pressure with the ability to manage competing priorities.
• Professional, warm, polished, and confident when interacting with senior executives and external stakeholders.
• Highly discreet and trustworthy when handling confidential or sensitive information.

Preferred Background

• Experience within healthcare, healthcare technology, SaaS, or professional services environments.
• Experience supporting executives in global organizations.
• Exposure to India-based teams or U.S.–India business operations is preferred.