Senior Executive Assistant to Senior Leader - 21726

• Work arrangement: Fully remote
• Working hours: U.S. business hours spanning Mountain to Eastern Time. The executive is based in Mountain Time; much of the business runs on Eastern. Flexibility across Mountain, Central, and Eastern — leaning Eastern — is required.
• Structure: Dedicated full-time to one executive. This is not a shared or multi-client role.

We are an established, U.S.-headquartered global leader in risk, benefits, and claims solutions, serving major employers, insurers, and public-sector organizations across dozens of countries. We operate at enterprise scale in a highly regulated, data-sensitive industry, pairing deep domain expertise with advanced, AI-enabled technology.

Our environment is fast-paced and high-stakes, with constant collaboration across senior leadership, clients, and internal stakeholders. Discretion, professionalism, and sound judgment are core to how we operate.

(Company name withheld at this stage of the search and shared with shortlisted candidates.)

This role exists because a senior executive needs a true partner — not an administrative task-taker. She operates in a demanding, high-visibility environment with a calendar that is consistently full and priorities that shift constantly.

The person in this seat functions as an extension of the executive: someone who sees what needs to happen and acts on it confidently, rather than waiting for direction. This is a senior Executive Assistant role with chief-of-staff instincts — anticipating needs, protecting the executive's time and attention, and representing her credibly to internal and external stakeholders.

If you are a generalist virtual assistant looking for a task list, this is not the role. If you are a seasoned executive partner who thrives on ownership, judgment, and trust, read on.

• Own and actively manage a complex, high-volume calendar, resolving competing priorities without being asked
• Coordinate meetings across multiple time zones, internal teams, clients, and external partners
• Protect the executive's time by filtering, prioritizing, and making judgment calls on what requires her attention

• Serve as a professional point of contact on the executive's behalf with senior leaders, clients, and internal teams
• Draft, review, and send polished written communications that reflect the executive's voice and standards
• Manage follow-ups and ensure commitments and action items move forward to completion

• Anticipate needs and surface issues before they become problems
• Act confidently and independently within the scope of the executive's priorities
• Keep multiple workstreams organized and moving in parallel

• Prepare agendas, briefing materials, and pre-reads ahead of key meetings
• Coordinate domestic and international travel, logistics, and itineraries
• Manage expense reporting and reconciliation

• Handle highly confidential and sensitive information with airtight discretion
• Operate within the company's security, confidentiality, and data-handling protocols at all times

• Work fluently in Outlook, Microsoft 365, and Teams
• Use AI tools (e.g., Microsoft Copilot, ChatGPT) to increase speed, quality, and output
• Maintain organized digital systems for documents, communications, and tracking

• 7+ years of Executive Assistant experience supporting C-suite or very senior executives
• Experience operating in large, complex, or regulated organizations
• Demonstrated track record handling confidential and sensitive information with discretion
• Excellent written and verbal English communication
• Proficiency with Outlook, Microsoft 365, and Teams
• Ability to consistently work U.S. business hours across the Mountain–Eastern range
• Fast, accurate typing (this role carries an elevated typing-speed and accuracy standard)
• Reliable remote work environment and strong internet connectivity

• Chief of Staff exposure or experience operating beyond a traditional EA scope
• Experience directly supporting executives at U.S.-based enterprises or multinationals
• Fluency with AI productivity tools (Microsoft Copilot, ChatGPT, or similar)
• Experience in a regulated industry (insurance, financial services, healthcare, or legal)
• Based in Latin America or South Africa

• Highly organized and genuinely proactive — you act before being asked
• Calm under pressure, with excellent judgment on what matters and what can wait
• Discreet and trustworthy with sensitive information
• A polished communicator with real executive presence
• Technically sharp and comfortable adopting new tools, including AI
• Confident operating as an extension of a senior leader, not just an assistant to one