Executive Assistant - IntelliScript (Remote)

Milliman • Chicago, IL

8d • Remote

About The Position

The Executive Assistant will serve as a trusted, high‑discretion partner to three of our Executive Leaders, combining best‑in‑class executive support with hands‑on operational coordination. The role protects and optimizes each Executive’s time, orchestrates calendars, travel, expenses, and communications, and drives the preparation and follow‑through for high‑stakes meetings. Acting as a central coordination point, this person will bring structure, cadence, and clarity across priorities, standardize processes and shared systems, and leverage AI tools to elevate speed and quality of deliverables. The ideal hire has supported C‑suite leaders in complex environments, anticipates needs, adapts to different leadership styles, and can coach us on how to get the most from the EA function while flexing to urgent needs as they arise.

Requirements

• 10+ years of experience supporting senior executives (C‑suite) in fast‑paced, complex, multi‑stakeholder environments; experience supporting more than one leader simultaneously
• Demonstrated mastery of calendar/scheduling strategy, travel logistics, expense management, and proactive gatekeeping
• Proven track record orchestrating high‑stakes meetings, including agenda design, pre‑reads, materials, facilitation support, and action follow‑through
• Strong project management skills: defining scope/timelines, managing dependencies, and driving to on‑time, high‑quality outcomes
• Advanced proficiency with Microsoft 365 (Outlook, Teams, SharePoint, PowerPoint, Excel, OneNote); comfort owning shared systems and standard
• Demonstrated use of AI tools to expedite meeting notes, summaries, schedule optimization, and deck creation; ability to coach others on effective AI workflows
• Experience with travel/expense platforms (e.g., Concur) and basic billing/invoicing workflows
• Exceptional written and verbal communication; ability to craft concise, executive‑ready materials and emails
• High integrity and discretion; sound judgment in prioritization and handling confidential information
• High emotional intelligence; able to adapt style to three different executive personalities and stakeholder needs
• Demonstrated ability to anticipate needs, think several steps ahead, and proactively remove friction for executives
• Experience standardizing workflows, templates, and naming conventions; building EA operating playbooks
• Flexibility to support urgent after‑hours needs with a balanced approach to work/life
• The ability to work effectively as part of a team, optimize a team’s performance, build relationships and contribute to a positive team dynamic
• Manage moderate to high risk and take calculated risks to achieve goals
• The ability to facilitate complex problem solving and implement effective solutions
• Exceptional communication skills: articulate and professional at all organizational levels and via all mediums
• Detail oriented with excellent verbal and written communication skills
• Communicates information clearly, ranging from straightforward to detailed, and produces written communications that are well-structured and have minimal errors
• Identifies and suggests areas for improvement and is successful at implementing changes
• Meticulous attention to detail and accuracy

Nice To Haves

• Experience in a growing, professional services/technology environment
• Advanced PowerPoint and Excel skills (storytelling, data visualization, light analytics/dashboards)
• Experience creating EA/ops playbooks and training cross‑coverage support
• Event/onsite logistics expertise, including AV coordination and vendor management
• Familiarity with behavioral frameworks (e.g. DISC) and navigating differing leadership styles

Responsibilities

• Support for three Executives
• Proactively manage complex calendars across time zones; resolve conflicts; create look‑aheads and protect focus/priority blocks. Balance gatekeeping with access—opening time for the most important work while maintaining positive stakeholder experiences.
• Manage email and information flow, flagging priorities and drafting responses or summaries as appropriate.
• Coordinate end‑to‑end travel; prepare detailed itineraries; handle changes and on‑trip support.
• Own expense reporting and reimbursements; ensure timely, accurate submissions and compliance.
• Meeting and event orchestration
• Lead the cadence, agenda design, pre‑reads, materials, logistics, note‑taking, and action tracking for Quarterly Business Reviews, leadership meetings, all‑hands, etc.
• Ensure participants are prepared and outcomes are clear; drive follow‑through on decisions and action items.
• Partner with event coordinator to run on‑site/virtual events, including AV, room setup, catering, and vendor/stakeholder coordination.
• Communications and materials
• Draft, edit, and design high‑quality presentations and documents for QBRs, leadership calls, all‑team communications, and external meetings.
• Conduct research and compile data to inform decision‑making; prepare briefs and talking points.
• Capture meeting notes and distribute concise recaps and action logs.
• Maintain and improve shared systems (Outlook/Teams/SharePoint/OneNote/Planner or equivalent), ensuring visibility and standardization across templates, naming conventions, and workflows.
• Continuous improvement and AI enablement
• Introduce and refine processes that improve efficiency, standardization, and collaboration.
• Use AI tools (e.g., Microsoft Copilot, ChatGPT) to accelerate drafting, summarization, scheduling optimization, data synthesis, and deck/storyline development.
• Discretion, flexibility, and judgment
• Handle sensitive information with the highest integrity.
• Provide after‑hours support for urgent needs with flexibility to rebalance time as appropriate.

Benefits

• Medical, Dental and Vision – Coverage for employees, dependents, and domestic partners.
• Employee Assistance Program (EAP) – Confidential support for personal and work-related challenges.
• 401(k) Plan – Includes a company matching program and profit-sharing contributions.
• Discretionary Bonus Program – Recognizing employee contributions.
• Flexible Spending Accounts (FSA) – Pre-tax savings for dependent care, transportation, and eligible medical expenses.
• Paid Time Off (PTO) – Begins accruing on the first day of work. Full-time employees accrue 15 days per year, and employees working less than full-time accrue PTO on a prorated basis.
• Holidays – A minimum of 10 paid holidays per year.
• Family Building Benefits – Includes adoption and fertility assistance.
• Paid Parental Leave – Up to 12 weeks of paid leave for employees who meet eligibility criteria.
• Life Insurance & AD&D – 100% of premiums covered by Milliman.
• Short-Term and Long-Term Disability – Fully paid by Milliman.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees