Hybrid Executive Assistant – IntelliScript

at Milliman

• Job title: Executive Assistant – IntelliScript
• Job type: Full Time
• Experience level: Senior, Lead
• Salary: $78,800 - $145,130 per year
• Degree requirement: No Education Requirement
• Location requirements: Hybrid, Chicago, United States

About the role

• Executive Assistant delivering comprehensive support to three Executive Leaders at Milliman's IntelliScript. Managing schedules, travel, and communication while enhancing operational efficiency with AI tools.

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.

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.

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.