Senior Executive Assistant - Private Family

POSITION OVERVIEW

Title: Senior Executive Assistant

Location: Lake Forest, IL (in-office)

POSITION SUMMARY

We are seeking a seasoned and exceptionally organized Senior Executive Assistant to serve as the central hub for a dynamic and fast-paced household led by two high-net-worth individuals. Both principals maintain demanding professional schedules and have full-time Executive Assistants supporting them in their corporate roles. However, their personal and family lives require an additional layer of proactive, strategic support to ensure smooth coordination across all moving pieces.

This role is ideal for someone who thrives on bringing structure to complexity, has a service mindset, and can operate with discretion, professionalism, and emotional intelligence. The Senior Executive Assistant will liaise across household staff, corporate teams, philanthropic stakeholders, and vendors, ensuring that information flows seamlessly and priorities are always clear.

ESSENTIAL DUTIES AND RESPONSIBILITIES

• Manage and coordinate complex personal schedules and travel for principals.
• Ensure seamless integration between personal and professional calendars by working closely with their business EAs.
• Oversee philanthropic board calendars and related logistics, ensuring the principals are prepared for all meetings and commitments.
• Lead regular check-ins with key support staff (Director of Properties, Accountant, etc.) to align on upcoming needs and priorities.

• Serve as the primary liaison across household and external stakeholders; streamlining communication, reducing noise, and surfacing what matters most.
• Provide timely, synthesized updates so both principals stay proactively informed without needing to track details themselves.
• Draft, manage, and organize personal correspondence, documentation, and day-to-day logistics.

• Design and maintain systems for tracking information, priorities, and household operations.
• Coordinate across internal teams—Director of Properties, household staff, finance—to drive clarity, accountability, and follow-through.
• Help shape a proactive and well-aligned support culture that stays ahead of evolving needs.

• Oversee logistics for personal events and complex domestic/international travel.
• Provide occasional support for adult children (e.g., travel planning, appointments).
• Work with vendors and staff to ensure smooth execution of all personal and household commitments.

• Have 7+ years of experience supporting C-level executives, ultra-high-net-worth individuals, or operating in a senior EA or Chief of Staff capacity; ideally within a fast-paced household, family office, or similarly complex environment.
• Connect the Dots: You instinctively synthesize information across people, places, and priorities—aligning moving pieces into a clear, cohesive picture.
• Think Two Steps Ahead: You’re always looking around corners, anticipating what’s needed before it’s asked, and solving problems early.
• Bring Structure to Chaos: You love building systems that make life easier, not just for you, but for everyone around you. From calendar protocols to communication flows, you design smart solutions and follow through.
• Know When to Lead and When to Listen: You’re confident managing up and across, but you know how to stay in sync with evolving preferences and dynamics especially within a family environment.
• Operate with Discretion and Care: You understand the nuanced boundaries of working in someone’s home and life. You’re respectful of privacy, grounded in professionalism, and unshakably discreet.
• Build Trust Quickly: Your follow-through, calm demeanor, and thoughtful communication style make you someone others can count on, whether it’s a housekeeper, property manager, or principal.
• Care About the Bigger Picture: You bring a genuine interest in philanthropy and purpose-driven work. Whether through past roles, volunteer efforts, or personal passion, you understand the values behind giving and are motivated by impact. Experience supporting philanthropic initiatives or nonprofit organizations is a strong plus.

SALARY

$175,000 - $250,000

DIVERSITY, EQUITY, AND INCLUSION

We know that innovation thrives on teams where diverse points of view come together to solve hard problems.  As such, we explicitly seek people that bring diverse life experiences, diverse educational backgrounds, diverse cultures, and diverse work experiences.  Please be prepared to share with us how your perspective will bring something unique and valuable to our team.