Manager, Senior Executive Assistant to the CEO

Core Spaces•Chicago, IL

23d•Hybrid

About The Position

Core Spaces is seeking an exceptional Executive & Personal Assistant to support the Founder/CEO. This role is designed to bring organization, anticipation, thoughtfulness, and follow-through to a demanding professional and personal life. It goes beyond basic calendar management, acting as a trusted 'quarterback' to anticipate needs, manage numerous details, and ensure important tasks are completed. The primary goal is to reduce the CEO's mental load, freeing up time and energy for critical activities. This highly trusted position offers high-level support and operational leverage, coordinating closely with various resources to ensure seamless operations across professional, personal, family, and social commitments. The ideal candidate thrives in a fast-paced, dynamic environment and understands the privacy and service expectations associated with supporting a high-profile principal.

Requirements

Ten or more years of experience providing high-level support to a CEO, founder, high-profile principal, or comparable senior executive in a fast-paced and highly confidential environment.
Strongly preferred experience supporting an entrepreneur, athlete, entertainer, high-net-worth individual, family office, or private office where professional and personal schedules must be understood together.
Demonstrated success managing exceptionally complex calendars, frequent changes, professional travel, private aviation, and high-level stakeholders.
Experience directly supervising, coaching, or directing another administrative, executive-services, concierge, or project-support professional.
Exceptional judgment, emotional intelligence, discretion, resilience, and executive presence.
A track record of anticipating needs, making sound routine decisions with limited direction, and discerning when a matter genuinely requires the principal's input.
A high-touch service orientation paired with the confidence to push back, resolve ambiguity, and protect the executive from unnecessary decisions.
Outstanding written communication, organization, prioritization, and attention to detail.
Advanced proficiency with Google Workspace and Microsoft Office and the ability to quickly learn calendar, travel, expense, communication, and workflow platforms.
The ability to remain calm, constructive, and adaptable when priorities change repeatedly or instructions are incomplete.
The maturity and stamina to work within a demanding, highly visible environment without becoming rattled, defensive, or dependent on constant reassurance.

Nice To Haves

Supporting a founder, entrepreneur, athlete, celebrity, high-net-worth individual, or other principal whose professional and personal schedules must be coordinated holistically.
Working within a family-office, private-office, real estate, investment, development, hospitality, or similarly relationship-driven environment.
Coordinating private aviation, international travel, multiple properties, high-touch events, or complex personal and professional ecosystems.
Building trust with family members, personal staff, business leaders, external partners, and administrative teams while protecting clear boundaries and confidentiality.
Creating order and momentum around an executive who operates quickly, changes direction frequently, and expects proactive problem-solving.

Responsibilities

Own and thoughtfully manage a complex professional and personal calendar, understanding priorities, protecting time, and proactively solving scheduling conflicts.
Coordinate meetings, appointments, dinners, family commitments, school and sporting events, travel, workouts, and personal obligations.
Make informed judgments about scheduling, prioritizing, and delegating tasks to optimize time usage.
Protect focus time and minimize calendar clutter.
Ensure each day is organized to reduce friction and unnecessary transitions, accounting for travel, meals, preparation, and competing obligations.
Provide timely reminders, context, and updates to the CEO and stakeholders regarding schedule changes.
Develop a deep understanding of the CEO’s relationships, commitments, preferences, and decision-making rules to ensure accurate scheduling.
Manage all aspects of travel logistics, from planning and booking to real-time monitoring and independent resolution of disruptions.
Coordinate private aviation arrangements for the CEO and other Core business travelers.
Partner with Finance, Accounting, and personal/family office resources on travel-related contracts, billing, and expense reconciliation.
Coordinate birthdays, anniversaries, milestones, celebrations, and other important life events for key relationships.
Manage gifts and thoughtful gestures, including brainstorming, sourcing, purchasing, packaging, shipping, and confirming delivery.
Maintain systems to track important people, moments, preferences, addresses, budgets, and deadlines for thoughtful gestures.
Manage household-related coordination, special purchases, deliveries, and service appointments.
Oversee renewals, memberships, personal paperwork, and other administrative tasks.
Serve as a communication and coordination hub across the family office and personal support ecosystem, ensuring clear communication and follow-up.
Coordinate with accountants, attorneys, household staff, property managers, vendors, and advisors.
Act as the primary intake and coordination point for professional and personal requests requiring the CEO’s attention.
Establish clear assignments, deadlines, and escalation protocols with internal partners and personal support resources.
Maintain visibility into coordinated work, risks, costs, and schedule implications.
Track outstanding requests, deadlines, and projects, surfacing issues requiring the principal’s attention.
Provide macro-level oversight and coordination for residences, ensuring issues are surfaced and projects progress.
Build documented processes and a reliable coverage model for travel and periods of limited availability.
Ensure proper preparation for important meetings and events, including objectives, attendee context, briefing materials, and talking points.
Communicate professionally on behalf of the CEO when authorized, maintaining his voice and credibility.
Capture and track commitments, decisions, and follow-up actions.
Protect highly confidential business, financial, legal, and personal information with absolute discretion.
Coordinate logistics, attendees, materials, food, transportation, and follow-up for various events.
Partner with internal teams and external stakeholders on event logistics, vendor quotes, budgets, and special requests.
Make routine administrative and logistical decisions independently based on the CEO’s preferences and priorities.
Translate incomplete or fast-moving direction into executable steps.
Coordinate and delegate defined work to designated support resources, maintaining clear ownership.
Develop systems, templates, and workflows to improve efficiency.
Maintain organized contacts, vendor records, budgets, project files, and process instructions.
Utilize technology, automation, and AI-enabled tools to reduce administrative burden.
Provide ongoing support to other executives through collaboration on major company events or shared priorities.
Perform other related duties and special projects as assigned.
Complete all physical requirements of the role with or without reasonable accommodation.

Benefits

A culture that provides you with a sense of belonging
Hybrid or remote work options may vary by role to support work-life balance
Competitive pay that values your contributions
Incentives designed to reward your achievements
Paid flexible PTO to disconnect or celebrate life milestones
Paid 14+ holidays, including your birthday, to disconnect and celebrate
Paid Parental Leave that begins after 90 days
Paid volunteer time off to give back to your community
Monthly workshop weeks; fewer meetings & more collaboration
Robust health plan options that begin within at least 30 days of your employment
Monthly phone reimbursement
Wellness allowance and perks, including a yearly subscription to a meditation app
An environment that provides you a voice to share your perspectives
Employee Assistance Program (EAP) for access to confidential support services
Company retirement options including 401(k) + matching & Roth account option