Manager, Senior Executive Assistant to the CEO

Position Overview

The purpose of this role is simple:

Make life easier. Create space. Help life slow down.

Core Spaces is looking for an exceptional Executive & Personal Assistant who can bring organization, anticipation, thoughtfulness, and follow-through to a very full professional and personal life.

This is far more than a calendar-management role. The right person will become a trusted quarterback-someone who understands what matters, anticipates needs before they become tasks, keeps dozens of moving pieces organized, and makes sure important things don't fall through the cracks.

Success means fewer things to remember, fewer things to chase, fewer unnecessary decisions, and more time and energy available for the things that actually matter.

This highly trusted role provides high-level support and operational leverage to the Founder/CEO and serves as his primary point of coordination across professional, personal, family, and social commitments. The role owns executive and personal support and coordinates closely with designated resources to prevent conflicts and create seamless handoffs.

This position is dedicated to supporting the CEO and is best suited for someone who thrives in a fast-moving, frequently changing environment and understands the privacy and service expectations associated with supporting a high-profile principal.

What You Will Do

Calendar Time and Priority Management

Own and thoughtfully manage a complex professional and personal calendar. This isn't just booking meetings. It means understanding priorities, protecting time, recognizing conflicts before they happen, and helping create a calendar that reflects how time should actually be spent.

• Coordinate meetings, appointments, dinners, family commitments, school and sporting events, travel, workouts, and personal obligations.
• Understand what is truly important versus what can wait, and use that judgment to determine what should be scheduled, moved, declined, shortened, or delegated.
• Protect focus time and avoid unnecessary calendar clutter.
• Anticipate scheduling conflicts and solve them proactively, including frequent rescheduling and short-notice changes.
• Make sure each day is organized in a way that reduces friction and unnecessary transitions, accounting for travel time, meals, preparation, delays, and competing obligations.
• Keep the CEO oriented throughout the day with timely reminders, context, and clear updates to him and affected stakeholders as plans change.
• Build a working knowledge of the CEO's priority relationships, immovable commitments, preferences, routines, and decision-making rules so scheduling choices become increasingly independent and accurate.

Travel Coordination

Own travel logistics from beginning to end. The goal is for travel to feel effortless. The right person thinks beyond just making reservations: What does the entire journey look like? What could go wrong? What needs to happen before departure? What would make the experience better?

• Plan and coordinate professional, personal, and family travel, including private and commercial aviation, international and multi-city itineraries, ground transportation, lodging, and short-notice changes.
• Manage private aviation arrangements for the CEO and designated Core business travelers, including vendor communication, flight sourcing, booking, passenger details, and contingency planning.
• Monitor travel in real time and independently resolve delays, cancellations, rebooking needs, food and hospitality requirements, and other disruptions.
• Partner with Finance, Accounting, and appropriate personal or family-office resources on travel-related contracts, billing, wire transactions, vendor payments, expense reconciliation, and documentation.

Thoughtfulness & Leadership Support

Help turn good intentions into action. Relationships matter enormously, but a busy life makes it easy to think, "I should do something for that person," and then move on to the next thing. This person helps make sure those moments don't disappear. The objective isn't just remembering birthdays. It's helping someone be a more thoughtful leader, friend, family member, and partner.

• Coordinating birthdays, anniversaries, milestones, celebrations, weddings, new babies, condolences, get-well wishes, holidays, and important life events.
• Managing gifts and thoughtful gestures, from brainstorming creative ways to recognize employees, friends, partners, and family to sourcing, purchasing, packaging, shipping, and confirming delivery.
• Keeping track of important people and moments, including recipient preferences, addresses, budgets, approvals, and delivery deadlines.
• Turning ideas into execution and maintaining systems that ensure important relationships receive the attention they deserve.
• Coordinating Core gear, swag, and custom items with Marketing and other internal partners to maintain brand standards and avoid duplicative gifting or merchandise processes.
• Managing vendors and resolving routine inventory, shipping, and delivery issues so thoughtful gestures arrive as intended.

Personal Life Administration

Own many of the small but important things that create unnecessary mental load. The goal is to create a trusted system so there is confidence that if something needs to happen, someone has it.

Examples include:

• Bills and important deadlines.
• Returns and exchanges.
• Reservations.
• Household-related coordination, special purchases, deliveries, and service appointments.
• Renewals and memberships.
• Personal paperwork.
• Reminders and follow-through.
• Other miscellaneous personal-assistant responsibilities and special projects.

Family Office Quarterback

Serve as a communication and coordination hub across the family office and personal support ecosystem. This does not mean doing everyone's job. It means knowing who owns what, making sure communication is clear, following up when necessary, and ensuring responsibilities don't fall between people.

• Coordinate with accountants, attorneys, household staff, property managers, vendors, advisors, and other members of the broader family-office team.
• Serve as the primary intake and coordination point for professional and personal requests requiring the CEO's time, attention, approval, or support resources.
• Establish clear assignments, deadlines, decision authority, service expectations, and escalation protocols across internal partners and personal-support resources.
• Maintain visibility into coordinated work, risks, costs, and schedule implications without requiring the CEO to manage each handoff.
• Keep track of outstanding requests, important deadlines, and projects, surfacing issues and decisions that require the principal's attention.
• Over time, provide macro-level oversight and coordination with property managers for residences in Chicago and Lake Geneva-ensuring issues are surfaced, responsibilities are clear, projects are progressing, and the principal doesn't need to personally manage every detail.
• Build documented processes and a reliable coverage model for travel, leave, and periods of limited availability.

Executive Preparation and Communication

• Ensure the right preparation happens before important meetings and events, including clear objectives, attendee context, briefing materials, talking points, and timely reminders.
• Communicate professionally on behalf of the CEO when authorized, maintaining his voice, credibility, and relationship priorities.
• Capture and track commitments, decisions, follow-up actions, and deadlines while keeping business ownership with the appropriate leaders.
• Protect highly confidential business, financial, legal, people, family, and personal information with absolute discretion.

Events Relationships and Special Requests

For important meetings and events, begin with one question: What does success look like? Then help make sure everything required to achieve that outcome happens. The expectation is not that an event happens. It's that it happens well.

• This may include company meetings, investor and partner dinners, site tours, leadership events and offsites, family events, celebrations, trips, YPO activities, philanthropic initiatives, or gatherings.
• Responsibilities could include coordinating logistics, attendees, materials, food, transportation, follow-up, gifts, and other details-but more importantly, thinking about the experience as a whole.
• Partner with Events, Marketing, Office Services, Finance, other Executive Assistants, and external stakeholders on logistics and execution, including vendor quotes, budgets, payment documentation, supplies, and special requests.
• Own or delegate event-related gifting, swag, special-event items, and high-touch stakeholder requests that bring thoughtfulness to company culture through meaningful recognition, gestures, and experiences, remaining accountable for timing, quality, and follow-through.
• Collaborate with the broader administrative team on major Core events and shared executive priorities while remaining dedicated to the CEO's needs.

Judgment Delegation and Operational Excellence

• Make routine administrative and logistical decisions independently using an understanding of the CEO's preferences, priorities, and decision-making guardrails.
• Translate incomplete or fast-moving direction into executable next steps, asking focused questions only when the outcome materially depends on the CEO's decision.
• Coordinate and delegate defined work to designated personal and administrative support resources, maintaining clear ownership and avoiding duplicate requests to the CEO.
• Develop systems, templates, and workflows that improve calendar accuracy, information flow, preparation, travel coordination, and follow-through.
• Keep organized contacts, vendor records, budgets, payment documentation, project files, and recurring-process instructions.
• Use technology, automation, and AI-enabled tools thoughtfully to reduce recurring administrative burden.

Other

• This role is dedicated to supporting the Chief Executive Officer and will provide ongoing support to other executives through collaboration on major company events or shared priorities.
• Occasional travel may be required based on business needs.
• Perform other related duties and special projects as assigned.
• Complete all physical requirements of the role with or without reasonable accommodation.

What Success Looks Like

• The CEO has one reliable point of coordination and is no longer required to reconcile competing instructions or overlapping support resources.
• Professional and personal commitments are evaluated together, and avoidable double- or triple-booking is eliminated.
• Calendar changes, delays, and conflicts are addressed early and communicated clearly.
• The CEO is prepared for important meetings, travel, and stakeholder engagements with minimal administrative interruption.
• Routine decisions are made thoughtfully without repeatedly returning minor choices to the CEO.
• Personal-support resources, Executive Assistants, and internal partners experience clear ownership and effective handoffs.
• The CEO trusts this person to anticipate needs, protect time, exercise judgment, and represent him and Core with professionalism and discretion.

The Person