Executive & Personal Assistant to Co-CEOs

Wheelhouse is seeking an experienced, highly organized Executive & Personal Assistant to support our two Co-CEOs in a fast-paced commercial real estate development company. This is a unique opportunity to become a trusted partner to two executives with distinct leadership styles. The role requires exceptional professionalism, flexibility, sound judgment, discretion, and the ability to create order in a dynamic environment. This position extends beyond traditional executive support.

The successful candidate will provide seamless assistance across both business and personal matters, helping the Co-CEOs stay focused on leadership, decision-making, key relationships, and the highest-value priorities of the organization. This role requires an individual of unquestionable integrity
. Trust, discretion, and professional maturity are essential, as you will have access to confidential business strategies, financial information, client and partner relationships, personal matters, and other highly sensitive information.

• Manage complex and constantly changing executive calendars, protecting time, priorities, and focus.
• Coordinate domestic and international travel, including detailed itineraries and last-minute changes.
• Prioritize competing requests and adjust schedules as needs change.
• Prepare correspondence, reports, presentations, meeting materials, and confidential documents.
• Serve as a primary point of contact for internal leadership, employees, clients, vendors, and external partners.
• Coordinate meetings, events, and executive logistics.
• Manage confidential business information and sensitive client, partner, and internal communications.
• Assist with personal scheduling, appointments, household coordination, and personal financial administration.
• Coordinate with vendors, contractors, service providers, and family contacts on behalf of the executives.
• Manage multiple high-priority projects, details, and deadlines with minimal oversight.
• Identify issues early, solve problems proactively, and ensure strong follow-through.
• Maintain strict confidentiality in all business and personal matters.

• Executive assistant experience supporting senior executives, founders, business owners, or high-performing leadership teams.
• Personal assistant experience or comfort supporting both business and personal responsibilities.
• Exceptional organizational, scheduling, and calendar management skills.
• Outstanding written and verbal communication abilities.
• Advanced proficiency with Microsoft Office and modern business technology.
• Strong judgment and decision-making ability.
• High emotional intelligence and exceptional interpersonal skills.
• Ability to remain composed under pressure while adapting quickly to changing priorities.
• Experience handling confidential financial, business, and personal information.
• A proactive, service-minded approach with a high degree of ownership and follow-through.

• Notices what needs to be done, takes initiative, and follows through without waiting for constant direction.
• Protects confidential information and communicates with professionalism, judgment, and discretion.
• Engages colleagues, clients, partners, vendors, and family members with empathy, respect, and a warm, professional presence that reflects our culture.
• Is exceptionally organized, detail-oriented, and able to keep multiple priorities moving at once.
• Thrives in a fast-paced, entrepreneurial environment where plans can change quickly.
• Adapts your communication and work style to effectively support two executives with different personalities and leadership styles.
• Is resourceful, calm under pressure, and solutions-oriented.
• Builds trust quickly with executives, employees,…