Executive Assistant
About the Opportunity
Our client is a well-funded, mission-driven organization focused on driving large-scale social impact through culture, strategy, and innovation. Backed by an exceptional leadership team and a network of influential partners, the organization is building something ambitious and is looking for an Executive Assistant who thrives in a fast-paced, high-performing environment.
The Role
We are seeking an experienced Executive Assistant (5–10 years) to support the Chief Strategy Officer. This role exists to maximize executive effectiveness. The Chief Strategy Officer's highest-value work centers on shaping strategy, aligning senior leaders, building an exceptional team, and cultivating key internal and external relationships. The Executive Assistant serves as a true strategic partner, creating the structure, focus, and operational rhythm that enables the executive to perform at their highest level.
This is far more than calendar management. It is about protecting executive attention—preserving time for strategic thinking, leadership meetings, hiring, and deep work while anticipating needs before they arise. The ideal candidate builds trusted partnerships through sound judgment, discretion, proactive communication, and thoughtful problem-solving.
This is a remote position based in Chicago operating primarily on East Coast hours. The executive is based in Chicago, so occasional flexibility for Central Time coverage is appreciated
Key Responsibilities
Executive Calendar & Priority Management
- Own a complex, high-volume executive calendar, ensuring it reflects strategic priorities rather than simply accommodating requests.
- Thoughtfully structure meeting schedules to preserve time for strategic work, leadership priorities, and personal well-being.
- Prioritize, reschedule, and push back on meeting requests when appropriate while managing frequent changes across multiple time zones
Inbox & Communications Management
- Manage a high-volume executive inbox by triaging, flagging priorities, drafting communications, and tracking follow-up items.
- Anticipate needs, monitor commitments, and proactively reduce administrative burden.
Executive Operations
- Coordinate internal and external meetings, ensuring agendas, materials, logistics, and participants are aligned.
- Track action items and drive follow-through on key initiatives.
- Coordinate travel, expense reporting, and day-to-day operational support.
- Provide occasional personal assistance, including reservations, appointments, gifts, family logistics, and personal travel planning.
Stakeholder Management
- Handle highly confidential information with the utmost discretion.
- Build strong working relationships with senior leaders, board members, and external partners.
- Exercise sound judgment, communicate candidly and professionally, and serve as a trusted point of coordination across the organization.
What Success Looks Like
After the first year, the Executive Assistant will have
- Built a highly trusted partnership with the Chief Strategy Officer.
- Created a calendar that protects strategic priorities and uninterrupted focus time.
- Eliminated unnecessary inbox and administrative burden.
- Enabled the executive to spend the majority of their time focused on strategy, leadership, hiring, and external relationships.
- Established systems and rhythms that increase efficiency, organization, and executive effectiveness.
Qualifications
- 5–10 years of Executive Assistant experience supporting senior executives, ideally in a dedicated one-to-one partnership.
- Exceptional calendar management skills with a strong instinct for protecting executive time and attention.
- Demonstrated ability to handle confidential information with professionalism and discretion.
- Proactive, resourceful, and comfortable exercising judgment independently.
- Strong communication skills with the confidence to respectfully challenge priorities when appropriate.
- Highly organized, detail-oriented, and able to thrive in fast-moving, entrepreneurial environments.
- Warm, polished, collaborative, and relationship-oriented.
- Comfortable working remotely on East Coast hours with occasional flexibility for Central Time coverage.
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