Executive Assistant

Career Group; Pennsylvania; Hybrid; USD 120,000 - 200,000; Full time

Benefits offered by this job

End-of-year bonus

401(k) with company match

Unlimited PTO

Job summary

Career Group is seeking an Executive Assistant to the CEO, offering a primarily remote role with occasional onsite visits to Pennsylvania. You will manage a high-volume calendar, draft communications, coordinate travel, and support both professional and personal priorities for a high-profile CEO in tech, VC, and media.

The role requires proactive, discreet, and autonomous work in a fast-paced environment, with responsibilities spanning travel, investor communications, and family logistics.

Qualifications

• Experience supporting a founder or senior executive in a fast-paced environment.
• Strong calendar management, travel planning, and prioritization skills.
• Excellent written and verbal communication with high discretion.

Responsibilities

• Manage a high-volume, complex calendar including business, investor, and family commitments.
• Prepare briefs, draft communications, and track deadlines and tasks across channels.
• Coordinate domestic and international travel with detailed itineraries and real-time adjustments.
• Serve as CEO liaison, handling confidential information with discretion and warmth.
• Plan speaking engagements, events, and household logistics in alignment with priorities.
• Develop systems for tracking commitments across email, Slack, text, and calendar.

Skills

Proactivity

Discretion

Communication

Organization

Time management

Tools

Notion

Slack

Google Workspace

AI tools

Job description

Executive Assistant to the CEO | Primarily Remote | $120,000–$200,000

A founder-led strategic advisory firm and venture fund is seeking a highly proactive, resourceful, and discreet Executive Assistant to serve as the CEO’s trusted partner across both professional and personal responsibilities. Working closely with a high-profile CEO in technology, venture capital, media, and investing, this individual will manage a complex calendar, communications, travel, events, and household logistics while helping keep priorities and projects moving forward. This is an excellent opportunity for a high-agency professional who thrives in a fast-paced, high-trust environment, exercises exceptional judgment, and anticipates needs before they arise. The role is primarily remote, with occasional visits to Pennsylvania and travel alongside the CEO.

What You’ll Do

• Manage a high-volume, complex calendar spanning business engagements, investor relationships, media commitments, writing projects, and family responsibilities.
• Anticipate scheduling conflicts, protect high-priority work and personal time, and adjust plans independently as priorities change.
• Manage a high-volume inbox, prioritize incoming requests, draft communications, and ensure important matters receive timely attention.
• Prepare meeting briefs, background materials, and concise notes outlining key objectives, decisions, and follow-up items.
• Track upcoming commitments, deadlines, and outstanding tasks across professional and personal responsibilities.
• Serve as a trusted extension of the CEO, learning working style, preferences, relationships, and priorities to anticipate needs and act on their behalf.
• Act as the primary point of contact for founders, investors, executive assistants, chiefs of staff, and internal team members, representing the CEO with professionalism and warmth.
• Draft polished communications that reflect the CEO’s voice and suit the audience and relationship.
• Plan and coordinate domestic and international travel for the CEO and her family, including flights, accommodations, ground transportation, and detailed itineraries.
• Monitor travel arrangements in real time and quickly resolve disruptions, rebookings, and last-minute changes.
• Coordinate speaking engagements, private dinners, executive gatherings, and family events.
• Manage family schedules, appointments, childcare coverage, and school and activity calendars alongside professional commitments.
• Coordinate household projects, vendors, deliveries, and errands, including regular onsite visits to Mechanicsburg several times per month.
• Travel with the CEO occasionally to support important meetings, engagements, and events.
• Coordinate across the team to communicate decisions, track deliverables, and ensure the CEO’s priorities move forward.
• Develop and maintain efficient systems for tracking commitments, requests, and follow-ups across email, Slack, text, and calendar platforms.
• Identify opportunities to streamline administrative processes and improve information flow.
• Partner with finance, accounting, and legal professionals on invoices, payments, and documentation while maintaining organized, secure business and personal records.
• Handle sensitive business, investment, and family matters with the highest level of discretion and confidentiality.

What We’re Looking For

• Experience supporting a founder or senior executive in a fast-paced, high-standard environment, or experience in hospitality, events, startups, finance, politics, or a related field.
• Highly proactive and resourceful, with the ability to anticipate needs, take initiative, and independently drive tasks through completion.
• Demonstrated experience managing complex calendars, demanding travel arrangements, and competing priorities.
• Comfortable balancing professional and personal responsibilities with equal attention to detail and care.
• Exceptional judgment, with the ability to determine when to act independently, make recommendations, or seek guidance.
• Strong written and verbal communication skills, with the ability to interact professionally with influential founders, investors, and senior executives.
• Highly organized, with exceptional attention to detail and reliable follow-through across multiple overlapping priorities.
• Calm, adaptable, and solutions-oriented when plans change or unexpected issues arise.
• Comfortable working across time zones and maintaining flexibility outside traditional business hours when important matters require attention.
• Receptive to direct, candid feedback and committed to continuous improvement.
• Proficient with Notion, Slack, Google Workspace, and AI tools.
• Exceptional discretion and integrity when handling confidential business, financial, and personal information.
• Comfortable working in a small, fast-moving team where priorities evolve quickly and a high degree of ownership is expected.

Schedule & Location

• Full-time, primarily remote, with occasional onsite visits to Pennsylvania.
• Candidates located within approximately 1–2 hours of Pennsylvania are preferred to accommodate regular onsite needs.
• Occasional travel with the CEO to support key meetings and events is also required.

$120,000–$200,000 annually, depending on experience and qualifications.

• Eligible for an end-of-year bonus after one year
• 401(k) with company match
• Unlimited PTO with advance notice

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