Executive Assistant

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

Benefits offered by this job

End-of-year bonus

Job summary

Career Group is seeking a proactive Executive Assistant to the CEO for a founder-led strategic advisory firm and venture fund. The role is primarily remote with occasional visits to Pennsylvania and travel alongside the CEO, serving as a trusted partner across professional and personal responsibilities.

You will manage a complex calendar and inbox, plan domestic and international travel, draft communications, and coordinate events while maintaining utmost discretion and high judgment in a

Qualifications

• Experience supporting a founder or senior executive in a fast-paced environment.
• Ability to anticipate needs and drive tasks to completion.
• Strong calendar management and travel coordination skills.
• Excellent written and verbal communication across internal and external stakeholders.
• Ability to handle confidential information with discretion.

Responsibilities

• Manage a complex calendar spanning business engagements, investor relationships, and family commitments.
• Draft polished communications reflecting the CEO’s voice.
• Plan domestic and international travel with detailed itineraries and real-time problem solving.
• Prepare meeting briefs and background materials for decision-making.
• Coordinate speaking engagements, events, and family logistics as needed.
• Maintain organized records across email, Slack, and calendar platforms.

Skills

Proactive

Discretion

Communication

Organization

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