Key Responsibilities and Required Skills for a Head Assistant

🎯 Role Definition

The Head Assistant is far more than a traditional support role; it is a strategic and operational linchpin for a senior executive and their wider department. This individual acts as a trusted right-hand and force multiplier, enabling the executive to focus on high-level strategic initiatives by flawlessly managing the operational and administrative complexities of their office. The Head Assistant serves as a primary gatekeeper, a project manager for key initiatives, and often a leader and mentor to other administrative staff. They operate with a high degree of autonomy, anticipate needs before they arise, and handle sensitive information with the utmost discretion, making them an indispensable partner in driving organizational effectiveness.

📈 Career Progression

Typical Career Path

Entry Point From:

Senior Executive Assistant
Executive Business Partner
Senior Office Manager with EA duties
Project Coordinator

Advancement To:

Chief of Staff
Director of Administration / Business Operations
Senior Project Manager
Business Operations Manager

Lateral Moves:

Senior Project Manager
Operations Manager
Executive Communications Manager

Core Responsibilities

Primary Functions

Execute intricate and dynamic calendar management, strategically scheduling and prioritizing meetings, appointments, and events across multiple time zones while safeguarding the executive's time for strategic work.
Orchestrate complex domestic and international travel arrangements from end to end, including flights, accommodations, ground transportation, and detailed itineraries that account for contingencies.
Serve as the primary point of contact and gatekeeper for the executive's office, professionally fielding, screening, and directing all internal and external communications with diplomacy and tact.
Prepare, proofread, and format high-stakes internal and external communications, including confidential correspondence, board materials, and client-facing presentations, ensuring accuracy and brand consistency.
Act as a key liaison between the executive and other senior leaders, board members, clients, and key stakeholders, fostering strong relationships and ensuring seamless communication flow.
Plan and execute critical meetings, leadership off-sites, and company-wide events, managing all logistics from agenda creation and venue selection to catering and post-event follow-up.
Drive key special projects on behalf of the executive, from initial research and planning through execution and completion, ensuring objectives are met on time and within budget.
Attend important meetings to capture detailed notes, summarize key takeaways, and diligently track action items to ensure accountability and project momentum.
Provide leadership, mentorship, and guidance to a team of administrative assistants, delegating tasks, fostering professional development, and promoting a collaborative support environment.
Anticipate the needs of the executive by proactively identifying potential conflicts, solving logistical challenges, and providing necessary materials well in advance of deadlines.
Handle highly confidential and sensitive corporate, financial, and personal information with unwavering discretion and a deep understanding of its implications.
Manage and reconcile complex expense reports, monitor departmental budgets, and process invoices, ensuring compliance with company financial policies.
Develop a deep understanding of the business and its key priorities to make informed, independent decisions that align with the executive's goals and preferences.
Build and maintain a robust network of internal and external professional relationships to facilitate collaboration and efficient problem-solving across the organization.

Secondary Functions

Support ad-hoc data requests and exploratory data analysis by gathering information, conducting preliminary research, and summarizing findings to support executive decision-making.
Contribute to the organization's administrative strategy by identifying inefficiencies and recommending process improvements for scheduling, communication, and office operations.
Collaborate with business units such as HR, Finance, and IT to streamline departmental administrative processes, assist with new hire onboarding, and ensure policy adherence.
Participate in sprint planning and agile ceremonies within the executive's leadership team, helping to track project milestones and maintain organizational alignment.
Manage relationships with key vendors, including negotiating contracts for services, supplies, and events, and ensuring quality of service.
Take ownership of office management responsibilities for the executive suite or department, ensuring a professional and productive work environment.
Assist in the preparation of annual budgets and forecasts by compiling historical data and tracking departmental spending against financial targets.
Champion and drive initiatives aimed at boosting team morale, recognition, and culture within the executive's department.

Required Skills & Competencies

Hard Skills (Technical)

Complete mastery of Microsoft Office Suite (Outlook, PowerPoint, Excel, Word, Teams) and Google Workspace, with the ability to create sophisticated documents and presentations.
Deep proficiency with modern travel and expense management software (e.g., Concur, TripActions, Expensify) for seamless booking and reconciliation.
Hands-on experience with project management and collaboration tools (e.g., Asana, Trello, Slack, Monday.com) to track tasks and coordinate team efforts.
Advanced digital calendaring skills, demonstrating the ability to manage complex schedules for multiple principals across different platforms and time zones.
Strong technical aptitude and the ability to quickly learn and master new software, applications, and internal company systems.

Soft Skills

Unwavering discretion and sound judgment, with a proven track record of handling highly sensitive and confidential information.
Exceptional emotional intelligence and interpersonal skills, capable of building rapport and navigating complex relationships with poise and professionalism.
A proactive, forward-thinking mindset with the ability to anticipate needs and solve problems before they escalate.
Superior organizational and time-management skills, with a meticulous attention to detail and the ability to manage multiple competing priorities without sacrificing quality.
Polished and articulate communication skills, both written and verbal, with the ability to draft correspondence on behalf of an executive.
Remarkable resilience, grace under pressure, and the ability to thrive in a fast-paced, ambiguous, and constantly changing environment.
Resourcefulness and an ownership mentality, with the ability to operate with a high level of autonomy and find creative solutions to challenges.
Natural leadership and mentorship capabilities, with a desire to guide and develop junior administrative professionals.
A strong sense of urgency combined with a calm and confident demeanor.
A collaborative spirit and a "no task is too small" attitude, demonstrating a commitment to the team's success.

Education & Experience

Educational Background

Minimum Education:

Bachelor's Degree or equivalent practical experience in a high-level administrative capacity.

Preferred Education:

Bachelor’s or Master’s Degree in a relevant field.

Relevant Fields of Study:

Business Administration
Communications
Project Management

Experience Requirements

Typical Experience Range: 8-15+ years of progressive experience in an executive support role.

Preferred: Demonstrable experience supporting a C-level executive, Founder, or Head of a major business unit within a fast-paced corporate, tech, or high-growth environment. Prior experience formally or informally managing other administrative staff is highly desirable.