[Hiring] Chief of Staff @VaVa Virtual Assistants

Role Description

This is an independent contractor (1099) position. VaVa contractors are responsible for managing their own taxes, benefits, and business expenses.

We are looking for a seasoned Chief of Staff who can operate as a true strategic partner to the leaders we serve. This role requires someone capable of thinking at the level of the founder or executive, filtering what deserves their attention, and translating vision into organizational action.

Beyond your client work, you will be part of a contractor community that genuinely invests in one another's success.

Expectations

• Represent VaVa Virtual Assistants in a Positive and Professional Manner
• Operate at a level of professionalism that reflects the trust placed in you by both VaVa and the executives you support.
• Serve as a model for VaVa's values within your client relationships, particularly in high-stakes or sensitive communications.
• Strengthen VaVa's contractor community by bringing a senior leadership perspective to shared spaces and conversations.
• Take Ownership of Client Satisfaction
• Hold ultimate accountability for the health of the client relationship, including how well the engagement is serving their evolving strategic needs.
• Develop deep enough context about the client's priorities and pressures to anticipate what they need before they ask.
• Navigate complex or sensitive challenges with sound judgment, protecting both the quality of service and the integrity of the relationship.
• Monitor engagement scope continuously and initiate proactive conversations with clients when their needs have outgrown or shifted from the current structure.

Responsibilities

• Serve as a trusted strategic partner to the founder or executive, thinking alongside them on decisions, priorities, and organizational direction.
• Filter and manage what reaches the executive's attention, distinguishing between what requires their judgment and what can be handled or delegated.
• Translate the executive's vision and priorities into clear direction for their team, ensuring organizational alignment without requiring the founder to repeat themselves.
• Prepare the executive for high-stakes meetings, presentations, board conversations, and external engagements, including briefings, talking points, and background research.
• Oversee and synthesize reporting from across the business so the executive has an accurate, real-time picture of operations, team performance, and progress toward goals.
• Act as a senior liaison between the executive and internal teams, external stakeholders, partners, and clients, representing their interests with accuracy and discretion.
• Identify strategic gaps, emerging risks, or organizational misalignments and bring them to the executive with context and a recommended path forward.
• Support organizational planning, including quarterly priorities, team structure decisions, and resource allocation conversations.
• Draft and edit high-level communications on behalf of the executive, including board memos, partner correspondence, and internal leadership updates.
• Manage sensitive information spanning personnel, financials, legal matters, and strategic plans with an unwavering commitment to confidentiality.
• Lead or support special projects that require senior-level coordination and fall outside the scope of the existing operational team.
• Maintain awareness of the executive's bandwidth and proactively restructure their commitments when the load becomes unsustainable.
• Collaborate with an OBM or operational team where one exists, ensuring strategic priorities are translating into operational execution.
• Continuously evaluate whether the current engagement structure is serving the executive's evolving needs and initiate conversations to adjust when it is not.

Qualifications

• Must reside and be authorized to work in the United States.
• At least 7 years of demonstrated experience in a senior operational, strategic, or executive-level support role.
• At least 3 years of experience working full-time in a virtual or remote capacity.
• Available at least 20 hours per week to support high-touch (daily), deliverable-focused clients.

Technical Qualifications

• Proficiency in Google Workspace and Microsoft Office, including the ability to create executive-level presentations, briefing documents, and reporting materials.
• Experienced use of Slack and Zoom in a senior coordination and leadership communication capacity.
• Ability to quickly orient within any CRM or project management tool a client is using, extract relevant data, and work fluently within existing systems without requiring onboarding support.
• Experience managing large-scale travel and event logistics as the project lead, including coordinating across multiple vendors, venues, and stakeholders within a single engagement.
• Comfort with strategic planning and visual thinking tools such as Notion, Lucidchart, Loom, or equivalent platforms used to align teams and communicate organizational priorities.
• General AI literacy with the ability to apply AI tools in ways that improve executive output, communication, and decision-making support.

Preferred

• Familiarity with automation tools such as Zapier or equivalent, sufficient to evaluate whether a workflow exists and direct its implementation even if not personally building it.
• Experience working within or alongside financial planning, reporting, or budgeting tools at an organizational level.
• Exposure to board-level or investor-facing documentation, communications, or meeting preparation.

Education

A degree is not required, though candidates at this level often bring one. What matters far more is a demonstrated history of operating in senior-level roles with measurable strategic impact.