You are the operational counterpart to the CEO.
The CEO generates opportunities, ideas, initiatives, partnerships, and direction. Your job is to convert those inputs into ownership, timelines, accountability, execution plans, and measurable progress.
You will sit at the center of priorities, projects, decisions, and communication. When direction is unclear, you create clarity. When ownership is missing, you identify it. When commitments are made, you ensure they are tracked through completion.
This role combines elements of Executive Assistant, Chief of Staff, Project Manager, and Operations Partner, but the primary function is execution.
You will regularly make judgment calls about what deserves CEO attention, what should be delegated, and what should be deprioritized.
This role is not for candidates who need daily direction, wait for perfect instructions, or are uncomfortable pushing back on senior leadership when execution risks exist.
Core Responsibilities
Act as the first operational filter for incoming requests, opportunities, decisions, and interruptions before they reach the CEO.
When new requests enter the CEO's inbox, calendar, or communication channels:
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Determine whether the CEO must be involved
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Identify items that can be delegated
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Flag items that should be postponed
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Recommend items that should be declined
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Protect executive focus by preventing unnecessary involvement
When priorities conflict, surface recommendations instead of simply presenting problems.
Project Execution
When the CEO introduces a new initiative, partnership, idea, or strategic priority:
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Convert it into a documented execution plan
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Define objectives and desired outcomes
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Assign ownership
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Establish timelines and milestones
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Define success metrics
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Determine immediate next actions
Maintain visibility from project launch through completion.
Follow up proactively when deadlines slip, ownership becomes unclear, or momentum stalls.
Meeting Management
Before executive and leadership meetings:
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Prepare briefing documents
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Gather relevant background information
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Identify risks and unresolved decisions
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Present recommended actions
During meetings:
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Capture decisions in real time
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Document commitments and ownership
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Record action items requiring follow-through
After meetings:
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Distribute action items
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Confirm ownership
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Track completion
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Follow up until commitments are executed
If decisions are made without clear owners, resolve the ambiguity immediately.
Leadership Accountability
Maintain a single source of truth for active initiatives.
Track:
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Deliverables
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Deadlines
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Risks
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Escalations
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Bottlenecks
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Ownership
Provide weekly executive reporting that highlights:
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Progress
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Risks
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Missed commitments
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Decisions requiring executive input
Escalate execution risks before they become operational problems.
Communication Management
Draft and manage:
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Leadership updates
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Internal communications
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Meeting summaries
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Follow-up messages
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Strategic announcements
Translate CEO direction into communication that teams can execute without requiring repeated clarification.
Decision Tracking
Maintain a CEO Decision Log.
For every significant decision:
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Document the decision
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Capture why it was made
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Record ownership
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Track execution status
Prevent repeated discussions caused by missing documentation or unclear accountability.
Organizational Clarity
Identify situations where:
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Ownership is unclear
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Multiple leaders believe they own the same initiative
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Priorities compete for the same resources
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Teams are overcommitted
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Strategic direction is being interpreted differently across departments
Escalate issues with recommended solutions rather than observations alone.
Requirements
Requirements (Non-Negotiable)
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5+ years supporting founders, CEOs, executives, or business owners
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Strong project management experience across multiple concurrent initiatives
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Experience coordinating work across multiple departments
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Exceptional written English
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Experience creating executive reports and operational updates
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Experience documenting processes, systems, and workflows
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Strong organizational systems thinking
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Ability to manage competing priorities without constant supervision
You must be comfortable:
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Making decisions with incomplete information
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Following up repeatedly when accountability is weak
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Challenging assumptions respectfully
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Managing founder-driven environments with frequent changes
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Operating independently for extended periods without detailed direction
Candidates who primarily identify as administrative assistants without execution ownership experience are unlikely to succeed in this role.
Tools
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Executive reporting systems
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Project management platforms
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Documentation systems
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Workflow and process documentation tools
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Calendar management systems
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Email management systems
What We Actually Care About
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You create structure when none exists.
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You notice ownership gaps before they become execution failures.
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You follow through on commitments without being reminded.
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You can tell a CEO "we are not ready to launch this yet" and support that recommendation with evidence.
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You turn ambiguous direction into clear actions for others.
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You help leaders move faster by reducing confusion, not by creating additional process.
What This Role Is NOT
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A calendar-only Executive Assistant role
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A task-taker position that waits for instructions
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A meeting scheduler with no responsibility for outcomes
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A role for candidates who avoid difficult accountability conversations
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A support position where success is measured by responsiveness instead of execution
Position Details
Type: Independent Contractor
Work Environment:
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Fully remote
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Fast-moving founder environment
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High-accountability culture
Hours:
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US-aligned business hours
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Availability during core executive operating hours required
Async Expectations:
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Operate independently
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Maintain clear written communication
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Document decisions and status updates proactively
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Drive progress without requiring constant check-ins
Benefits
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PTO
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HMO
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Fully Remote Work
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Competitive Salary Package
