Executive Assistant to CEO

About Oxford Road

Oxford Road is the world’s premier independent audio ad agency. We make ads people actually want to listen to in order to grow companies we truly believe in. If you’re curious, have a deep love of audio, and want to help make the ads work in a high-trust, supportive culture, we want to talk to you.

About the role

The Executive Assistant to the CEO exists for one purpose: to maximize the CEO's time, efficiency, and daily execution. This role owns the calendar, logistics, and administrative infrastructure that keeps the CEO operating at full capacity. It requires someone who is exceptionally organized, exercises strong independent judgment, and communicates with clarity and precision in every direction.

This is not a role that operates by waiting to be told what to do. The EA anticipates needs, structures information before it is requested, and makes confident independent calls within defined scope. The CEO should never have to think about logistics, scheduling, or administrative execution. That thinking belongs to this role.

The EA works in close coordination with the Chief of Staff. The Chief of Staff shapes what should be on the CEO's calendar. The EA owns executing that calendar flawlessly. The two roles are distinct and must stay that way.

What you'll do

Calendar & Time Management

• Own the CEO's calendar end-to-end: schedule, protect, and sequence the CEO's time based on defined priorities
• Apply consistent gatekeeping: evaluate all scheduling requests, decline or reschedule conflicts, and protect high-value focus time without requiring the CEO to intervene
• Ensure all prep materials, briefing documents, and supporting information are organized and available before every commitment
• Coordinate with the Chief of Staff on calendar priorities, upcoming key meetings, and scheduling decisions that require strategic input

Meeting & Communication Support

• Schedule and coordinate all internal and external meetings, ensuring all parties have the information they need in advance
• Prepare or source agendas, materials, and pre-read documents for all CEO meetings
• Track follow-ups, action items, and reminders arising from CEO meetings and communications, ensuring nothing falls through
• Triage the CEO's inbox continuously, using AI-assisted tools to route every email to the correct owner: emails within EA scope are handled directly, emails requiring strategic input are escalated to the Chief of Staff, and all other emails receive a draft response in the CEO's voice for review or direct send
• Maintain response discipline across the CEO's inbox: emails tied to revenue, commercial relationships, or financial commitments are responded to or escalated within 24 hours; all other correspondence within 48 hours
• Draft non-strategic replies on behalf of the CEO, manually or AI-assisted, that are accurate in tone, clear in content, and indistinguishable in quality from communications the CEO would send personally

Logistics & Execution

• Plan and coordinate all CEO travel end-to-end: flights, accommodation, ground transportation, itineraries, and contingency planning
• Manage CEO expenses: track, organize, and submit expense reports accurately and within required timelines
• Coordinate internal and external events as needed, including logistics, communications, and on-the-day execution
• Anticipate logistical needs before they arise and resolve them without waiting to be asked

Personal & Professional Coordination

• Manage personal scheduling, errands, and coordination needs as defined by the CEO
• Coordinate across office and household needs as required, handling personal logistics with the same standard of execution as professional ones
• Maintain strict confidentiality across all personal and professional matters handled in this role

AI-Enabled Execution

• Actively apply AI tools to every aspect of the role: drafting communications, organizing information, preparing briefing materials, managing scheduling complexity, and identifying ways to increase the CEO's operational efficiency
• Stay current on emerging AI tools and bring forward applications that could improve the quality or speed of executive support
• This role is expected to be a practitioner, not a passive observer: AI fluency is a core competency, not a bonus

Operating Cadence

• Daily: Calendar review, logistics preparation, and proactive anticipation of CEO needs for the next 24 to 48 hours
• Weekly: Alignment sync with Chief of Staff on calendar priorities, upcoming meetings, prep requirements, and follow-ups
• Monthly: Expense reconciliation, travel review, and standing process check to identify any recurring friction or inefficiency

What Success Looks Like

• The CEO never thinks about logistics, scheduling conflicts, or missing prep materials: this role has handled it
• The calendar reflects the CEO's actual priorities, not whoever asked most recently
• Every meeting the CEO walks into has a clear agenda, the right materials, and no avoidable surprises
• Travel, expenses, and logistics are executed without error and without requiring the CEO's involvement in routine decisions
• Communications sent on behalf of the CEO are indistinguishable in quality from those the CEO would send personally
• The Chief of Staff and EA operate as a seamless pair: strategic direction and operational execution are always in sync
• AI tools are visibly embedded in how this role works, producing higher quality output faster than would otherwise be possible

Key Performance Indicators

Calendar & Preparation

• Meeting Prep Completion: 100% of CEO meetings have confirmed agendas and required materials in place at least 24 hours in advance
• Calendar Accuracy: zero scheduling conflicts, double-bookings, or missed commitments attributable to EA error
• Gatekeeping Effectiveness: CEO time is consistently allocated to defined priorities, with no reactive schedule creep from unfiltered requests

Logistics & Execution

• Travel Execution: 100% of travel itineraries confirmed and delivered error-free, with contingency plans in place for complex trips
• Expense Submission Timeliness: 100% of expense reports submitted within required timelines with zero material inaccuracies
• Logistics Error Rate: zero avoidable errors in scheduling, travel, or administrative execution on a rolling monthly basis

Communication & Responsiveness

• Response Timeliness: emails tied to revenue or commercial commitments responded to or escalated within 24 hours; all other correspondence within 48 hours, with zero items falling outside these windows without documented cause
• Email Triage Accuracy: all CEO inbox items correctly routed (EA-handled, Chief of Staff-escalated, or draft-prepared) with no misdirected or unactioned emails; draft quality requires zero substantive corrections before send

CEO & Chief of Staff Alignment

• Weekly EA and Chief of Staff sync completed without exception: calendar priorities, prep requirements, and follow-ups are aligned before the week begins
• CEO Operational Friction: qualitative and direct feedback from CEO on whether administrative and logistical friction is trending toward zero

Qualifications

Skills & Abilities

The strongest candidates will demonstrate:

• Exceptional organizational ability: the CEO's calendar, logistics, and administrative infrastructure are complex and fast-moving; this role requires someone for whom no detail gets lost
• Strong independent judgment and discernment: the EA makes confident, well-reasoned calls within defined scope without escalating decisions that are theirs to make
• Outstanding verbal and written communication skills: every email, message, and conversation reflects the same high standard; this role communicates on behalf of the CEO and that standard is non-negotiable
• High discretion and confidentiality: this role operates at the center of sensitive information and is expected to handle all of it with absolute professionalism
• Ability to work at pace without sacrificing accuracy: fast-moving environments are the norm, not the exception
• Active AI fluency: demonstrated current use of AI tools to produce better work faster, with genuine curiosity about what is possible and a track record of applying it
• Proactive anticipation: sees what is coming before it arrives and has already addressed it