Fractional Executive Assistant to a Small, Purpose-Driven Gambling Harm Reduction Consultancy

Jay Robinson Consulting (JRC) Jay Robinson jay@jrobinson.ca +1 647 646 6965

Role Summary

The Executive Assistant (EA) to Jay Robinson is the operational cornerstone of a small, independent consulting practice focused on gambling harms prevention, regulation, and safer gambling strategy.

This is a high-trust, fractional role supporting a solo consultant working with regulators, operators, and industry leaders. There is no large team or layered structure. The EA works directly with Jay as a true right hand.

The role is flexible and fully virtual.

The EA ensures that time, communications, travel, client coordination, and core systems run smoothly, accurately, and proactively. This requires judgment, structured thinking, disciplined follow-through, and strong attention to detail.

You will anticipate next steps, read carefully, and execute with consistency and reliability in a reputation-sensitive environment.

Core Responsibilities

1. Executive Support and Communications

Track time-sensitive correspondence with clients, regulators, conference organizers, and financial institutions

Draft, format, proofread, and finalize documents

Maintain precise file naming, version control, and digital organization protocols

Keep contracts, SOWs, invoices, and key client documents organized and retrievable

2. Calendar and Global Travel Management

Manage complex scheduling across time zones

Coordinate and book international and domestic travel, often multi-leg and time-sensitive

Secure flights, hotels, ground transportation, and conference registrations

Prepare complete itineraries with all confirmations and documentation organized and accessible

Anticipate bottlenecks, logistical risks, and scheduling conflicts before they arise

3. Microsoft Office and Operational Project Management

Strong working proficiency in Microsoft Office (Word, PowerPoint, Excel, Outlook)

Format professional decks and documents to client-ready standard

Use Excel confidently to track invoices, payments, deadlines, and project status

Maintain structured task lists and follow-up systems

Send reminders, track outstanding items, and liaise with clients or vendors as needed

This role does not require accounting credentials. It requires strong project management discipline, organized financial tracking, and consistent follow-through.

4. Client and Financial Coordination

Serve as a professional point of contact with clients, regulators, vendors, and financial institutions

Communicate clearly, accurately, and in alignment with JRC’s professional standards

Track invoices, payment confirmations, and banking correspondence

Flag discrepancies or missing information early

Maintain organized documentation for accountant and regulatory purposes.

Performance Expectations

Reads emails and instructions thoroughly

Executes accurately on explicit and detailed instructions

Maintains awareness of prior correspondence and context

Proactively identifies risks, gaps, or missing information

Operates independently with reliability and discretion in a regulated environment

Precision, consistency, and confidentiality are essential.

Working Style and Fit

Comfortable working directly with a solo consultant in a fast-paced, high-accountability environment

Builds and maintains simple, effective systems to support a busy but focused consulting practice

Values purpose-driven work in gambling harm prevention and safer play

Very strong problem-identification and problem-solving skills

Calm, steady, and solutions-focused under pressure

Low ego, high reliability, flexibility

Required Experience

• 5+ years supporting senior executives, consultants, or professionals in regulated environments
• Demonstrated experience managing complex global travel and executive scheduling
• Advanced Microsoft Office proficiency
• Strong client-facing communication skills
• Structured task management and disciplined follow-through

Hours and Compensation

20 to 30 hours per month, variable

Flexibility required based on travel cycles, conference seasons, and client deadlines

Compensation CAD $50 per hour, equivalent to about $97,500 full-time annualized

What Success Looks Like in the First 90 Days

• Calendar is fully under control, with clear prioritization, clean scheduling, and no missed or conflicting commitments
• Travel is proactively managed end-to-end, with complete, accurate itineraries and no last-minute issues
• Inbox and key communications are organized, with priority items surfaced and responses moving efficiently
• File systems, document naming, and version control are consistent, reliable, and easy to navigate
• Invoices, payments, and key documents are tracked accurately, with no gaps or missed follow-ups
• Simple, effective systems are in place to track tasks, deadlines, and client commitments
• Jay is spending less time on coordination and follow-up, and more time on