Executive/ Personal Assistant

Job Title: Executive/Personal Assistant

Reports To: Founder/CEO, Pretty River Group

Collaborates With: Athlete Institute Operations, Pretty River Group Operations

Location: Southern Ontario (Hybrid/Flexible, based out of Head Office) with regular travel as needed

Employment Type: Full-time, Permanent, Salaried

Salary: $50,000-60,000 per year

Position Summary

Pretty River Group is seeking a highly organized and detail-oriented Executive Assistant to provide comprehensive administrative and operational support to the CEO. This role manages scheduling, correspondence, travel coordination, and cross-entity liaison work to ensure the CEO's time is used effectively across a fast-paced, multi-entity organization. The position also includes personal assistant duties as required. The successful candidate will bring sound judgment, strong follow-through, and a high degree of discretion in handling confidential information.

Key Responsibilities

• Manage a complex, frequently shifting calendar across the organization's portfolio and affiliated entities, prioritizing the CEO's time against strategic priorities
• Screen and manage correspondence (email, calls, and messages) on the CEO's behalf, drafting responses, flagging priority items, and following up on outstanding items
• Prepare materials for leadership meetings, client meetings, and vendor or trade meetings, including agendas, briefing notes, and reports
• Coordinate complex domestic and occasional international travel itineraries, adapting quickly to schedule changes
• Liaise between the CEO and internal departments (Property Management, Facilities, Finance, Operations) and external stakeholders (clients, vendors, trades, partners)
• Track action items and commitments arising from meetings, and follow up to ensure timely completion
• Coordinate logistics for site visits, leadership meetings, and property walk-throughs involving the CEO
• Support special projects and cross-entity initiatives as assigned
• Provide personal assistant support to the CEO as required, including personal scheduling, travel coordination, reservations, and errands, applying the same discretion used in all executive duties
• Maintain strict confidentiality when handling sensitive organizational and personal information

Qualifications

• 3-5+ years of experience as an Executive Assistant, Personal Assistant, or similar role supporting senior leadership or C-suite executives
• Post-secondary education in business administration or a related field, or equivalent professional experience
• Exceptional written and verbal communication skills
• Proven ability to manage competing priorities in a fast-paced, multi-entity environment
• High degree of discretion and demonstrated ability to handle confidential information
• Strong proficiency with Microsoft Office / Google Workspace and calendar and travel management tools
• Comfortable using AI tools (e.g., Claude) to support drafting, research, and day-to-day productivity
• Valid Ontario Driver's License, preferred, for occasional local travel or errands
• Highly organized, proactive, and resourceful, with strong attention to detail and follow-through
• Comfortable working independently with minimal supervision and sound judgment under pressure
• Willingness to be occasionally available outside standard hours for events or urgent scheduling needs

Pretty River Group is an equal opportunity employer. We are committed to creating an inclusive and accessible recruitment process. Accommodations are available upon request for candidates participating in all aspects of the selection process. To request an accommodation, please contact [email protected]

This posting reflects a contract position for a new role. Pretty River Group accepts applications for this specific position on a rolling basis until filled.

Rusty Rock may use artificial intelligence tools to assist in the initial review of applications. All hiring decisions are made by our recruitment team.