South Okanagan Winery jobs

Flexible Transition Opportunity | Part-Time to Full-Time

We are seeking an exceptional Executive Assistant to serve as the trusted right hand to a highly active business CEO. This is far more than a traditional administrative role. It is a unique opportunity for an experienced professional who thrives in a dynamic environment supporting a diverse portfolio of business interests, investments, properties, hospitality ventures, and executive commitments.

The successful candidate will become a trusted partner to the CEO, providing seamless support across business operations, executive travel, events, confidential administrative matters, and office management. This individual must possess impeccable judgment, unwavering discretion, exceptional organizational skills, and the confidence to interact professionally with senior executives, business leaders, professional advisors, government officials, and other distinguished stakeholders.

This role requires someone who anticipates needs before they arise, solves problems independently, and consistently delivers a first-class experience for the CEO, guests, and business associates.

A Unique Transition Opportunity

This position represents a rare opportunity to work alongside and learn from the CEO’s long-standing Executive Assistant, who has been a trusted partner for more than 20 years and is beginning a planned transition toward semi-retirement.

Over the next 24 months, responsibilities will be thoughtfully and gradually transferred, allowing the successful candidate to gain a deep understanding of the CEO’s preferences, business relationships, and expectations while benefiting from hands-on mentorship and knowledge transfer.

To support this transition, the position may initially be structured on a flexible or part-time basis, with hours and responsibilities evolving over time based on the needs of the CEO and the successful candidate's progression into the role.

The nature of the position is dynamic, and workload requirements will ebb and flow depending on business activities, travel schedules, events, and project demands. As the transition progresses, the expectation is that the role will ultimately develop into a full-time position serving as the CEO’s primary Executive Assistant and trusted advisor.

Key Responsibilities

Executive Support

• Manage the CEO’s complex calendar, appointments, meetings, and commitments.
• Coordinate internal and external meetings, including agendas, briefing materials, presentations, meeting packages, and follow-up items.
• Arrange catering and hospitality services for executive meetings and office functions.
• Prepare correspondence, invitations, presentations, and executive documentation.
• Act as a key liaison between the CEO and senior business relationships.
• Maintain strict confidentiality in all matters relating to the CEO and associated business interests.

Executive Travel & Hospitality Coordination

Plan, coordinate, and execute complete travel experiences for the CEO and, where required, invited guests.

Responsibilities include:

• Coordinating all aspects of domestic and international travel, including commercial and private aviation, executive ground transportation, accommodations, hospitality services, and special requests.
• Creating detailed itineraries, travel packages, and guest information kits.
• Arranging event tickets, reservations, and unique experiences based on the CEO's preferences.
• Coordinating travel arrangements for accompanying guests when required.
• Managing travel changes, delays, and unforeseen issues in real time.
• Providing support outside regular business hours when travel or urgent matters require attention.
• Occasionally travelling with the CEO to provide on-site executive support.

Event & Guest Experience Management

• Coordinate executive dinners, receptions, private events, celebrations, and social gatherings.
• Design and distribute invitations and guest communications.
• Track RSVPs and provide attendance updates and reporting.
• Coordinate venues, vendors, catering, entertainment, transportation, and guest logistics.
• Create polished guest experiences that reflect the CEO's standards and expectations.

Confidential Administrative Support

• Manage confidential matters on behalf of the CEO with the utmost discretion and professionalism.
• Coordinate appointments, including legal, financial, and professional appointments.
• Pay and track personal invoices and related administrative expenses.
• Coordinate couriers, deliveries, and special requests.
• Research, source, and coordinate gifts, special occasions, and personal acknowledgements on behalf of the CEO.
• Assist with special projects and priority matters as directed by the CEO.

Office Management & Reception

• Serve as the first point of contact for visitors and incoming calls.
• Maintain a professional and welcoming office environment.
• Ensure executive offices, meeting spaces, kitchens, and common areas remain fully stocked, organized, and guest-ready.
• Coordinate office vendors and service providers, including maintenance, landscaping, cleaning, shredding, water delivery, office supplies, and other facility-related services.
• Process and track routine office invoices and operating expenses.
• Coordinate service calls and contractors when facility issues arise.
• Ensure the CEO's office is consistently stocked with supplies, refreshments, beverages, and hospitality items.
• Provide reception coverage and administrative support for a small professional office environment.

What We're Looking For

The ideal candidate is:

• Highly organized and exceptionally detail-oriented.
• Professional, polished, and confident interacting with senior executives and distinguished guests.
• Resourceful, proactive, and solutions-focused.
• Comfortable handling highly confidential and sensitive information.
• Able to anticipate needs and act with minimal direction.
• Creative and capable of producing visually appealing invitations, presentations, and event materials.
• Calm under pressure and able to adapt quickly to changing circumstances.
• Service-oriented with a commitment to excellence.
• Flexible and available to provide support outside traditional business hours when travel or urgent matters require attention.

Qualifications

• Minimum 5 years of experience supporting a senior executive, entrepreneur, family office, private office, or high-net-worth individual.
• Exceptional written and verbal communication skills.
• Advanced proficiency with Microsoft Office and modern business technology platforms.
• Experience coordinating complex domestic and international travel.
• Event planning, hospitality, concierge, or executive support experience is considered a strong asset.
• Valid driver's license and ability to travel occasionally.

Compensation

A competitive compensation package will be offered based on experience, qualifications, and the evolving nature of the role.

This is an exceptional opportunity for a highly capable professional seeking a long-term position supporting a dynamic business CEO while becoming an integral and trusted member of a close-knit professional team.

Pay: $52,798.81-$91,832.73 per year

Work Location: In person