The Winery

Located in the heart of the South Okanagan, CheckMate Artisanal Winery is set in a place of breathtaking natural beauty. The result of millions of years of geological activity, the winery nestles against the rugged, rocky outcroppings of Mt. Kobau that give the region and vineyards its distinct character.

Every detail creates a setting that welcomes guests and embraces the view.

The Guest Experience Manager is the on-property leader accountable for delivering a highly personalized, VIP-caliber guest journey at CheckMate Artisanal Winery. Operating with an owner's mindset in a lean, entrepreneurial structure, this role leads the overall success of the winery guest experience business, including fiscal discipline, revenue performance, team readiness, facility presentation, and operational excellence. In close partnership with Brand, Fulfillment, Marketing, Winemaking, Engineering, and other stakeholders, this role elevates the CheckMate brand through polished storytelling, exceptional service execution, member engagement, in-market representation, and high-value sales and event opportunities.

What you'll do:

• Lead the design, execution, and continuous elevation of ultra-premium guest experiences that are curated, personal, memorable, and reflective of CheckMate's luxury positioning
• Own a VIP-level service model that anticipates guest needs, recognizes returning guests and members, and uses guest insight, preferences, purchase history, and lifetime value to personalize every interaction
• Set and uphold uncompromising service and presentation standards, including arrival experience, pacing, glassware, table setup, cleanliness, building readiness, and the overall condition of guest-facing and back-of-house spaces
• Coach, train, onboard, schedule, and develop seasonal and year-round team members to deliver confident storytelling, polished hospitality, product knowledge, service discipline, and continuous improvement
• Own revenue performance across DTC channels, including onsite visitation, private and VIP experiences, offsite events, outreach, club acquisition, member retention, elevated clienteling, conversion, average order value, and long-term guest value
• Manage the fiscal and operational health of the guest experience business, including labour, controllable expenses, inventory, wine depletion, packaging, collateral, service supplies, budget discipline, and decisions that support profitable growth
• Analyze guest feedback, service observations, and performance metrics to refine the guest journey, strengthen ratings and loyalty, improve repeat visitation, and identify opportunities for service recovery or operational improvement
• Partner closely with Brand, Fulfillment, Marketing, Winemaking, Engineering, and other stakeholders to align priorities, resolve barriers, support product availability, and ensure sales, events, storytelling, and operational standards are executed with excellence
• Represent the winery with professionalism and brand presence through heavy in-market travel, event planning, member engagement, sales opportunities, private experiences, and strategic relationship-building activities

What you have:

• Bachelor's Degree in Business, Hospitality, Wine, Tourism, or a related field is preferred
• 5+ years of experience in luxury hospitality, premium winery guest experience, fine dining, private client services, luxury retail, or a comparable high-touch service environment
• 2+ years of leadership experience with demonstrated ability to coach teams to consistent, polished, and elevated service execution
• Proven results in premium sales, guest conversion, member engagement, or relationship-based revenue growth
• Strong presence on the floor with the ability to model calm, confident, gracious hospitality during high-profile visits, peak service periods, and service recovery moments
• Excellent written and verbal communication skills, with the ability to tailor tone, storytelling, and recommendations to each guest
• High attention to detail and service discipline, with an eye for presentation, cleanliness, pacing, and the subtle cues that define luxury hospitality
• Collaborative, creative storyteller and problem-solver with an entrepreneurial spirit, innovative drive, and commitment to achieving exceptional business results
• Strong business acumen with the ability to manage fiscal priorities, make sound operational decisions, and act like an owner in a fast-paced, flat, and entrepreneurial environment
• Comfortable collaborating cross-functionally with brand, marketing, fulfillment, winemaking, engineering, and operational partners to deliver shared winery objectives
• Ability and willingness to travel heavily in market and represent the winery during events, member experiences, sales opportunities, and other high-value brand moments

Why Join Us?

Mark Anthony is committed to hiring, engaging, and growing qualified, talented, and motivated team members at every level of our organization. We offer competitive compensation that recognizes individual and company performance. The typical hiring range for this position is $80,000 - $90,000 annually complemented by a bonus plan; the base pay is determined by market location and job-related knowledge, skills, experience, and education.

As part of our Total Rewards program, we are also proud to offer:

• Company-matched RRSP contributions
• Extended health and dental benefits, and mental health plans with 24/7 access to a primary care physician via Lumino Health
• Maternity & Adoption Leave Top Up and Paid Secondary Caregiver Leave
• Paid time off
• An extensive offering of world leading learning and development programs to empower your career development - in-person and digital offerings with internationally renowned resources like Franklin Covey and Lumina.

We are growing a lasting legacy in the beverage alcohol industry, with people first. Apply now!