Guest Experience Manager - Checkmate

About the role

The Guest Experience Manager is responsible for delivering a highly personalized, VIP-caliber guest journey at CheckMate Artisanal Winery. This role operates with an owner's mindset in a lean, entrepreneurial structure, leading the overall success of the winery guest experience business.

Responsibilities

• 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
• 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

Requirements

• 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
• Ability and willingness to travel heavily in market and represent the winery during events, member experiences, sales opportunities, and other high-value brand moments

Qualifications

• Comfortable collaborating cross-functionally with brand, marketing, fulfillment, winemaking, engineering, and operational partners to deliver shared winery objectives

Skills

• Exceptional interpersonal and customer service skills
• Strong organizational and project management skills
• Ability to work independently and as part of a team
• Proficiency in Microsoft Office Suite

Benefits

• 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
• Flexible paid time off
• Extensive learning and development programs

Pay

$80,000 - $90,000 annually

Schedule

Full-time position