Over 40 years ago, we founded our family winery with an audacious dream – to redefine what’s possible for Canadian wine in the eyes of the world. With a deep commitment to the Okanagan region, and a relentless passion to produce wines that can stand alongside the best in the world, our wines are crafted with bold precision and an uncompromising respect for the diverse vineyards and micro-climates here.

Our culture is unapologetically fast paced, entrepreneurial, and results driven. Each team member is a storyteller and makes an impact on a family-owned business that is building a lasting legacy in the Canadian and International wine industry. Our people have relentless drive to always raise the bar, a genuine entrepreneurial spirit, a passion, and love for what we do, to all act like owners, and to constantly innovate. We act with a sense of urgency, do everything possible to always overdeliver for our customers, and treat each other with humility and authenticity.

We love what we do. We’re all in. It’s how we have accomplished great things. Like our amazing products and our brand, we want to tell you the exciting story of our winery, its growth, and our people. We’re on an amazing adventure and we want you to help write the next chapter with us. We are building a lasting legacy in the wine industry, and we’ve only just begun

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!

Mark Anthony Group is an equal opportunity employer. We encourage applications from individuals of all backgrounds who are eligible to work in Canada. We thank all candidates for their interest in MAG and we will reach out to those candidates that are under consideration. If you are contacted for an interview and require accommodation during the recruitment process, please contact your recruiter.

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At Mark Anthony, we exist to Unearth the Extraordinary:

Our Purpose is not just a statement; it is a call to action that binds us together and ignites our passion for making a difference. It is the driving force behind why we do what we do every single day, connecting our global organization across all business units, roles, and locations. We are:

Best in Our Craft

We set the standard with a pursuit of excellence that can be found in everything from our products and processes to our plants and people.

Ambitiously Curious

We stay curious, dreaming big and navigating the unknown with an enduring belief in better.

Made With Humility

We bring humility, authenticity, fun, and support to every collaboration and celebrate wins as a team.

Daringly Disruptive

We disrupt the status quo, moving fast to seize opportunities and acting scrappy to stay ahead of industry giants.

Mark Anthony Group

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Guest Experience Manager - Checkmate