Lead Wine Ambassador
Job Type: Seasonal (May-October 2026)

CheckMate Artisanal Winery
Golden Mile Bench, Oliver, B.C.

Your next move…

With meticulous precision and an uncompromising commitment to excellence, CheckMate Artisanal Winery focuses on small lots of luxury Burgundian-style Chardonnay and Merlot. Some of the most high-scored wines in Canada – including seven perfect 100-point scores. The story of CheckMate is one of innovation, passion, risk, and determination.

Why CheckMate?

We’re on an amazing adventure. We’re going where others aren’t, and we’re growing like others can’t as a result. We’re also innovators and disruptors. This means we are in a position to offer our people unique experiences, training, opportunities, and support to grow their careers. We believe in giving our people a path to their future, cultivating career possibilities and perfecting the skills and knowledge they need to be at their best.

As our Lead Wine Ambassador, you will…

• Lead by example on the floor, supporting and motivating the ambassador team.
• Act as a liaison to the GE Manager, providing day-to-day guidance and stepping in to assist with leadership responsibilities when needed.
• Drive wine sales and wine club growth through effective guest engagement, relationship-building, and confident communication.
• Support Wine Club administration, including outreach, processing, and assisting members with their needs.
• Utilize winery systems including C7 and TOCK to manage reservations, guest flows, and sales.
• Maintain high standards of service, presentation, and professionalism across all touchpoints.
• Proactively anticipate needs, take initiative, and require little direction to manage tasks effectively.

What We’re Looking For:

• Minimum 2 year of experience in a hospitality or retail environment
• Must have Serving It Right certification, as well as be of legal age to serve alcohol in BC
• Must be flexible as the hours of work will fluctuate with business volume
• Working days, evenings and weekends required
• You thrive in ambiguity and are comfortable with change
• You listen, take feedback, respond quickly, and take initiative with a sense of urgency
• You are authentic, diplomatic, thoughtful, and always have the best intentions
• Serving experience considered an asset

What’s in it for you?!

• Starting wage is $23/hour determined by job-related knowledge, skills, experience and education + Gratuities
• Wine Club incentive program
• Discounts at our Iconic Wineries of British Columbia including Mission Hill Family Estate, CedarCreek Estate Winery, Road 13 Vineyards and CheckMate Artisanal Winery
• Mentorship from a passionate and enthusiastic leadership and winemaking team
• Ongoing on the job training and commitment to wine education.