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Join The Team

We are hiring an Events Booker and Coordinator

(Wedding Experience Preferred)

We're looking for someone who can own the event booking process from start to finish, with a sales-oriented mindset to maximize revenue and guest satisfaction. If you have a background in wedding coordination, that's a major plus—we value the ability to handle the unique demands of weddings alongside our other signature events. Bring your unique vision to align with our ownership's goals and help elevate Rolling Grape Vineyard to new heights.

This role will require availability on days & weekends with opportunities for performance-based incentives tied to event sales and bookings.

đź’˛ $26-$30/hr based on experience

âž• Discounts on wine & food!

âž• Seasonal, part-time to begin with a gradual transition into full-time in April.

 

KEY RESPONSIBILITIES

  • Drive event sales by handling inquiries, pitching customized packages, and closing bookings for weddings, harvest dinners, live music events, and private functions.
  • Create and manage all event bookings from initial contact through contract signing, including client communications, negotiations, and follow-ups to ensure high conversion rates.
  • Coordinate and book weekly live music performances on Thursdays and Sundays, sourcing talent and aligning with our brand's vibe.
  • Develop event concepts and timelines, collaborating with clients to tailor experiences that fit their vision and our venue capabilities.
  • Oversee logistics, scheduling, and setup for events, including floor plans, vendor coordination, and onsite support as needed.
  • Work closely with kitchen, service, marketing, and operations teams to deliver seamless events, emphasizing clear communication and team support.
  • Manage ticketing systems, reservation platforms, event capacities, and revenue tracking to optimize profitability.
  • Build and maintain strong relationships with vendors, entertainers, partners, and clients to foster repeat business and referrals.
  • Monitor event budgets, generate performance reports, and identify opportunities for upselling or cost efficiencies.
  • Provide hands-on support during select events, including setup, execution, and teardown, with a focus on creating memorable guest experiences.

SKILLS & QUALIFICATIONS

  • Minimum 2 years of experience in event booking, sales, or coordination within hospitality, restaurants, or wineries (food/wine industry experience is a strong asset).
  • Proven ability to manage multiple bookings simultaneously while driving sales and revenue growth.
  • Wedding coordination background or demonstrated ability preferred, with experience in planning, timelines, and vendor management for high-end events.
  • Smart Serve certification required (or willingness to obtain upon hire).
  • Exceptional interpersonal, sales, and organizational skills, with a keen eye for detail and a creative flair.
  • Comfortable working flexible hours, including evenings, weekends, and holidays—hospitality is a 24/7 commitment!
  • Physically able to be on your feet for extended periods, assist with event setup, and handle light lifting.
  • Proficiency in event management software, ticketing systems, and Microsoft Office; familiarity with CRM tools for sales tracking is a plus.
  • A positive, proactive attitude with the ability to thrive in a fast-paced, growing environment.

Please note that the winery shuts down for the month of January & February, with the exception of Valentine's Day weekend.

Click below to send us your resume and a cover letter. Please include "Events Booker and Coordinator Application" in your subject line.

resume@rollinggrape.com

We are hiring an Events Manager 

(Wedding Coordination Experience Preferred)

We're looking for someone who can take charge of event operations from setup to teardown, with a hands-on approach to deliver seamless experiences. If you have a background in wedding coordination, that's a major plus—we value expertise in managing the intricate details of weddings alongside our other signature events. Bring your leadership and problem-solving skills to collaborate with our team and help make Rolling Grape Vineyard a premier destination for memorable occasions.

This role will require availability on days & weekends.

đź’˛ $26-$30/hr based on experience

âž• Discounts on wine & food!

âž• Full-time position beginning in the Spring

 

KEY RESPONSIBILITIES

  • Lead the execution of events, including weddings, harvest dinners, live music nights, and private functions, ensuring all aspects run smoothly and on schedule.
  • Develop detailed event timelines, run-of-shows, and checklists, coordinating with clients, vendors, and internal teams to bring concepts to life.
  • Oversee onsite logistics, including setup, staging, audio-visual needs, decor, and teardown, while troubleshooting any issues in real-time.
  • Manage vendor relationships during events, such as caterers, florists, entertainers, and photographers, to ensure timely delivery and quality standards.
  • Direct event staff, including servers, bartenders, and support teams, providing clear instructions and fostering a collaborative atmosphere.
  • Handle day-of client interactions, addressing needs, managing expectations, and ensuring exceptional guest experiences from arrival to departure.
  • Monitor event budgets in real-time, track expenses, and generate post-event reports on performance, feedback, and areas for improvement.
  • Coordinate with kitchen, service, marketing, and operations teams to align on event details and resolve any operational challenges.
  • Provide hands-on support during events, including physical setup, crowd management, and emergency response as needed.
  • Foster repeat business by gathering client feedback, building relationships, and identifying opportunities for enhancements in future events.

 

SKILLS & QUALIFICATIONS

  • Minimum 2 years of experience in event management or execution within hospitality, restaurants, or wineries (food/wine industry experience is a strong asset).
  • Proven track record of successfully managing multiple events simultaneously, with a focus on operational efficiency and guest satisfaction.
  • Wedding coordination background or demonstrated ability preferred, with hands-on experience in day-of management, timelines, and high-stakes vendor oversight.
  • Smart Serve certification required (or willingness to obtain upon hire).
  • Strong leadership, organizational, and problem-solving skills, with excellent attention to detail and the ability to remain calm under pressure.
  • Comfortable working flexible hours, including evenings, weekends, and holidays—hospitality is a 24/7 commitment!
  • Physically able to be on your feet for extended periods, manage event setup/teardown, and handle moderate lifting.
  • Proficiency in event management software, scheduling tools, and Microsoft Office; experience with project management platforms is a plus.
  • A positive, adaptable attitude with the ability to excel in a dynamic, team-oriented environment.

 

Please note that the winery shuts down for the month of January & February, with the exception of Valentine's Day weekend.

Click below to send us your resume and a cover letter. Please include "Events Manager Application" in your subject line.

resume@rollinggrape.com

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Hours Of Operation

Friday 4:30 - 9:30 PM

Saturday 4:30 - 9:30 PM

Where To Find Us

ADDRESS

260 County Rd. 2 Bailieboro, ON K0L 1B0

PHONE

705-991-5876

About Rolling Grape

Our winery is located on the family farm and in the middle of our vineyard for you to enjoy our wines and vines! Just 20 minutes South of Peterborough.

Coming soon.

Want promotional deals? Early access to harvest dinners and more? Join our newsletter for the inside scoop today!

 

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