About Us

Wynford is a brand experience company with a focus on creative & event production, experiential events and incentive travel focused on partnering with our clients to strengthen their cultures and drive results through the power of transformational live and digital events and experiences. These include customized incentive travel programs, conferences, experiential workshops, launch events, and all things in between.  We employ approximately 80+ full-time employees. Our Head Office is in Toronto, ON.  Visit us at www.wynfordtwg.com for more information.

We are proud to have received, for 8 years running, the Great Place to Work award.   At Wynford we are passionate about the work that we do, and the clients that we partner with. We believe in having fun and celebrating our successes as well as one another.  We believe our business success can be attributed to our people.  We have and foster a culture as it is important to speak up, share feedback, and challenge one another to create new ways of doing things.  We have a flexible and trusting environment where you can bring your best self to your role.

About the Opportunity

This is a permanent full-time position with the flexibility to work in a hybrid role. You will partner across the business to help create an environment for people at Wynford to do their best & most engaging work. Reporting to the Chief Operating Officer, you will have administrative, operational, and strategic responsibilities for the program development and execution of events and manage the dedicated operation teams – with the opportunity to engage in all aspects of operations ranging from our Air, Registration, and Event/Program management. You are confident, curious, and passionate about your work. You think like an entrepreneur, and enjoy leading and mentoring team members throughout their career journey.

You are a critical and strategic thinker, go-getter, have a can-do attitude towards success. You are a natural problem solver, who possesses maturity and sensitivity, are solution focused and comfortable working in a fast-paced environment that demands robust deliverables. You are comfortable and enjoy wearing both a strategic and operational hat.

What You Bring:

  • 7-10 years’ experience working in a management role with experience across a broad range of operational activities. Track record for translating strategic thinking into actionable plans and output.
  • Post-secondary education, in project management, hospitality or other related field.
  • Hands on experience with the development of global events and incentive travel, operationally partnering with sales.
  • Technologically savvy; adept at in a Google Workspace and Microsoft Windows environment. Working knowledge of systems and databases.
  • Solid Excel and demonstrated skills in database management and financial planning.
  • Strong project management and analytical capabilities to oversee a large functional team, multiple programs and troubleshoot through barriers for delivery.
  • Oversees events, registration, events/program management and air business flow models with an eye for optimization.
  • Client relationship management is an asset.

What You’ll Do:

  • Lead and manage event operation teams to ensure best in quality client service for our customers, by enhancing processes and operational procedures to deliver programs on time and within scope and budget.
  • Lead teams to successful performance by managing their performance and development, recruitment and succession planning for Air, Registration, and Conference services.
  • Collaborate with the sales team and other internal departments to ensure communication is clear and provide strategic insight to enhance operational delivery.
  • Revise and refine training, procedures and process flow to enhance the quality and professionalism of the Wynford brand and service model.
  • Oversight on on-site program operations, delivery of white-glove service, and solutioning barriers and resolving issues.
  • Guidance and consultation on costs, sales, and ability to increase profits – directly impacting repeat sales through quality and advocacy of programs.
  • Represent the operations team in client RFP responses, presentations and in client/partner escalation issues ensuring adherence to SOW, AFS and MSA of all team members.
  • Partnering with finance to ensure we are protected financially and have proper business terms in place in order to manage all deposits, payment schedules per project.
  • Review all budgets, forecasted hours vs. actual hours for team members, review and approve timesheets, expense reports and cost centre reports, forecast headcount quarterly and annually
  • Quality control operations documents: key dates, budgets, program reports, event specs, all program communications materials (print and e-communications), room lists, document formatting and final reconciliation reports.
  • Oversight of our on-site (Trip Directors and any employees) management support for program operations, as required
  • Responsible for leading and influencing cross-functional teams in support of business objectives and customer objectives. Ensures company alignment and enforces timelines on projects with assigned teams to ensure successful and timely execution
  • Ensure a superior customer experience through best-in-class event delivery
  • Utilize analytics to measure success of programs, make modifications/recommendations for future programs-based performance analysis
  • Communicate insights to key decision-makers to help shape the future of the business
  • Actively create an environment which pushes for outstanding performance (operational excellence), from both the internal teams and from partners. Hold all stakeholders accountable for results and ensure necessary analysis is undertaken to improve future initiatives/performance.
  • Create an environment that fosters creativity, innovation, and partnership. Articulate a “best in class” expectation every day


  • Strong business acumen, including problem solving and critical thinking abilities, and initiative to link operational workflows and business strategy.
  • Proactive and action-oriented, lead by example and roll up your sleeves to ensure solutions are successfully implemented.
  • Create an environment that feeds curiosity, challenge orthodoxies and fuel continual learning and unlearning.
  • Handle complex / sensitive situations with confidence, integrity, and diplomacy. Trusted, expert resource for leaders and a valued source of sound advice for employees.
  • Multitask, meet multiple deadlines and adapt to changing conditions.
  • Exceptional communication and interpersonal skills, change management, facilitation, coaching and conflict resolution.
  • Strong presentation skills to communicate effectively with diverse audiences.

 Personal Attributes:

  • Embrace collaborative leadership, self-awareness, humility, adaptability, and authenticity.
  • Pursue goals with enthusiasm and instill the same in others. Possess a “can do” attitude. Able to work independently and “roll up your sleeves” to make things happen.
  • Excellent listening skills and genuine interest in the concern of others.
  • Strong interpersonal skills and effectively communicate with teams across the entire organization.
  • Exceptional problem solving and analytical skills with demonstrated ability to turn findings into executable plans.
  • Strong project management skills
  • Respond positively to change and have a “how can I make this happen” attitude.
  • Constantly question “why” and the “way” things are done in a constructive manner and thrive on change that improves results.

Send Us Your Resume!

Interested applicants should send their resume and cover letter to jobs@wynfordtwg.comIn your cover letter please tell us why this opportunity is interesting to you.**Please indicate VP, Operation, Wynford in the subject line of your email.**

We wish to thank all applicants in advance for your interest. Only those candidates selected for an interview will be contacted. Wynford is an equal opportunity employer. We are committed to inclusive, barrier-free recruitment and selection processes, and work environment in accordance with the Accessibility for Ontarians with Disabilities Act (AODA). We will be happy to work with applicants requesting accommodation at any stage of the hiring process.

We value the diversity of the people we hire and serve. Diversity at this organization means fostering a workplace in which individual differences are recognized, appreciated, respected, and responded to in ways that fully develop and utilize each person’s talents and strengths.

To apply for this job email your details to jobs@wynfordtwg.com.