Sr Manager, People

About Us

At Wynford, we create transformative live and digital experiences that strengthen cultures and drive results for Fortune 100 and emerging clients. From global incentive travel and large events to experiential workshops and product launches, we deliver best-in-class events rooted in empathy, collaboration, and relentless innovation. Our passion lies in valuing every voice, fostering ownership, and designing with the end-user at heart. 

About the Role

As the Senior Manager, People & Culture Strategy, you'll partner with the Senior Leadership Team to drive alignment, accountability, and engagement across Wynford's people initiatives. This role bridges strategy and execution—turning ideas into systems that strengthen culture, optimize operations, and advance our 2026 goals.

You'll lead a high-performing People & Culture team of two, overseeing payroll, benefits, internal events, and engagement. Together, you'll balance day-to-day excellence with long-term impact, while collaborating with external advisors and vendors to bring best-in-class practices to Wynford.

Working closely with eight SLT members, you'll bring clarity to complexity, influence without authority, and ensure our people strategy drives measurable results.

Work Arrangement

This is a fractional role requiring a commitment of 20–25 hours per week. Wynford's hybrid model requires in-office presence on Wednesdays and at least one other day per week, with flexibility for remote work outside of those times.

Key Responsibilities

• Design and drive strategic People & Culture initiatives
   that align with Wynford's 2026 goals, balancing day-to-day excellence with long-term impact.
• Guide and influence the Senior Leadership Team
   in setting priorities, translating ideas into actionable plans, and anticipating the organization's future people and culture needs.
• Lead and mentor a People & Culture team of two
  , overseeing payroll, benefits, internal events, and engagement initiatives while fostering professional growth and accountability.
• Bring structure and governance
   to HR and culture projects—turning complexity into clarity and ensuring consistent, high-quality execution.
• Shape requirements
   for the digitization of HR processes in collaboration with IT, leveraging your experience in tech-enabled HR solutions.
• Strengthen in-office culture
   through initiatives that build connection, accountability, and belonging.
• Standardize and support core People & Culture processes
  , including SOPs, onboarding, and internal communication frameworks.
• Collaborate with external advisors and vendors
   to bring best-in-class practices, tools, and insights to the organization.
• Develop and manage metrics
   to measure engagement, learning, and cultural impact, providing data-driven insights to leadership.
• Champion continuous improvement and operational excellence
   across People & Culture initiatives and practices.

What You Bring

• Bachelor's degree in Human Resources, Business, Organizational Development, or a related field (Master's or coaching certification an asset).
• Minimum 10 years of progressive experience in HR, Organizational Development, or People & Culture strategy.
• Strong background in Canadian employment law and compliance.
• Proven success managing cross-functional initiatives and influencing senior executives.
• Track record of designing scalable frameworks and leading change within fast-paced, creative organizations.
• Exceptional facilitation, communication, and stakeholder management skills.
• Strategic systems thinker with strong operational discipline.
• Comfortable navigating ambiguity and prioritizing competing needs.
• Advanced knowledge of culture-building, engagement design, and change management.

Who You Are

• A 
  coach and mentor

who builds confidence, strengthens capability, and gives consistent, actionable feedback to help others grow.
- A 
calm, clear communicator

who leads through ambiguity with composure, transparency, and resilience.
- A 
champion of accountability

who sets clear expectations, follows through, and builds a culture of ownership and results.
- An 
operations-minded leader

who drives excellence through smart systems, process improvement, and consistent, high-quality execution.
- A 
strategic connector

who aligns daily work with big-picture goals and co-creates practices that elevate team performance.
- A 
rust-based delegator

who assigns responsibility with clarity, encourages autonomy, and avoids micromanagement.
- A 
culture builder

who fosters psychological safety, shared norms, and open, constructive communication.
- A 
training developer

who collaborates with senior leaders to create effective onboarding and development programs with measurable impact.

What We Offer at Wynford:

Total Compensation:

Competitive salary with a comprehensive benefits package. 

Dog-Friendly Office:

Bring your furry friend to work for good vibes. 

Time Off:

Enjoy paid time off, including a winter holiday closure, birthday off, and additional personal time. 

Professional Development:

Access monthly training, industry memberships, and learning opportunities. 

Wellness:

Benefit from health & dental plans, fitness discounts, and an annual stipend for your wellness needs. 

Bonuses & Incentives:

Participate in a company-wide bonus structure and recognition programs like the DarWyn Awards. 

Work-Life Balance:

We believe in the power of being in the room. Our hybrid model requires two in-office days per week, with Wednesdays as our anchor day. For leaders, presence matters—in on Wednesdays and at least one other day to model mentorship and culture. Outside of that, enjoy the flexibility to work where you work best.
  

Travel & Exploration:

Opportunities to attend global FAM trips, tradeshows, and supplier events to fuel creativity and industry connections. 

Extra Perks:

Enjoy discounts on activities, retail stores, team lunches, fun off-site gatherings, and a culture that celebrates curiosity and collaboration. 

Send Us Your Resume

Interested applicants should send their resume and cover letter to 

.  
In your cover letter please tell us why this opportunity is interesting to you.

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.