About Wynford
At Wynford, we create live and digital experiences for Fortune 100 and emerging clients, from incentive travel and large-scale events to workshops and product launches.
Behind those experiences is a team of people who bring creativity, expertise and commitment to everything they do. Our People & Culture team helps create an environment where employees can do their best work, managers have the support they need and our people processes support the business as it grows.
About the Role
We're looking for an experienced, hands-on Senior People & Culture Generalist who brings strong HR knowledge, sound judgment and the confidence to work independently while supporting employees and leaders.
Reporting to the Director, People & Culture, you'll take ownership of core HR operations, advise managers on people matters and lead improvements to our HR processes and systems.
This is a role that combines operational responsibility with meaningful advisory work. One day you might be helping a manager navigate a challenging employee situation, and the next you could be leading recruitment, improving onboarding or implementing our HR information system.
Wynford is a creative, entrepreneurial environment where priorities can shift and not every situation comes with a clear process or precedent. We're looking for someone who can navigate ambiguity, make practical decisions, respectfully challenge thinking and recognize when to involve others.
You'll work directly with leadership, bring a thoughtful People & Culture perspective to business decisions and help shape how our culture shows up in everyday experiences.
Salary range: $78,000 – 88,000
What You’ll Be Responsible For
- HR Operations: Manage the employee lifecycle, including employment documentation, benefits, employee changes, payroll coordination, compliance, recordkeeping and offboarding. Ensure processes are accurate, consistent and completed on time.
- Recruitment & Onboarding: Lead full-cycle recruitment for assigned roles and oversee the onboarding experience from accepted offer through the first 90 days, working closely with managers and internal teams.
- HR Systems & Process Improvement: Lead the day-to-day implementation and rollout of Folks HRIS, including data, configuration, workflows, testing and adoption. Identify gaps and improve processes to reduce manual work and create greater consistency.
- Performance & Development: Manage the operational delivery of performance and development processes, including goal setting, quarterly conversations, year-end reviews and calibration, while supporting managers in having meaningful performance discussions.
- Employee Support & Experience: Serve as a trusted first point of contact for employees and managers, providing practical HR guidance and supporting engagement, recognition, learning, internal communications and culture initiatives.
What You'll Partner On
- Employee Relations: Independently assess and advise on employee matters, including performance concerns, attendance, accommodations and workplace issues. Recommend fair, practical solutions and partner with the Director on complex or higher-risk situations, including discipline and terminations.
- Manager & Leadership Support: Coach managers through people challenges, difficult conversations and decisions. Bring forward risks, recommendations and different perspectives, respectfully challenging thinking when appropriate.
- People & Culture Improvements: Work with the Director and other leaders to strengthen HR practices, improve the employee experience and translate business priorities into practical people initiatives.
What Success Looks Like
In the first 6 to 12 months, success would look like:
- Employees and managers see you as a trusted, knowledgeable and practical HR partner who can independently move work forward.
- Core HR operations, recruitment, onboarding and performance processes are running reliably, with clear ownership, accurate information and consistent follow-through.
- Folks HRIS is implemented for Wynford's agreed priorities, with reliable data, effective workflows and meaningful adoption.
- You've improved processes, reduced unnecessary manual work and created clear documentation that makes HR operations easier to manage.
- Managers are receiving confident, thoughtful guidance on people issues and are better equipped to handle employee challenges.
- You're identifying issues, recommending solutions and contributing improvements that strengthen the employee experience and support the business.
Essential Experience & Capabilities
- Typically 5+ years of progressive HR experience, including broad generalist responsibilities and direct experience advising managers on employee relations and performance matters.
- Strong working knowledge of Ontario employment legislation and the ability to apply it thoughtfully to real workplace situations.
- Hands-on experience across recruitment, onboarding, benefits, HR administration, performance management and employee support.
- Experience implementing, administering or significantly improving HR systems and processes.
- Sound judgment, discretion and the confidence to independently assess situations, make recommendations and navigate sensitive conversations.
- Strong communication, relationship-building and organizational skills, with the ability to influence leaders, manage competing priorities and follow through on commitments.
We value demonstrated capability over years of experience alone. We're interested in what you've accomplished, how you approach challenges and your ability to apply your knowledge in practical situations.
Trainable Skills (Nice to Have)
- Experience with Folks HR (HRIS).
- Experience with HR reporting, workflow design, process automation, or data migration.
- Experience coordinating payroll changes and benefit administration in a Canadian organization.
- Experience in a lean HR team or a fast-moving, project-based organization would also be valuable.
- Experience in events, incentive travel, experiential marketing, hospitality, or another fast-moving project-based service environment.
Education
Post-secondary education in Human Resources, Business Administration or a related field is an asset. Equivalent relevant experience will also be considered.
You'll Likely Enjoy This Role If...
- You enjoy being a true HR generalist and are just as comfortable managing the details as you are discussing people challenges with leaders.
- You have strong HR knowledge but understand that good HR isn't about applying every policy or process in exactly the same way. It's about understanding the situation, being fair and making sound decisions.
- You're comfortable working in the grey, asking questions and finding practical solutions when the answer isn't immediately obvious.
- You can confidently share your perspective with leaders, including respectfully challenging an approach when you believe there's a better way.
- You like creating structure, improving processes and making things easier for others.
- You're proactive, resourceful and don't need someone to tell you every next step.
- You care about the employee experience and understand that culture is shaped by everyday decisions, behaviours and interactions.
- You're comfortable working in an environment where priorities shift and there is always something new to figure out.
This Role May Not Be the Right Fit If...
- You're looking for a role focused primarily on HR strategy rather than hands-on execution.
- You prefer highly structured environments where processes and decision-making paths are already clearly established.
- You're uncomfortable having challenging conversations or offering a different perspective to managers and senior leaders.
- You prefer predictable work where priorities rarely change.
- You need detailed direction before taking action or moving work forward.
What We Offer
Total Compensation: Competitive salary with a comprehensive benefits package.
Hybrid Work Environment: Flexibility with a hybrid working structure to support work/life balance.
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 WynList Awards.
Extra Perks: Enjoy discounts on activities, retail stores, team lunches, and fun off-site gatherings to keep the team spirit high.
Interested?
Send your resume and cover letter to jobs@wynfordtwg.com.
In your cover letter, tell us what interests you about this opportunity and what kind of operating environment helps you do your best work.
At Wynford, we’re committed to creating an inclusive workplace where every voice is valued. We welcome applications from all qualified candidates and will provide accommodation throughout the recruitment process in accordance with the Accessibility for Ontarians with Disabilities Act (AODA).
