Director, People and Culture

Headway Search Group; United States; Hybrid; CAD 103,320 - 117,096; Part time

Job summary

A company in the incentive events industry is seeking a HR leader for a fractional role of 20-25 hours per week with the potential of evolving into full-time. You will enhance workforce engagement, level up HR capabilities, and ensure proper integration of HR technologies. Strong candidates will have a background in managing HR functions, Canadian employment law knowledge, and the ability to navigate complex stakeholder environments. Compensation ranges from $75 to $85 per hour based on experience.

Qualifications

• Proven experience leading HR or People and Culture functions.
• Ability to build engagement foundations and measurable shifts.
• Familiarity with configuring HR technology for optimal use.

Responsibilities

• Measure workforce engagement and implement programming.
• Level up existing HR functions and enhance team capabilities.
• Ensure HR technologies are properly configured and integrated.

Skills

Leadership in HR or People and Culture

Experience in SMEs or founder-led organizations

Strong grounding in Canadian employment law

Emotional intelligence and stakeholder navigation

Education

Degree in HR, Business, or Organizational Development

Job description

Overview

Our client is an approximately 80-person company in the incentive events industry, a fast-moving, creative business that delivers high-impact live and digital experiences for some of the world's leading organizations. They have recently moved into a new space, have professional leadership in place, and have built a solid HR foundation to work from: a People and Culture team of two, established payroll and benefits processes, and core frameworks already in place.

This begins as a fractional engagement of 20–25 hours per week, with a genuine possibility of evolving into a full-time commitment for the right person. If you are looking for a fractional role that could become something more and you are the kind of leader who makes themselves indispensable this is worth your attention.

What Success Looks Like

In this role, you will be measured not by activity, but by impact. Within your first year, you will have:

• A more engaged, connected workforce. You have taken honest stock of the current engagement landscape, built on what is working, and introduced programming that deepens connection and commitment. Engagement is no longer something the organization hopes for, it is something it actively manages and measures.
• A people function that has levelled up. The existing HR team and processes are stronger, more consistent, and more capable. The team of two you lead has grown in confidence and skill. What was a solid foundation is now a high-functioning operation.
• HR technology that serves the people function. Working alongside the internal IT team, you have ensured that HR systems and productivity tools are properly configured and integrated not just adopted. The people function is getting what it needs from its technology, and the IT team has a clear, informed partner in you.
• Leadership that makes better people decisions. You have built genuine trust with the Senior Leadership Team and provided the grounded, candid guidance that helps them lead more effectively. Frameworks exist for the decisions that used to be made ad hoc and they are being used.
• A culture that is intentional, not accidental. Connection, accountability, and belonging are visible in how the organization operates day-to-day. The new space has become a home base that people actually want to be in.
• Stronger governance built on existing foundations. You have reviewed what is in place, filled the gaps, and ensured that SOPs, onboarding, and internal communication frameworks are current, understood, and consistently applied without overhauling things that are working well.

The Environment You'll Work In

This is a company with genuine heart, professional management, and real momentum. It also has owners who are deeply invested in the business and who remain actively involved sometimes in ways that require careful navigation. That is not a dysfunction to fix; it is a dynamic to manage. The right person will bring the emotional intelligence to work within that reality and the credibility to influence without always having formal authority.

You will not be walking into chaos. There is structure here, and a team that cares. What you will bring is the senior perspective to see what the next chapter of the people function needs to look like and the skill to lead the organization there.

What You Bring

Your background and track record demonstrate:

• Experience leading HR or People and Culture, including experience inheriting an existing function and taking it to the next level, ideally within growing SMEs or founder-led organizations.
• A history of building on existing engagement foundations to produce real, measurable shifts in how people feel and perform at work.
• The ability to assess what is working, strengthen what is not, and introduce the next layer of governance and practice without dismantling what came before.
• A working knowledge of HR technology that goes beyond the user level. You understand how systems and tools should be configured and integrated to support a high-functioning people operation, and you can work alongside an internal IT team to ensure they\'re built and maintained to serve that goal.
• Experience navigating complex stakeholder environments, including founders and owners who are deeply invested in the business.
• Strong grounding in Canadian employment law and HR compliance.
• A coaching instinct. You develop the people around you, give feedback that lands, and build capability rather than dependency.
• A degree in HR, Business, or Organizational Development is an asset.

Who You Are

You are calm under complexity and clear under pressure. You walk into an existing people function and quickly understand what is strong, what needs attention, and what needs to be left alone. You build trust with leadership, staff, and IT teams alike. You are outcomes-oriented without being transactional, and people-centred without being soft. You are someone who makes a fractional role feel full-time in its impact and who is open to that becoming the reality if the fit is right.

The Practicalities

Commitment: 20–25 hours per week (fractional), with the potential to evolve into a full-time role for the right person

Location: Hybrid — Wednesdays in-office (anchor day) + at least one additional day per week; remote flexibility otherwise

Compensation: $75–85/hr based on experience and fit; however we are open to discussion.