Executive Creative Director

Headway Search Group; Toronto; Hybrid; CAD 140,000 - 210,000; Full time

Job summary

Headway Search Group is seeking an Executive Creative Director to lead and elevate our experiential marketing efforts. You will build and guide a high-performing creative team, translate objectives into compelling concepts, and drive clarity from concept to execution across multiple channels.

The role emphasizes strong people leadership, client-facing presentation prowess, and the ability to balance scope, timing, and margins in a fast-moving hybrid environment with travel for site visits and

Qualifications

• Senior creative leadership experience in experiential marketing, corporate events or related agency/client-side environments.
• Direct people management experience with a track record of setting expectations and developing talent.
• Experience leading senior client presentations and helping decision-makers buy into a creative direction.

Responsibilities

• Build and lead internal creative teams with clear expectations, accountabilities and decision rights.
• Coach and develop team members; provide candid feedback and address performance when required.
• Set the creative direction from brief to pitch, development, production and on-site execution.

Skills

Senior leadership

People management

Client presentations

Creative direction

Strategic decision making

Job description

What success will look like

Success in this role will be measured by the strength of the creative work, the effectiveness of the team and the organization’s ability to move from concept to execution with greater clarity and consistency.

You will be expected to:

• Build and lead a high-performing creative team with clear expectations, accountabilities and decision rights.
• Coach and develop team members, provide candid feedback, recognize strong performance and address performance issues when required.
• Set the creative direction from the initial brief through pitch, development, production and on-site execution.
• Improve how creative work moves through the organization by creating clearer briefs, stronger reviews, better handoffs and earlier decisions.
• Strengthen the quality of client pitches and presentations by translating business objectives into creative concepts that are compelling, practical and easy to understand.
• Develop the judgement and confidence of the team so that ownership can be delegated without compromising the quality of the final result.
• Ensure creative decisions reflect client objectives, production realities, budgets, timelines, scope and margin.
• Work across creative, production, sales and external partners to align teams around a clear direction.
• Help develop new event and incentive concepts that can be brought to market and adapted to different client needs.

Leadership and team management

People leadership is central to this role. You will:

• lead and manage internal creative teams and their respective leaders.
• establish priorities, set expectations, hold regular one-to-one meetings, coach different working styles and provide the feedback people need to improve.
• need to make difficult calls when required, including addressing performance or behaviour concerns promptly and fairly.

The goal is not to become the person who makes every creative decision. It is to build a team with the clarity, capability and accountability to make strong decisions and deliver consistently high-quality work.

Client and commercial leadership

The Executive Creative Director will play an important role with clients, particularly during pitches, presentations and critical decision points. You will:

• Help senior clients see and understand the experience being proposed, communicate the creative rationale clearly and explain feasibility, trade-offs and risk without over-promising.
• Bring commercial judgement to the work. Creative decisions need to support the client objective while respecting scope, timing, budget and margin.

What you will bring

You will have senior creative leadership experience in experiential marketing, corporate events, incentive programs, event production or a closely related agency or client-side environment.

Direct people management experience is essential. You have managed employees, not only freelancers, agencies or vendors, and can demonstrate your ability to set expectations, develop talent, handle difficult conversations and hold people accountable while maintaining trust.

You will also bring:

• Strong judgement in translating a business brief into a live experience that can be produced successfully.
• Experience leading senior client presentations and helping decision-makers understand and buy into a creative direction.
• A practical understanding of how creative decisions affect scope, margin, timing and client trust.
• The ability to communicate direction and trade-offs clearly with clients, senior leaders, employees and external partners.
• Enough hands‑on creative credibility to strengthen a treatment, pitch deck, script or show concept when needed.
• The judgement to know when to step into the work and when to let the team own the solution.
• The ability to build and manage a strong network of freelancers, creative professionals and specialist partners.
• Comfort working in a fast-moving hybrid environment and travelling for site visits, client meetings and program execution.

Who this role will not suit

This role is unlikely to suit someone who wants to remain primarily an individual creative contributor and views people management as secondary to the work.

It will also be challenging for someone who needs to approve every detail, finds it difficult to delegate meaningful ownership, prefers to remain at the concept stage or is uncomfortable making firm choices when budget, timing or production realities require trade-offs.

The organization operates with a combination of internal creative capability and external partners, so success also requires the ability to build and lead a flexible creative ecosystem rather than relying on a large internal department.