Senior Director, Client Leadership in Oakville

We are looking for an experienced, strategic and commercially minded Senior Director, Client Leadership to join our growing team! This is a senior agency leadership role for someone who knows how to build trusted relationships with executive clients, shape sophisticated marketing strategies, grow enterprise accounts and influence how an agency delivers value to its clients. The Senior Director, Client Leadership will provide executive leadership across Candybox's largest and most complex client partnerships while helping shape the future of our Client Leadership function and contributing directly to agency growth.

This role is a strong fit for someone who:

• Has significant agency leadership experience across large, complex and enterprise-level client relationships
• Is a trusted advisor to C-suite and senior executives and is confident leading high-level strategic conversations
• Can shape integrated marketing strategy around business outcomes, not simply campaign deliverables
• Has a strong commercial mindset and a proven ability to grow enterprise accounts, revenue and long-term client value
• Can lead major new business opportunities, strategic partnerships and high-value agency pitches
• Can influence across Strategy, Creative, Social Media, Performance Marketing, Technology and Project Management while developing a high-performing Client Leadership team

About Candybox: Candybox Marketing is an award-winning, full-service digital marketing agency with a studio in Oakville, ON. We specialize in CRO, SEO, PPC, Web Design + Development, Branding, Social Media, Marketing Automation and Multimedia. Listed on Canada's Fastest Growing Companies 7 years in a row. Certified as a Great Place to Work (2021-2025). We make the web sweet, and we want you on our team.

Key Responsibilities:

• Provide executive leadership for Candybox's most important client partnerships while helping shape the strategic direction of the Client Leadership function.
• Remain actively involved in major client initiatives, driving enterprise client growth, agency expansion, financial performance, new business and the continued evolution of how Candybox leads and serves its clients.
• Shape the long-term strategy for Candybox's client partnerships.
• Guide integrated marketing strategy across enterprise and strategically important accounts.
• Partner with Executive Leadership to align client strategy with Candybox's broader growth goals.
• Identify emerging client needs, marketing opportunities and potential service innovations.
• Provide strategic oversight across the agency's largest and most complex client programs.
• Build deep, trusted relationships with C-suite and senior client stakeholders.
• Lead executive strategy sessions, Quarterly Business Reviews and annual planning conversations.
• Ensure Candybox is consistently positioned as a valuable strategic partner to senior client stakeholders.
• Own enterprise-level account growth and strategic expansion across key client relationships.
• Identify opportunities to deepen partnerships, expand services and increase long-term account value.
• Influence agency positioning, pricing approaches and commercial strategy.
• Support the development of long-term agreements and high-value strategic partnerships.
• Ensure Client Leadership contributes meaningfully to overall agency revenue growth and profitability.
• Balance exceptional client outcomes with strong commercial discipline.
• Participate directly in the development of major client and campaign strategies.
• Guide teams in solving complex marketing and business challenges.
• Lead high-value new business opportunities and strategic partnerships.
• Shape proposal strategy, executive presentations and agency positioning for major opportunities.
• Develop strategic partnerships that strengthen Candybox's market position.
• Oversee financial performance across strategic client portfolios.
• Drive sustainable revenue growth and long-term account value.
• Set the vision, priorities and performance expectations for the Client Leadership team.
• Coach and develop Client Leadership professionals through regular feedback, development planning and performance conversations.
• Model Candybox's values, Success Habits and leadership expectations.

Skills:

• Executive-level strategic thinking and business judgment
• Exceptional client relationship and stakeholder-management capability
• Strong commercial and financial acumen
• Ability to connect marketing strategy to business growth, revenue and measurable outcomes
• Strong executive presence and confidence advising C-suite stakeholders
• Proven ability to identify and develop enterprise growth opportunities
• Strong coaching, mentoring and leadership-development skills

Qualifications:

• 10+ years of progressive marketing or advertising experience, including significant agency experience
• Demonstrated experience leading large, complex and enterprise-level client relationships
• Proven track record of growing significant client accounts and long-term client value
• Experience overseeing account revenue, pricing, budgets, scopes and profitability
• College Diploma, Bachelor’s degree or equivalent combination of education and relevant professional experience
• Some travel is required

Compensation:

• Base Salary: $125-$135K + Commission
• Career growth & professional development opportunities
• Full health benefits including dental, vision, massage, physio and more
• Group RRSP participation
• Birthday Day Off
• Hybrid work environment: 1-2 days/week in our Oakville studio