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 recent 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
As Senior Director, Client Leadership, you will provide executive leadership for Candybox's most important client partnerships while helping shape the strategic direction of the Client Leadership function.

You will remain actively involved in major client initiatives, but your impact will extend beyond individual accounts. You will help drive enterprise client growth, agency expansion, financial performance, new business and the continued evolution of how Candybox leads and serves its clients.

Agency Client Strategy

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.

Help evolve Candybox's Client Leadership model as the agency grows.

Serve as executive sponsor for Candybox's largest and most strategic clients.

Build deep, trusted relationships with C-suite and senior client stakeholders.

Lead executive strategy sessions, Quarterly Business Reviews and annual planning conversations.

Guide Client Leadership teams through complex client, business and relationship challenges.





Ensure Candybox is consistently positioned as a valuable strategic partner to senior client stakeholders.

Strengthen long-term client partnerships and create mutual business value.

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.

Strategic Campaign Leadership

Participate directly in the development of major client and campaign strategies.

Guide teams in solving complex marketing and business challenges.

Ensure integrated campaigns remain aligned with client business objectives and Candybox standards.

Challenge thinking and help teams strengthen the effectiveness and business impact of their recommendations.

Remain close enough to priority accounts to ensure strong strategy translates into exceptional execution.

New Business & Agency Growth

Lead high-value new business opportunities and strategic partnerships.

Shape proposal strategy, executive presentations and agency positioning for major opportunities.

Lead or participate in senior-level pitches and business development conversations.

Identify opportunities to expand Candybox services based on evolving client and market needs.

Develop strategic partnerships that strengthen Candybox's market position.

Use enterprise relationships and market insight to help drive broader agency growth.

Partner closely with the COO and Executive Leadership on agency strategy.

Contribute to service innovation, operational planning and future growth initiatives.

Ensure Client Leadership priorities align with Candybox's overall business strategy.

Bring client and market insight into senior agency decision-making.

Represent Candybox externally through senior client relationships, strategic partnerships and appropriate industry opportunities.

Help shape how Candybox positions itself within the market and creates long-term value for clients.

Oversee financial performance across strategic client portfolios.

Drive sustainable revenue growth and long-term account value.

Guide Client Leadership teams on pricing, scope and profitability.

Monitor portfolio performance and identify commercial opportunities or risks.

Balance strategic ambition and campaign excellence with financial sustainability.

Partner with Executive Leadership on resource, investment and portfolio decisions.

Set the vision,



priorities and performance expectations for the Client Leadership team.

Build a high-performing, accountable and collaborative team culture.

Coach and develop Client Leadership professionals through regular feedback, development planning and performance conversations.

Strengthen the strategic, commercial and leadership capabilities of the team.

Address performance challenges promptly and consistently.

Develop future leaders and create stronger capability across the Client Leadership function.

Model Candybox's values, Success Habits and leadership expectations.

Skills

Executive-level strategic thinking and business judgment

Exceptional client relationship and stakeholder-management capability

Solid 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

Ability to influence, challenge and build alignment at senior levels

Advanced presentation, communication and negotiation skills

Proven ability to identify and develop enterprise growth opportunities

Strong new business and pitch leadership capability

Ability to lead complex multidisciplinary teams

Strong coaching, mentoring and leadership-development skills

Ability to balance long-term strategic thinking with active involvement in critical client initiatives

Sound judgment in complex, ambiguous or high-pressure situations

Ability to navigate change and lead effectively in a fast-moving agency setting

Proficient in Apple and Google Workspace environments

Ability to quickly learn reporting, project-management and technology platforms

Qualifications

10+ years of progressive marketing or advertising experience , including significant agency experience

Demonstrated experience leading large, complex and enterprise-level client relationships

Extensive experience working directly with senior executives and C-suite stakeholders

Proven track record of growing significant client accounts and long-term client value

Demonstrated experience leading major current business opportunities and strategic pitches

Experience overseeing account revenue, pricing, budgets, scopes and profitability

Experience providing strategic leadership across integrated marketing disciplines

Proven experience leading and developing senior client-service or Client Leadership professionals

Strong understanding of integrated marketing across digital and traditional channels

Experience contributing to agency or business-level strategy

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

Work with an award-winning team that values innovation, collaboration and performance

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📌 Senior Director, Client Leadership (Ontario)
🏢 Rippling
📍 Ontario