DIRECTOR STRATEGY INSIGHTS & PLANNING

• Job ID: 64069
• Job Category: Customer Service
• Division & Section: Customer Experience, Business Transformation & Sustainment
• Work Location: Metro Hall, 55 John Street, Toronto, ON, M5V 3C6
• Job Type & Duration: Full-Time, Permanent 

• Salary Range: $165,310.00 - $222,843.00

• Shift Information: Monday to Friday, 35 hours per week
• Number of Positions Open: 1
• Posting Period: 30-Apr-2026 to 14-May-2026

The Customer Experience (CX) Division leads enterprise-wide initiatives to improve how residents and businesses interact with the City. Focused on enhancing service excellence, the Division supports cross-corporate collaboration, innovation, and accountability through data-driven insights, experience design, and customer-first strategies.

The Director, Strategy Insights & Planning drives CX digital transformation, using AI, data and best‑in‑class technology to modernize how customer experiences are designed and delivered. The Director develops CX digital strategy and multi‑year roadmaps and leads transformation initiatives that measurably improve experience quality and service performance.

Strategic Leadership, Planning and Digital Transformation

• Develops, designs and implements functional policies and programs that make major changes in overall business performance based on long‑term needs.
• Contributes to the continuous improvement of divisional performance through analysis and the development and implementation of sound management practices and procedures, provides program management staff with direction and guidance, processes and tools to increase efficiencies and improve effectiveness of the services provided by this section.
• Establishes and leads a unified view of CX strategy, standards, business cases, roadmaps and governance.
• Develops the Division’s overall CX strategy by staying on top of industry trends, understanding and providing insights on the City’s customers and their evolving requirements, and identifying and recommending areas for improvement based on frequent analysis of service data and benchmarking.
• Establishes and delivers multi‑year work plans and prioritizes initiatives while integrating Mayor/Council priorities and corporate strategic directions, to achieve the digital transformation objectives and outcomes.
• Identifies emerging issues, priorities and sensitive/confidential matters that could impact objectives, and develops strategies to address them.

Customer Experience Strategy, Design and Delivery

• Builds and plans channel centralization and oversees the development of the overarching CX and digital transformation strategy and standards to enable a seamless and cohesive CX at the City.
• Identifies emerging industry trends and develops ways to design an innovative and equitable experience for the public while understanding customer preferences.
• Provides innovative ideas for continuous improvement of the CX by understanding customer segmentation/personas/profiles and customer journeys.
• Plans projects and initiatives to deliver the City's CX vision while providing oversight, insight and frameworks to make strategic decisions.
• Establishes and measures adherence to corporate standards and identifies and recommends improvements to CX across all customer touchpoints.
• Develops, designs and implements the City’s CX policies in adherence to city‑wide standards, processes, technologies and services by promoting continuous improvement.
• Provides operational oversight, expert planning and leadership to establish a transparent digital transformation roadmap for the defined goals, objectives and customer‑centric benchmarks.

People Leadership

• Directs, through subordinate management staff, all activities of the section, delegating management responsibility.
• Leads and motivates a diverse workforce, ensures effective teamwork, ensures high standards of work quality and organizational performance, continuous learning and encourages innovation in others.
• Works collaboratively and in conjunction with the Corporate Employee Relations team when resolving employee relations issues. Provides guidance and advice regarding Corporate and Divisional policies and procedures and legislative requirements to all levels of staff and ensures consistent and timely implementation and adherence throughout the Division.

Stakeholder, Executive and Council Relations

• Engages with key leadership on strategic direction, transformation progress, performance data/trends, and operational challenges (e.g. Mayor’s Office, Council, Senior Leadership Team, and Corporate Leadership Team).
• Builds and maintains strong, collaborative relationships and partnerships with clients, senior leaders, external stakeholders, members of Council, Unions and Divisions to address and resolve conflicting demands and implement citywide solutions.
• Gathers political and/or executive support from various aspects of the organization, and negotiates with stakeholders (City Senior Leadership, Divisional Management, The Mayor’s Office, Councillors, etc.) with competing and conflicting goals/priorities, while maintaining positive working relationships.
• Represents the Division on various committees, task forces and teams.
• Prepares various reports for the Executive Director for consideration by Council and Standing Committees.
• Attends Committee and Council meetings and communicates with Executive and Senior Management.

Financial Management

• Develops, recommends and administers the annual budget for the section, and ensures that the section’s expenditures are controlled and maintained within approved budget limitations.

Key Qualifications

1. Post‑secondary education in Business Administration or an equivalent combination of education and extensive senior‑level experience.
2. Extensive strategic leadership experience in digital transformation, including AI‑enabled initiatives, within a large, complex organization.
3. Extensive senior management experience within digital transformation, leading multidisciplinary teams and managers.
4. Extensive experience overseeing User Acceptance Testing (UAT) and Customer Relationship Management (CRM) system configuration to ensure customer‑facing digital solutions meet requirements.
5. Strong strategic, analytical and problem‑solving skills, with the ability to interpret customer insights, service data, benchmarking and emerging trends to inform decision‑making and recommendations.
6. Ability to encourage innovation and promote collaboration and continuous improvement.
7. Ability to operate effectively within a complex political environment, including working with senior leadership, Council, and external stakeholders on sensitive and high‑profile matters.
8. Strong communication, influencing and negotiation skills, with the ability to prepare executive‑level reports and present to committees and senior management.  

Equity, Diversity and Inclusion

The City is an equal opportunity employer, dedicated to creating a workplace culture of inclusiveness that reflects the diverse residents that we serve. Learn more about the City’s commitment to employment equity.

Accommodation

The City of Toronto is committed to creating an accessible and inclusive organization. We are committed to providing barrier-free and accessible employment practices in compliance with the Accessibility for Ontarians with Disabilities Act (AODA). Should you require Code-protected accommodation through any stage of the recruitment process, please make them known when contacted and we will work with you to meet your needs. Disability-related accommodation during the application process is available upon request. Learn more about the City’s Hiring Policies and Accommodation Process.