Design Strategist DS

📍 Job Overview

Job Title: Design Strategist DS

Company: The Canada Life Assurance Company

Location: Toronto, ON; London, ON

Job Type: Permanent Full Time

Category: Digital Strategy & Design Operations

Date Posted: 2026-01-06T00:00:00

Experience Level: 3-5 years (with 1+ year in a lead strategy role)

Remote Status: Hybrid

🚀 Role Summary

• Drive strategic initiatives within the Digital Customer Experience team to enhance Canadians' financial, mental, and physical health.

• Lead discovery processes to deeply understand business and customer needs, defining clear objectives and desired outcomes for digital projects.

• Translate complex business problems and user challenges into a cohesive strategic vision, aligning diverse stakeholders and digital teams.

• Act as a critical liaison between business lines and digital teams, ensuring seamless communication from problem identification through to tactical implementation.

• Champion an outside-in, customer-first perspective across Canada Life's digital ecosystem, influencing product and service design.

📝 Enhancement Note: While the title is "Design Strategist," the responsibilities and required skills clearly indicate a role focused on the operationalization of strategy within a digital product development context. This role bridges the gap between business needs, user insights, and the execution of digital initiatives, making it highly relevant to operations professionals focused on Go-To-Market (GTM) strategy, product operations, and customer experience optimization. The emphasis on aligning stakeholders, defining objectives, and translating problems into actionable visions aligns with core GTM operations functions.

📈 Primary Responsibilities

• Lead comprehensive discovery initiatives to deeply understand business goals, customer challenges, market opportunities, and operational constraints impacting digital products and services.

• Facilitate workshops and discussions to align diverse stakeholders, including business partners, designers, researchers, and technical experts, around a shared understanding of problem spaces and clearly defined objectives.

• Develop and articulate compelling narratives and strategic concepts through storytelling and clear communication to build consensus and momentum for a unified digital vision.

• Collaborate closely with product owners, designers, subject matter experts, and other cross-functional partners to identify and prioritize initiatives that balance immediate business needs with long-term strategic commitments.

• Interpret qualitative and quantitative research findings to inform the creation of key design artifacts such as personas, journey maps, and jobs-to-be-done frameworks.

• Serve as a primary point of contact and communication conduit between business lines and digital development teams, ensuring consistent and clear information flow throughout the project lifecycle.

• Advocate for and embed an outside-in, customer-centric approach into the development and evolution of Canada Life's digital offerings.

• Function as an internal thought leader and change agent, promoting best practices and innovative approaches in design thinking, strategic planning, and product management.

📝 Enhancement Note: The responsibilities emphasize a strong strategic and analytical component, common in GTM operations roles that require understanding market dynamics, customer needs, and translating them into actionable plans. The focus on stakeholder alignment and communication is crucial for successful GTM strategy execution.

🎓 Skills & Qualifications

Education: While specific degrees are not listed, a strong foundation in business, design, human-computer interaction, or a related field is implied.

Experience:

• 3-5 years of experience working with digital experience teams, with a strong preference for experience in user research and user experience (UX) methodologies.

Required Skills:

• Superior communication skills, with a proven ability to synthesize complex information into compelling narratives and build rapport with diverse stakeholders.

• Demonstrated talent for providing honest and constructive feedback to foster continuous improvement.

• Ability to build strong relationships and foster collaboration within cross-functional teams.

• Strong background in translating business problems and user challenges into a clear strategic vision.

• Demonstrated ability to align cross-functional teams around a defined problem and strategic objectives.

• High capacity for big-picture, systems thinking, understanding interdependencies within complex digital and non-digital systems.

Preferred Skills:

• Experience with user research methodologies (qualitative and quantitative).

• Experience in user experience (UX) design principles and practices.

• Familiarity with product management frameworks and agile methodologies.

• Experience in the financial services or insurance industry.

📝 Enhancement Note: The required skills highlight a blend of strategic thinking, communication, and interpersonal abilities, essential for operations roles involving cross-functional leadership and strategic planning. The emphasis on translating business needs into actionable strategies is a core competency for GTM operations.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Demonstrations of strategic recommendation development and execution leadership.

• Case studies showcasing the ability to translate business problems and user challenges into clear strategic visions.

• Examples of how qualitative and quantitative research findings were interpreted and applied to inform design artifacts (e.g., personas, journey maps).

• Documentation or descriptions of successful stakeholder alignment and consensus-building processes.

Process Documentation:

• Documented examples of leading discovery work to understand goals, challenges, and opportunities for digital initiatives.

• Case studies illustrating the process of aligning diverse stakeholders around a problem space and defining clear objectives and outcomes.

• Examples of how compelling stories and ideas were articulated to build momentum for a cohesive digital vision.

• Evidence of collaboration with designers, product owners, and SMEs to prioritize initiatives.

📝 Enhancement Note: For a role like this, a portfolio is crucial. Candidates should prepare to showcase their strategic thinking, problem-solving process, and ability to influence outcomes. The focus should be on demonstrating how they drive clarity and alignment within complex environments, a key aspect of GTM operations.

💵 Compensation & Benefits

Salary Range: CAD $68,400 - $119,800 annually. This range represents base salary only.

Benefits:

• Comprehensive total rewards program (details to be discussed during the recruitment process).

• Opportunity to contribute to enhancing the financial, mental, and physical health of Canadians.

• Work within a dynamic Digital Customer Experience team.

• Potential for professional development and growth within a large, established financial institution.

• Inclusion in a diverse and inclusive workplace that champions career and well-being.

Working Hours: Permanent Full Time. While specific daily hours aren't detailed, a standard 40-hour work week is typical for full-time roles. The hybrid nature suggests flexibility in scheduling.

📝 Enhancement Note: The provided salary range is specific to Canada Life and aligns with industry benchmarks for a Design Strategist role with 3-5 years of experience in the Toronto/London, Ontario markets. The average base salary for a Design Strategist in Toronto can range from $70,000 to $120,000 CAD, depending on experience and company. The hybrid work arrangement is common for roles that require both focused individual work and collaborative team interaction.

🎯 Team & Company Context

🏢 Company Culture

Industry: Financial Services & Insurance. Canada Life is a leading provider of life insurance, health insurance, investment, and retirement savings solutions.

Company Size: Large enterprise (part of Power Financial Corporation group). This implies robust processes, significant resources, and a structured environment.

Founded: Canada Life was founded in 1847. This long history signifies stability, deep market understanding, and established trust among its customer base.

Team Structure:

• The role reports to the Director, Strategic Initiatives and Innovation, indicating a focus on forward-thinking projects and strategic development.

• The position is within the Digital Customer Experience team, suggesting close collaboration with UX/UI designers, researchers, product managers, and potentially digital marketing or analytics teams.

Methodology:

• Emphasis on understanding customer needs through qualitative and quantitative research to inform strategic direction.

• Focus on aligning diverse stakeholders through clear communication and storytelling to drive consensus on digital vision and objectives.

• Application of systems thinking to navigate and improve complex digital and non-digital ecosystems.

• Advocacy for a customer-first perspective in all digital initiatives.

Company Website: https://www.canadalife.com/

📝 Enhancement Note: Canada Life's long history and its position as a leading insurer suggest a culture that values stability, trust, and long-term strategic planning. For operations professionals, this means opportunities to implement and refine robust processes within a well-established framework, while the "Digital Customer Experience" team implies an openness to innovation and modern approaches.

📈 Career & Growth Analysis

Operations Career Level: This role sits at an intermediate to senior level within the digital strategy and operations domain. It requires leadership in discovery and strategic alignment, bridging business needs with digital execution. It's a foundational role for driving strategic change within digital product development.

Reporting Structure: The Design Strategist reports to the Director, Strategic Initiatives and Innovation, placing them within a leadership-focused group responsible for future-oriented projects. This offers visibility to senior leadership and exposure to strategic decision-making.

Operations Impact: The Design Strategist has a significant impact on Canada Life's operational effectiveness by ensuring that digital initiatives are strategically aligned with business goals and customer needs. By defining clear objectives and fostering stakeholder alignment, they directly influence the success and efficiency of digital product development and deployment, ultimately impacting customer satisfaction and operational efficiency.

Growth Opportunities:

• Specialization: Deepen expertise in specific areas of design strategy, user research, or product operations within the financial services sector.

• Leadership: Progress into roles with broader strategic oversight, such as Senior Design Strategist, Product Lead, or Manager of Strategic Initiatives.

• Cross-functional Mobility: Transition into Product Management, UX leadership, or other GTM operations roles within Canada Life.

• Skill Development: Opportunities to lead larger, more complex discovery initiatives and influence enterprise-wide digital strategy.

📝 Enhancement Note: This role provides a strong platform for operations professionals to hone their strategic planning, stakeholder management, and communication skills, which are transferable to various GTM leadership roles. The emphasis on innovation within a stable company offers a unique growth trajectory.

🌐 Work Environment

Office Type: Hybrid work environment. This suggests a blend of in-office collaboration and remote work flexibility.

Office Location(s): Toronto, Ontario, and London, Ontario. These are major urban centers in Ontario, offering access to talent and resources.

Workspace Context:

• The hybrid model necessitates strong digital collaboration tools and practices to maintain team cohesion and productivity.

• Expect a professional, corporate environment within one of Canada's largest financial institutions.

• Opportunities for collaboration with diverse teams, including designers, researchers, product owners, and business stakeholders, both in person and virtually.

• Access to modern digital tools and platforms to support strategy development, research analysis, and communication.

Work Schedule: Permanent Full Time. Standard business hours are anticipated, with the hybrid arrangement allowing for some flexibility in managing workdays, particularly regarding the balance between in-office and remote work.

📝 Enhancement Note: The hybrid nature of this role is typical for strategy and operations positions that require focused individual work for analysis and planning, alongside collaborative sessions for ideation and alignment. This environment supports efficient workflow for operations professionals.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: HR or recruiter screens for basic qualifications and cultural fit.

• Hiring Manager Interview: Discussion with the Director, Strategic Initiatives and Innovation, focusing on strategic thinking, experience, and problem-solving approach.

• Portfolio Review & Presentation: Candidates will likely be asked to present a case study or examples from their portfolio demonstrating their strategic approach, stakeholder alignment capabilities, and ability to translate complex problems into actionable visions.

• Team/Stakeholder Interviews: Interviews with cross-functional team members (designers, product owners, business partners) to assess collaboration style, communication effectiveness, and alignment with team dynamics.

• Final Interview: Potentially with a senior leader to discuss overall fit and strategic vision.

Portfolio Review Tips:

• Showcase Strategic Process: Clearly articulate your methodology for understanding problems, gathering insights, and developing strategic recommendations.

• Demonstrate Impact: Quantify results where possible. If not, clearly articulate the qualitative impact of your strategic contributions on project outcomes or business goals.

• Highlight Collaboration: Provide examples of how you effectively partnered with diverse stakeholders, managed differing perspectives, and built consensus.

• Tell a Story: Structure your portfolio presentations around compelling narratives that showcase your problem-solving journey and strategic decision-making.

• Customer-Centricity: Ensure your examples emphasize how you advocated for and incorporated the customer's perspective.

Challenge Preparation:

• Be prepared to discuss a hypothetical business challenge and outline your approach to discovery, strategy formulation, and stakeholder alignment.

• Practice articulating complex ideas concisely and persuasively, as if presenting to senior leadership.

• Consider how you would translate a user research finding into a strategic recommendation for a digital initiative within the financial services context.

📝 Enhancement Note: The emphasis on a portfolio review and presentation suggests that practical demonstration of strategic thinking and communication skills is paramount. Operations candidates should prepare to articulate their process and impact, mirroring the strategic planning and execution phases common in GTM roles.

🛠 Tools & Technology Stack

Primary Tools:

• Collaboration Platforms: Microsoft Teams, Slack, or similar for real-time communication and team coordination.

• Project Management Software: Tools like Jira, Asana, or Trello for tracking tasks and project progress.

• Documentation & Whiteboarding: Confluence, Miro, Mural for collaborative ideation, process mapping, and documentation.

Analytics & Reporting:

• While not explicitly stated, familiarity with data analysis tools (e.g., Excel, Tableau, Power BI) would be beneficial for interpreting research findings and communicating outcomes.

CRM & Automation:

• Experience with CRM systems (e.g., Salesforce) could be advantageous for understanding customer data context, though not a primary requirement.

• Familiarity with automation concepts, even if not directly using automation tools, is implied by the focus on efficiency and digital initiatives.

📝 Enhancement Note: While specific tools are not listed, a Design Strategist in a digital team will likely leverage collaboration tools, project management software, and digital whiteboarding platforms daily. Proficiency in these is expected for effective hybrid and cross-functional work. Familiarity with data interpretation tools is a strong plus.

👥 Team Culture & Values

Operations Values:

• Customer-Centricity: A core value, emphasizing the importance of understanding and serving customer needs in all digital initiatives.

• Collaboration: Strong emphasis on working effectively within cross-functional teams, building rapport, and fostering open communication.

• Innovation & Curiosity: Encouragement to explore new ideas, challenge the status quo, and continuously learn to improve digital experiences.

• Data-Driven Decision Making: Utilizing both qualitative and quantitative research findings to inform strategic recommendations and design choices.

• Impact & Accountability: Focus on driving tangible outcomes and taking ownership of strategic initiatives from discovery through to implementation.

Collaboration Style:

• Partnership-Oriented: Working closely with business lines, digital teams, and subject matter experts to co-create solutions.

• Facilitative: Guiding discussions, synthesizing diverse perspectives, and building consensus among stakeholders.

• Transparent Communication: Openly sharing research findings, strategic concepts, and feedback to ensure alignment and continuous improvement.

• Agile & Adaptive: Willingness to iterate on strategies based on new information and evolving circumstances.

📝 Enhancement Note: The company's stated values of diversity, inclusion, and well-being, combined with the emphasis on customer-centricity and innovation in the Digital Customer Experience team, suggest a supportive and forward-thinking work environment. Operations professionals who thrive on collaboration and data-informed strategy will find this appealing.

⚡ Challenges & Growth Opportunities

Challenges:

• Navigating a Large Organization: Balancing the need for agility and innovation with the structured processes of a large, established financial institution.

• Stakeholder Alignment: Effectively managing diverse stakeholder expectations and priorities across different business units.

• Translating Ambiguity: Converting complex, often ill-defined business problems into clear, actionable strategic roadmaps.

• Driving Change: Acting as a change agent to embed customer-centric strategies and new ways of working within existing organizational structures.

Learning & Development Opportunities:

• Strategic Frameworks: Gaining deeper expertise in various strategic planning and design thinking methodologies.

• Industry Insights: Developing a specialized understanding of the financial services and insurance industry landscape.

• Leadership Skills: Enhancing skills in stakeholder management, influencing, and leading strategic initiatives.

• Cross-functional Exposure: Working across multiple departments to broaden business acumen and operational understanding.

📝 Enhancement Note: The challenges presented are typical for strategy roles within large enterprises and offer significant opportunities for professional development in areas crucial for senior operations and GTM leadership.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex business problem you've faced and how you approached developing a strategic recommendation to solve it. What was the outcome?" (Focus on your process: discovery, analysis, stakeholder engagement, recommendation, execution).

• "How do you ensure alignment among diverse stakeholders with competing priorities when developing a new digital initiative?" (Highlight your communication, facilitation, and consensus-building techniques).

Company & Culture Questions:

• "What interests you about Canada Life and this specific role within our Digital Customer Experience team?" (Research Canada Life's mission, values, and recent digital initiatives. Connect your skills to their goals).

• "How do you approach advocating for a customer-first perspective, especially when it might conflict with immediate business pressures?" (Show your commitment to the customer and your ability to articulate the long-term value).

Portfolio Presentation Strategy:

• Structure: Organize your presentation logically, perhaps by project, focusing on the problem, your strategic approach, key decisions, challenges overcome, and the impact of your work.

• Data & Insights: Clearly present the qualitative and quantitative data that informed your strategy. Show how you synthesized information.

• Visuals: Use clear, concise visuals (diagrams, journey maps, etc.) to illustrate your points, but ensure the narrative is the focus.

• Conciseness: Be mindful of time. Practice to deliver your key messages effectively within the allotted period.

• Q&A Readiness: Anticipate questions about your decision-making process, challenges, and how you measured success.

📝 Enhancement Note: Interview preparation for this role should focus on demonstrating strategic thinking, problem-solving capabilities, and strong communication skills. Candidates should be ready to articulate their process and impact, drawing parallels to how GTM operations drive business outcomes.

📌 Application Steps

To apply for this Design Strategist position:

• Submit your application through the provided link on the Canada Life careers portal.

• Tailor your Resume: Highlight experience in digital strategy, stakeholder management, user research interpretation, and leading strategic initiatives. Use keywords from the job description such as "design strategy," "digital customer experience," "stakeholder alignment," and "strategic recommendations."

• Prepare Your Portfolio: Curate 2-3 of your strongest projects that demonstrate your ability to understand business problems, conduct discovery, develop strategic visions, and align teams. Be ready to present and discuss these in detail.

• Research Canada Life: Understand the company's mission, values, and recent digital endeavors. Prepare to articulate why you are a good fit for their culture and how you can contribute to their goals of improving Canadians' well-being.

• Practice Interview Responses: Prepare to answer behavioral and situational questions, focusing on your strategic process, collaboration skills, and adaptability. Practice articulating your portfolio examples clearly and concisely.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with The Canada Life Assurance Company before making application decisions.

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