Senior Product Design Manager

📍 Job Overview

Job Title: Senior Product Design Manager Company: OpenTable Location: Hybrid - Toronto, Ontario, Canada Job Type: Full-time Category: Product Design Management / UX Leadership Date Posted: 2025-10-30 Experience Level: 5-10 Years Remote Status: Hybrid (2 days in-office per week)

🚀 Role Summary

• Lead and manage a global team of talented product designers focused on CRM, Guest Data, and Platform initiatives to establish and drive high-quality user experiences.
• Oversee the design vision and execution for all restaurant-facing platforms, including native apps and web experiences, ensuring consistency and impact.
• Act as an influential partner within the UX team, optimizing processes, fostering innovation, and ensuring the professional development of direct reports.
• Collaborate closely with cross-functional teams including Product Management, Engineering, Research, Data Science, Design Systems, and Brand Design to deliver exceptional value.
• Drive a data-informed design approach, leveraging user insights and analytics to inform decision-making and product strategy.

📝 Enhancement Note: This role is a critical leadership position within OpenTable's UX team, focusing on the business-to-business (B2B) aspects of their platform. The emphasis on CRM, Guest Data, and Platform Teams indicates a strategic focus on restaurant partner success and operational efficiency, requiring a deep understanding of B2B user needs and complex system design. The hybrid model in Toronto suggests a need for strong remote collaboration skills alongside in-person team engagement.

📈 Primary Responsibilities

• Manage, mentor, and grow a global team of product designers, fostering a high-performing and collaborative design culture.
• Define and evangelize the design vision for restaurant-facing products, ensuring alignment with business objectives and user needs.
• Oversee the end-to-end design process, from concept and research to detailed UI/UX design and handoff to engineering.
• Champion best practices in user experience and visual design, ensuring the delivery of delightful, effective, and impactful user interfaces.
• Drive innovation by exploring new design solutions and technologies that enhance the restaurant partner experience and OpenTable's platform capabilities.
• Collaborate closely with Product Management to define product roadmaps and prioritize design initiatives based on user value and business impact.
• Partner with Engineering to ensure the successful and high-fidelity implementation of designs, providing ongoing support and guidance.
• Leverage data analytics and user research to inform design decisions, measure the effectiveness of solutions, and identify areas for improvement.
• Build strong relationships and consensus with stakeholders across various disciplines, effectively balancing user, team, and business needs.
• Contribute to the continuous improvement of design processes, workflows, and ways of working within the UX team and broader product development organization.

📝 Enhancement Note: The core responsibilities highlight a blend of people management, strategic design leadership, and hands-on execution oversight. The focus on "optimizing our processes and improving ways of working together" suggests a strong emphasis on operational efficiency within the design function itself.

🎓 Skills & Qualifications

Education:

• Bachelor's or Master's degree in Design, Human-Computer Interaction, Computer Science, or a related field, or equivalent practical experience.

Experience:

• 5-10 years of progressive experience in product design, with a significant portion in leadership or management roles.
• Proven track record of successfully leading design teams and managing complex design projects from conception to launch.
• Experience in establishing, implementing, and maintaining impactful user experiences, both personally and through team efforts.
• Demonstrated success in growing designers and design managers, motivating them, and supporting their career development.

Required Skills:

• Deep expertise in native app and web experience design, with a masterful understanding of platform-specific nuances and best practices.
• Exceptional visual design skills, with a strong portfolio showcasing a keen eye for aesthetics and usability.
• Extensive experience in design for B2B environments or complex, ambiguous problem spaces.
• Proficient in data-driven decision-making, consistently utilizing data and user insights to inform design strategy and product direction.
• Highly skilled in stakeholder management, adept at building consensus and balancing diverse needs across multiple disciplines.
• Strong systems-thinking, analytical, problem-solving, and interpretation capabilities.
• Ability to create and evangelize a compelling vision, developing comprehensive plans for its realization through a team.
• Excellent storytelling, verbal, and written communication skills, including the ability to develop and deliver impactful presentations.
• Critical thinking and collaborative approach, valuing feedback and constructive debate.
• Continuous introspection and a commitment to self-improvement and team growth.

Preferred Skills:

• Experience in the restaurant industry or a demonstrated passion for food and dining.
• Experience working on dual-market products or with global user bases.
• Familiarity with design systems and their implementation across large organizations.

📝 Enhancement Note: The qualifications emphasize both individual design craft and managerial capabilities, with a strong leaning towards B2B and platform-level design. The "5-10 years" experience level suggests a need for seasoned professionals who can lead independently while also developing junior talent. The explicit mention of "B2B or ambiguous spaces" is a key differentiator for operations-minded candidates.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• A comprehensive portfolio demonstrating a strong command of product design principles, UX methodologies, and visual design execution across native apps and web platforms.
• Case studies showcasing leadership in designing for B2B or complex platforms, highlighting problem definition, user research, design solutions, and tangible outcomes.
• Examples of how data and user analytics were integrated into the design process to inform decisions and measure success.
• Evidence of leading design teams, mentoring designers, and fostering a collaborative and innovative design environment.
• Demonstrations of effective stakeholder management and cross-functional collaboration in bringing design visions to fruition.

Process Documentation:

• Ability to articulate and document design processes, workflows, and best practices for team adoption and continuous improvement.
• Experience in optimizing design team operations, including agile methodologies, design system utilization, and collaboration with engineering.
• Proficiency in defining metrics and establishing frameworks for evaluating design quality and product impact.

📝 Enhancement Note: For a role of this seniority and focus on B2B platforms, the portfolio should heavily emphasize strategic thinking, team leadership, and the ability to translate complex business needs into user-centric solutions. Candidates should be prepared to discuss their process for managing design teams and driving operational efficiency within the design function.

💵 Compensation & Benefits

Salary Range: $165,000 - $200,000 CAD per year

Benefits:

• Generous Paid Vacation
• Time Off For Your Birthday
• Work From (Almost) Anywhere For Up To 20 Days Per Year
• Company-Paid Therapy Sessions Through SpringHealth
• Company-Paid Subscription To Headspace
• Annual Company-Wide Week Off A Year (team fully recharges without backlog)
• Paid Parental Leave
• Paid Volunteer Time
• Development Dollars for career growth
• Leadership development programs
• Access to thousands of on-demand e-learnings
• Travel Discounts
• Employee Resource Groups
• Private Health and Dental Insurance
• Life and Disability Insurance
• The role is eligible for an annual bonus and equity grant.

Working Hours:

• Standard 40-hour work week. However, flexibility is expected to accommodate global team collaboration across multiple time zones, which may include occasional communication outside of regular business hours via calls, Slack, or email. OpenTable adheres to local laws and regulations regarding working hours.

📝 Enhancement Note: The salary range is competitive for a Senior Product Design Manager role in Toronto. The extensive benefits package, particularly the focus on mental health, well-being, and career development, aligns with a progressive employer brand. The note on flexible working hours acknowledges the realities of global team management and is crucial for operations professionals to understand.

🎯 Team & Company Context

🏢 Company Culture

Industry: Technology / Hospitality / Food & Beverage Company Size: OpenTable is part of Booking Holdings, Inc., a large, established global company. OpenTable itself operates with a significant employee base, indicating a structured yet dynamic environment. Founded: OpenTable was founded over 25 years ago, bringing a wealth of experience and a deep understanding of the restaurant industry.

Team Structure:

• The Design team is part of a larger UX organization, with this role leading a global team of product designers.
• This role will work closely with Product Management, Engineering, Research, Data Science, Design Systems, and Brand Design, indicating a highly collaborative, cross-functional structure.
• The reporting structure places this role within the UX leadership, likely reporting to a Director or VP of Design/UX.

Methodology:

• OpenTable emphasizes a data-driven approach, utilizing user insights and analytics to inform product development and design decisions.
• The company values collaboration and iterative improvement, as evidenced by the focus on optimizing processes and ways of working.
• A strong emphasis is placed on creating exceptional user experiences that drive value for both restaurants and diners.
• The culture is rooted in hospitality, extending to how employees are treated and how teams work together.

Company Website: https://www.opentable.com/ and https://opentable.design/

📝 Enhancement Note: OpenTable's position as a leader in restaurant reservations, coupled with its parent company's scale, suggests a robust operational infrastructure and a focus on scalable solutions. The emphasis on hospitality within the company culture is a key differentiator and should inform how candidates approach their interactions and demonstrate their fit.

📈 Career & Growth Analysis

Operations Career Level: Senior Management / Leadership This role represents a significant step into senior leadership within the product design discipline. It requires not only expert-level design skills but also the ability to manage, mentor, and strategically guide a team. The scope extends to influencing product strategy and operational excellence within the UX function.

Reporting Structure: The Senior Product Design Manager will likely report to a Director or VP of Design/UX. They will directly manage a team of product designers, and collaborate extensively with peer managers in Product Management and Engineering, as well as broader UX functions like Research and Design Systems.

Operations Impact: This role has a direct impact on OpenTable's success by ensuring that the restaurant-facing platforms are intuitive, efficient, and valuable. High-quality design for CRM, Guest Data, and Platform teams directly contributes to restaurant partner retention, operational efficiency, and ultimately, revenue. By optimizing these experiences, the role directly influences the productivity and satisfaction of OpenTable's B2B customer base.

Growth Opportunities:

• Operations Skill Advancement: Deepen expertise in B2B product design, platform strategy, and managing global design teams. Opportunities to lead larger initiatives or expand scope to new product areas.
• Leadership Development: Formal leadership training, mentorship programs, and "Development Dollars" to acquire new skills or certifications relevant to management and strategy. Potential progression to Director-level roles.
• Cross-functional Influence: Increased involvement in strategic product planning, business operations, and influencing the overall direction of OpenTable's B2B offerings.
• Industry Specialization: Further develop expertise within the unique challenges and opportunities of the hospitality and restaurant technology sectors.

📝 Enhancement Note: The career growth opportunities are framed to appeal to ambitious operations leaders. The emphasis on developing management skills, strategic influence, and industry specialization provides a clear path for advancement.

🌐 Work Environment

Office Type: Hybrid work model, with an expectation of 2 days per week in the downtown Toronto office. The initial phase may be remote. Office Location(s): Downtown Toronto, Canada.

Workspace Context:

• The Toronto office is likely designed to foster collaboration, innovation, and team cohesion.
• As part of a global company, expect access to modern design tools, collaboration platforms, and a strong emphasis on digital communication.
• The hybrid model balances the benefits of in-person interaction for team building and strategic discussions with the flexibility of remote work for focused individual tasks.

Work Schedule:

• A standard 40-hour work week is expected. However, due to the global nature of the teams and restaurant partner interactions, there will be a need for flexibility to attend meetings or respond to urgent matters outside of standard business hours. This is a common characteristic of global operations and leadership roles.

📝 Enhancement Note: Understanding the hybrid expectation and the need for schedule flexibility is crucial for operations professionals who often manage processes that span time zones and require responsiveness. The Toronto location offers access to a vibrant tech and business hub.

📄 Application & Portfolio Review Process

Interview Process:

1. Initial Screening: A recruiter will review your application and resume, focusing on alignment with the core requirements and operational experience.
2. Hiring Manager Interview: A conversation with the hiring manager (likely a Director/VP of UX) to assess your leadership style, strategic thinking, design philosophy, and fit with the team's culture. Expect questions about your experience managing designers and driving process improvements.
3. Portfolio Presentation & Design Deep Dive: A dedicated session where you present your portfolio, focusing on 2-3 key case studies that highlight your leadership, B2B design expertise, and impact. This will involve detailed discussions about your process, decision-making, and how you've managed complex challenges.
4. Cross-functional Interviews: Meetings with peers from Product Management, Engineering, Research, and Data Science. These interviews will assess your collaborative skills, ability to build consensus, and understanding of cross-functional dynamics in a product development setting.
5. Final Interview/Executive Round: Potentially a meeting with a senior leader (e.g., VP or C-level) to discuss strategic vision, company alignment, and overall leadership potential.

Portfolio Review Tips:

• Focus on Leadership & Process: Showcase your ability to lead teams, mentor designers, and optimize design workflows. Highlight how you've improved efficiency and quality within a design organization.
• B2B & Platform Emphasis: Select case studies that demonstrate your experience with complex B2B platforms, CRM, or data-centric products. Clearly articulate the business problems you solved and the impact on restaurant partners.
• Data-Driven Rationale: For each case study, explain how data (user analytics, A/B tests, market research) informed your design decisions and how you measured success. Quantify impact wherever possible (e.g., improved conversion rates, reduced support tickets, increased user adoption).
• Storytelling: Structure your presentations like a narrative – problem, your role/approach, solutions, results, and learnings. Be prepared to discuss trade-offs and challenges encountered.
• Cultural Fit: Be ready to articulate your leadership philosophy, collaboration style, and how you embody OpenTable's values of hospitality and continuous improvement.

Challenge Preparation:

• Expect potential scenario-based questions or a small design exercise focused on a B2B challenge relevant to OpenTable's business.
• Prepare to discuss how you would approach a specific design problem, how you would involve your team, and what metrics you would use to evaluate success.
• Practice articulating your thought process clearly, concisely, and persuasively.

📝 Enhancement Note: The interview process is structured to evaluate leadership, strategic thinking, and practical design execution within a B2B context. Candidates should prepare to demonstrate not just design skills, but also operational leadership and a data-driven mindset.

🛠 Tools & Technology Stack

Primary Tools:

• Design & Prototyping: Figma, Sketch, Adobe Creative Suite (Photoshop, Illustrator), InVision, Axure RP (or similar prototyping tools).
• Project Management & Collaboration: Jira, Confluence, Asana, Trello, Slack, Microsoft Teams.
• Design Systems: Familiarity with establishing, maintaining, and scaling design systems (e.g., Storybook, Zeroheight).

Analytics & Reporting:

• Web Analytics: Google Analytics, Adobe Analytics.
• Product Analytics: Mixpanel, Amplitude, Heap.
• Data Visualization/BI Tools: Tableau, Power BI, Looker (for understanding data trends and informing design).

CRM & Automation:

• CRM Systems: Salesforce (likely for internal sales/marketing operations), or understanding of how CRM principles apply to B2B user data.
• Customer Data Platforms (CDP): Familiarity with how customer data is managed and utilized.
• Automation Tools: Understanding how design integrates with automation workflows in B2B SaaS products.

📝 Enhancement Note: While this is a design role, a strong understanding of the technology stack used for CRM, data analytics, and product management is crucial for a Senior Manager in this space. It indicates the need for a candidate who can collaborate effectively with technical teams and understand the operational impact of design decisions on data and automation.

👥 Team Culture & Values

Operations Values:

• Hospitality: A core value that extends to how the team treats its members, partners, and users. This translates to empathy, excellent service, and a focus on creating positive experiences.
• Data-Driven: Decisions are informed by data and user insights, fostering a culture of continuous learning and objective evaluation of design solutions.
• Collaboration: Strong emphasis on teamwork, open communication, and shared ownership across product, engineering, and design.
• Innovation: Encouraging creative problem-solving and exploring new ways to enhance the user experience and business outcomes.
• Ownership & Accountability: Taking responsibility for outcomes, driving projects to completion, and being accountable for the impact of design decisions.

Collaboration Style:

• Cross-functional Integration: Designers are embedded within product teams, working closely with PMs and Engineers from inception to launch.
• Feedback-Rich Environment: Openness to constructive feedback and iterative design processes, valuing diverse perspectives.
• Knowledge Sharing: Encouraging the sharing of best practices, insights, and learnings across the design team and broader organization.
• Process Optimization: A proactive approach to identifying bottlenecks and improving workflows to enhance team efficiency and effectiveness.

📝 Enhancement Note: The emphasis on "Hospitality" as a core value is unique and important. Candidates should consider how this value translates into their leadership and design approach, especially when dealing with restaurant partners.

⚡ Challenges & Growth Opportunities

Challenges:

• Balancing Global Needs: Managing a global team and designing for diverse user needs across different markets requires careful consideration of cultural nuances and regional variations.
• Complex B2B Ecosystem: Designing for restaurants involves intricate workflows, diverse user roles (from owners to servers), and integration with various operational systems.
• Driving Adoption of New Features: Ensuring that restaurant partners understand, adopt, and effectively leverage new platform features requires strong user education and intuitive design.
• Navigating Ambiguity: Working within a large, evolving organization can present challenges in aligning priorities and navigating complex decision-making processes.
• Maintaining Design Quality at Scale: Ensuring consistent high-quality design across multiple platforms and product areas as the company grows requires robust processes and strong team leadership.

Learning & Development Opportunities:

• Advanced Design Leadership: Opportunities to hone skills in strategic planning, team building, and influencing organizational change.
• Industry Expertise: Deepen knowledge in the restaurant tech space, understanding the operational realities and business drivers of restaurant partners.
• Cross-functional Acumen: Develop a broader understanding of product management, engineering, and data science principles through close collaboration.
• Mentorship: Access to senior leadership for guidance and career development advice.
• Professional Development: Budget for conferences, workshops, courses, and certifications to stay current with design trends and leadership best practices.

📝 Enhancement Note: Identifying these challenges allows candidates to proactively prepare their responses and frame their experience as solutions, demonstrating foresight and problem-solving capabilities relevant to operations leadership.

💡 Interview Preparation

Strategy Questions:

• "Describe a time you had to establish a new design process or significantly optimize an existing one within your team. What was the challenge, your approach, and the outcome?" (Focus on process improvement, data, and team engagement).
• "How do you foster innovation and creativity within a design team, especially when working on established B2B platforms with complex user needs?" (Think about structured innovation, idea generation, and experimentation).
• "Tell me about a situation where you had to balance competing priorities from different stakeholders (e.g., Product, Engineering, Sales, Operations). How did you reach a consensus and ensure the best outcome for the user and the business?" (Emphasize negotiation, data-driven arguments, and cross-functional alignment).

Company & Culture Questions:

• "How do you embody the value of 'Hospitality' in your leadership and design approach, particularly when working with B2B clients?" (Connect empathy, user-centricity, and service-oriented thinking).
• "What is your experience working with global teams, and how do you ensure effective collaboration and inclusive design across different cultures and time zones?" (Highlight communication strategies, asynchronous work practices, and cultural sensitivity).
• "How have you used data and analytics to drive design decisions and measure the impact of your team's work on business objectives like restaurant partner retention or operational efficiency?" (Prepare specific examples with metrics and ROI).

Portfolio Presentation Strategy:

• Structure for Impact: Begin with a high-level overview of your leadership philosophy and approach to design management. Then, dive into 2-3 detailed case studies.
• Quantify Everything: For each case study, clearly state the problem, your team's role, the solution, and the measurable impact (e.g., % increase in user adoption, % decrease in errors, $ revenue impact).
• Highlight Leadership & Process: Emphasize your role in guiding the team, mentoring designers, and optimizing workflows. Show, don't just tell, how you manage and develop talent.
• Be Ready for Deep Dives: Anticipate detailed questions about your design decisions, the trade-offs you made, and how you would handle similar challenges in the future.
• Engage Your Audience: Make it a conversation. Ask clarifying questions, solicit feedback, and demonstrate your collaborative spirit.

📝 Enhancement Note: Preparing for these types of questions will allow candidates to showcase their operational mindset, strategic thinking, and leadership capabilities beyond just design execution.

📌 Application Steps

To apply for this Senior Product Design Manager position:

• Submit your application through the OpenTable careers portal via the provided link.
• Optimize Your Resume: Tailor your resume to highlight leadership experience, B2B product design, CRM/platform experience, team management, process optimization, and data-driven methodologies. Use keywords from the job description naturally.
• Curate Your Portfolio: Select case studies that best demonstrate your leadership, B2B design expertise, data-informed approach, and impact on business outcomes. Prioritize examples relevant to CRM, guest data, or platform design.
• Prepare Your Presentation: Practice presenting your portfolio, focusing on clear storytelling, quantifiable results, and articulating your leadership and process improvement contributions.
• Research OpenTable: Understand their mission, values, target audience (restaurants), and recent product developments. Familiarize yourself with their design philosophy at opentable.design.
• Anticipate Questions: Prepare thoughtful answers to common interview questions, especially those related to leadership, problem-solving, collaboration, and data utilization within a design context.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

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