Director of Product & Delivery

remote
Toronto, Ontario, Canada .
full-time . May 6, 2026

Description

Trew Knowledge is a fast-paced and rapidly growing digital marketing agency focused on delivering world-class, innovative solutions for some of the world’s largest Brands. As the only Canada based WordPress VIP Gold Agency Partner, we proudly deliver award-winning solutions that leverage our innovative vision, technical prowess, and unmatched customer service.

Our team of dedicated professionals align themselves with our clients’ particular business goals, through a holistic approach, creating digital development, brand strategy, and customer identity management solutions to take the customer’s brand to a higher level.

We are currently seeking a seasoned leader to fulfill the role of Director of Product and Delivery.

About the role

The Director of Product & Delivery is accountable for overseeing, leading, and managing a high-performing team throughout the full product development and delivery lifecycle. The role defines and drives product strategy, vision, and execution, ensuring alignment with client needs, market dynamics, and Trew Knowledge’s strategic direction. As a member of the leadership team, the Director of Product & Delivery contributes to the achievement of business strategy by driving product development and delivery goals to successful completion and effectively leading others toward the vision. The Director also plays a critical role in advancing the agency’s technological evolution, embedding AI and agentic approaches into product thinking, delivery models, and operational workflows. The role balances strategic product leadership with operational excellence in project delivery, ensuring that digital solutions are not only innovative and competitive, but also executed with rigour, efficiency, and measurable impact.

What you will do

Product Playbook, Strategy and Vision

Develop and maintain a Product Playbook aligned with best practices with clear documentation, communication standards, and scalable processes and frameworks that define how the product and project teams operate.
Develop and articulate a compelling product vision and strategy that is aligned with the agency's mission and strategic objectives, market trends, client needs, and the WordPress environment.
Conduct market research, competitive analysis, and customer feedback sessions to identify product differentiation and growth opportunities.
Define and prioritize product roadmap initiatives based on market dynamics, client needs, and business objectives.
Integrate AI-native and agentic design principles into product strategy and discovery, identifying opportunities to enhance client solutions, internal efficiency, and innovation.

Product Development and Execution

Collaborate closely with cross-functional teams, including executive leaders, design, engineering, project management, and marketing and sales, to translate the product vision into actionable plans for the Product and Delivery team.
Oversee the end-to-end product development and delivery lifecycle, ensuring alignment between product strategy, project execution, timelines, and resource allocation.
Implement agile product management methodologies and best practices to ensure efficient execution, rapid iteration, and timely delivery of high-impact features and enhancements.
Ensure strong delivery governance, including scope, timelines, resource planning, and risk management across all active initiatives.
Identify and implement opportunities to leverage AI and automation within product development and delivery workflows to improve speed, quality, and scalability.

Client Engagement and Relationship Management

Act as a strategic advisor to key clients, aligning product direction and delivery with their business objectives, and guiding them on opportunities related to digital transformation, including AI-driven solutions.
Partner with account management and other key stakeholders to identify client needs, gather feedback, and drive upsell opportunities based on product capabilities.
Build and nurture strong client relationships through effective communication, collaboration, and proactive support.

Performance Monitoring and Optimization

Define and monitor key performance indicators (KPIs) related to product performance, delivery effectiveness, user engagement, and client satisfaction.
Leverage data, user feedback, and market insights to continuously optimize product features, user experience, and delivery processes.
Drive continuous improvement across product and project workflows to enhance efficiency, scalability, and overall performance.

Leadership and Team Management

Lead, mentor, and inspire a small team of Project Managers and Product Owners to drive innovation and excellence in product development while fostering a culture of collaboration, creativity, and continuous improvement.
Support the evolution of team capabilities in emerging areas, including AI-enabled product thinking and delivery practices through continuous learning.
Provide guidance, feedback, and support to empower direct reports to achieve their full potential and deliver high-quality results.
Collaborate with Human Resources on Product team talent acquisition, talent management, professional development and other people management activities.
Set clear goals and objectives, manage and evaluate individual performance, and perform other people management activities as defined.

What you need to qualify

Education and Experience

Bachelor's or Master's degree in business, marketing, computer science, or a related field
8-10 years of experience in product management or related roles
At least 5 years of experience in a leadership role with direct reports and/or managing others within a project team environment
Experience in an agency environment (marketing, advertising, or digital) is an asset
Client-facing or client services experience is an asset.
Experience working in an agile or hybrid environment, with high proficiency in agile methodologies and tools.
Certifications such as CSPO, PMP or PMI are a strong asset
Strong experience with WordPress at the enterprise level, including being active in the WordPress Community

Competencies, Knowledge and Skills

Proven track record of leadership and team management, with the ability to inspire and empower cross-functional teams.
Strong strategic thinking, analytical / problem-solving skills, and business acumen, with the ability to translate market insights into actionable product strategies.
Excellent communication, presentation, and interpersonal skills, with the ability to engage with clients, stakeholders, and team members at all levels.
Passion for innovation, technology, and driving customer success through exceptional product experiences.
Proficient knowledge and understanding of information technology platforms and integrated systems
Proven track record taking products from 0 to 1, owning concept through launch.
Demonstrated experience integrating AI into product, delivery, or operational workflows, with measurable impact on efficiency, quality, or client outcomes.

What success looks like in this role

Success in this role will be measured by the Director’s ability to effectively balance strategic product leadership with operational excellence in delivery, while contributing to Trew Knowledge’s evolution as an AI-native agency.

Within the first 6–12 months, success will include:

Clarity and Alignment: Establishing a clear and actionable product vision and roadmap, with strong alignment across Product, Project Management, Engineering, Design, and Leadership.
Delivery Excellence: Ensuring consistent, predictable, and high-quality delivery across projects, with improved visibility into timelines, resourcing, and risks.
Team Performance and Growth: Building a high-performing, engaged team of Product Owners and Project Managers, with clear expectations, strong accountability, and ongoing development.
Client Impact and Satisfaction:Strengthening client relationships by acting as a trusted advisor, contributing to high client satisfaction, retention, and identification of growth opportunities.
Operational Maturity: Enhancing and scaling product and project management practices, including playbooks, processes, and governance, to improve efficiency and consistency across engagements.
AI-Native Advancement: Identifying and implementing meaningful opportunities to integrate AI and agentic approaches into both client solutions and internal workflows, driving innovation and measurable impact.

What we offer

Remote work and work-life balance
Competitive compensation package
Career development and growth
Generous paid time off (vacation, sick days, personal time, etc)
Group insurance coverage (for people located in Canada) including extended health, dental, vision and travel
A MacBook Pro Laptop and up to $1000 allowance for home office equipment
A learning & development yearly budget of $500
A dynamic team of individuals who are passionate about what they do and who are eager to welcome you aboard!

Application Process

At Trew Knowledge, we embrace our diversity and inclusiveness, and we strive to create an environment where everyone feels valued, respected, and heard. We are committed to attract, develop, and retain our individuals without discrimination on any ground protected by applicable law, with the goal to create a strong team. We believe that a diverse workforce from all backgrounds with broad perspectives and creative ideas can benefit our clients, our partners and all of us as collaborators.

As part of our commitment to transparency and fairness, we would like to inform applicants that our recruitment process includes the use of artificial intelligence (AI) technology to screen applications. The AI system assists in evaluating resumes and cover letters to identify candidates whose skills and experiences align with the job requirements.

As much as we would like to be able to respond to every applicant, we will only contact the ones who qualify for an interview and wish to thank everyone for their interest in our business and available position.

Compensation

$125,000.00 - $130,000.00 per year

Know someone who would be a perfect fit? Let them know!