Product & Delivery Leader for AI-Driven Education

Imagine Everything; Canada; On-site; CAD 180,000 - 280,000; Full time

Job summary

Imagine Everything is seeking a Head of Product & Delivery to transform priorities into shipped software on North American district timelines. You will own plans, estimates, timelines, and accountability, while driving a team with trust and high standards.

This role requires leading product and delivery teams, advancing AI-assisted development, and enforcing disciplined delivery with clear ownership and metrics.

Qualifications

• Significant experience leading product, delivery, or development teams.
• Proven track record shipping complex software against meaningful deadlines.
• Experience leading change management on product or development teams.
• Ability to challenge engineers, product managers, and executives constructively.
• Experience using metrics to evaluate engineering performance and delivery risk.
• Deep hands-on understanding of AI-assisted and agentic development.

Responsibilities

• Translate executive priorities into clear plans, owners, milestones, and committed dates.
• Maintain a single backlog aligned to company strategy with district feedback.
• Develop estimates and timelines, pushing for incremental, shippable releases.
• Recover from slippage by adjusting scope, sequencing, staffing, or approach.
• Ensure accountability with owner, estimate, deadline, tracked time, and tagging where applicable.
• Provide delivery visibility with capacity and throughput in collaboration with engineering leadership.
• Involve the right stakeholders in product decisions from districts to senior leadership.
• Generate weekly reports on progress, risk, and decisions needed.
• Evolve our pod development model with small, accountable teams solving business problems.

Skills

Product leadership

Delivery management

Stakeholder management

AI adoption

Change management

Team development

Job description

Imagine Everything is seeking a Head of Product & Delivery to transform priorities into shipped software on North American district timelines. You will own plans, estimates, timelines, and accountability, while driving a team with trust and high standards.

This role requires leading product and delivery teams, advancing AI-assisted development, and enforcing disciplined delivery with clear ownership and metrics.