Head of Product & Delivery

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 builds software with K-12 school districts across North America.

We're looking for a Head of Product & Delivery to turn company priorities into shipped software, on the timelines that our districts are counting on.

Reporting to the CEO, you'll sit at the intersection of product, engineering, customers, and executive leadership. Our CEO and executive team set the vision and priorities. You'll own what it takes to deliver them: plans, estimates, timelines, stakeholder alignment, and accountability.

This is not a passive product role. We need a driver.

You'll ask hard questions, challenge assumptions, surface risk early, and make sure important commitments get met instead of quietly becoming new deadlines. You'll also build a team that owns its work, guided by trust and clear expectations that make high standards achievable.

What You'll Own

• Delivery plans:turning executive priorities into clear plans, owners, milestones, and committed dates.
• The backlog: one prioritized list, pulling in district feedback, support, and internal requests, aligned to company strategy.
• Estimates and timelines:challenging assumptions and pushing for the smaller version that ships sooner.
• Recovery when work slips:changing scope, sequencing, staffing, or approach before accepting a new date.
• Operating discipline: every meaningful task has an owner, an estimate, a deadline, tracked time, and SR&ED tagging where it applies.
• Delivery visibility:capacity, throughput, and performance, working with engineering leadership when output falls short.
• Stakeholder involvement: the right people in product decisions, from district staff to subject matter experts and senior leadership.
• Weekly reporting:what's on track, what's at risk, and what decisions are needed.
• The evolution of our pod development model: small, accountable teams given one business problem and the autonomy to solve it.

Leading People

• Lead and develop the product team with clear expectations, measurable goals, and regular, direct feedback.
• Recognize strong work, coach people who can grow, and address underperformance or missed opportunities early.
• Build leaders who own their outcomes, dates, and blockers without waiting to be asked.

AI and Agentic Development

AI is changing how software gets built, and this role leads that change on our team.

• Drive adoption of AI-assisted and agentic development across product and engineering.
• Set practical standards for how AI is used in planning, coding, testing, and delivery.
• Measure whether new tools improve productivity, velocity, and quality, and spread the workflows that do.
• Encourage teams that are thriving with new tools and processes, and support teams and individuals who need help catching up.

We measure our success by what we ship and how well it’s received.

What You Bring

• Significant experience leading product, delivery, or development teams.
• A strong track record of shipping complex software against meaningful deadlines.
• A proven track record in leading change management on a product or development team.
• The confidence to constructively challenge engineers, product managers, and executives.
• Experience using metrics to evaluate engineering performance and delivery risk.
• Deep, hands‑on understanding of AI-assisted and agentic development.
• Experience managing and developing product professionals.

Experience with K-12, enterprise, or public‑sector software is an asset.

The Person

You're accountable, commercially minded, technically credible, and action‑biased.

When something slips, your first question is why. Then: What's actually blocking us? What can we change? Who needs to act? How do we still get this done?

That's the mindset we're hiring for. If it sounds like you, we'd love to talk.