Head of Product & Delivery

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 CEO 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.
Spot the people and teams thriving with new methods, and support the ones who need help catching up.
We measure AI by what we ship: more high-quality software from the team we have.
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 challenge engineers, product managers, and executives, respectfully and constructively.
Experience using metrics to understand 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 biased toward action.
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.

Work arrangement
Yes