Technical Program Manager

Redwood Software•Ontario, Canada, ON

About The Position

We are hiring a high-impact Technical Program Manager (TPM) to own end-to-end delivery health within a product area. This is a senior role embedded within a core product engineering group. You will partner with the Engineering Directors as your peer enabling engineering leaders to focus on technical quality while the TPM will own planning, governance, and stakeholder visibility and be the critical link ensuring our roadmap commitments translate into high-quality, enterprise-ready releases. You will operate at the intersection of Product, Engineering, Platform, Support, and Go-To-Market teams, and be directly accountable for delivery predictability, release readiness, dependency management, and executive visibility. This role demands a combination of strategic systems thinking and hands-on technical execution.

Requirements

Bachelor’s degree in Electrical Engineering, Computer Science, Information Technology, or a related field or equivalent experience
5+ years of experience in Technical Program Management, Delivery Leadership, Consulting, or a similar high-impact role, preferably in enterprise, SaaS products
Proven experience operating within multi-team SaaS and On-prem product environments.
Demonstrated success in managing complex, enterprise software releases, preferably Agile or SAFe certifications.
A strong, foundational understanding of the modern Software Development Lifecycle (SDLC).
Advanced proficiency in Jira (workflow configuration, dashboards, and reporting automation).
Comfortable diving deep into release details, technical tradeoffs, and deployment plans.
Experience building complex delivery dashboards and portfolio health reporting.
Strong data literacy and ability to translate metrics into actionable insight.

Responsibilities

Drive roadmap milestone tracking and confidence reporting for all initiatives.
Lead "path-to-green" recovery planning for at-risk programs to restore predictability.
Identify, manage, and mitigate cross-team and platform dependencies.
Ensure alignment between scope, sequencing, and engineering capacity.
Lead high-stakes release readiness reviews and Go/No-Go facilitation.
Ensure all necessary technical, operational, and customer enablement components are ready for launch.
Track and report on release risk indicators (defects, rollback risk, deployment health).
Drive continuous improvement of release processes to enhance enterprise reliability.
Design and optimize Jira workflows, delivery dashboards, and reporting systems.
Build and maintain milestone, dependency, and risk tracking tools.
Create executive-ready reporting based on data, not anecdotes.
Hands-on experience using AI tools to automate delivery workflows, reduce manual reporting overhead, and improve operational efficiency
Proactively use AI to detect delivery risk patterns and improve release documentation workflows.
Own cross-functional stakeholder communication across Product, Engineering, Sales, Customer Success, and Support
Ensure all parties have accurate, timely visibility into delivery commitments and release status.
Represent the engineering delivery organisation in customer and client-facing conversations where expectation setting is required.
Produce clear, forward-looking delivery health updates for senior leadership.
Present detailed risk heatmaps and mitigation plans to executives.
Partner with Engineering Directors on key engineering health metrics.
Continuously assess, evolve, and implement delivery processes to reflect the changing needs and maturity of each product line
Identify bottlenecks, inefficiencies, and gaps in current ways of working and drive targeted improvements with measurable outcomes
Introduce and embed lightweight governance frameworks that scale with the team without adding unnecessary overhead