Technical Program Manager Ontario, Canada

Redwood; Canada; On-site; CAD 110,000 - 160,000; Full time

Job summary

Redwood is seeking a Technical Program Manager to own end-to-end delivery health within a core product area. You will partner with Engineering Directors to balance technical quality with roadmap commitments, driving planning, governance, and executive visibility across Product, Platform, and Go-To-Market teams.

You’ll lead roadmap tracking, recovery for at-risk programs, release readiness, and risk dashboards, while embedding AI tools to automate reporting and improve delivery efficiency.

Qualifications

• 5+ years of experience in Technical Program Management or delivery leadership.
• Experience in multi-team SaaS environments and enterprise software releases.
• Proficiency with Agile or SAFe frameworks.
• Strong understanding of the Software Development Lifecycle (SDLC) and release governance.

Responsibilities

• Own end-to-end delivery health within a product area and ensure roadmap commitments translate into releases.
• Lead release readiness reviews and Go/No-Go decisions.
• Design delivery dashboards, milestone tracking, and risk reporting.
• Manage cross-functional stakeholder communications across Product, Engineering, Sales, Customer Success and Support.
• Provide executive delivery health updates and risk mitigation plans.
• Drive continuous improvement of delivery processes at scale.

Skills

Delivery leadership

Stakeholder management

Data literacy

Strategic thinking

Multi-team SaaS

Education

Bachelor’s degree in Electrical Engineering, Computer Science, Information Technology, or related field

Tools

Jira

Job description

At Redwood, we empower our customers with lights-out automation for their mission-critical business processes. At Redwood, we empower our customers with lights-out automation for their mission-critical business processes.

ABOUT US

Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. Redwood Software is the leading orchestration platform for the autonomous enterprise, driving business transformation at the lowest total cost of ownership. Redwood empowers organizations to intelligently automate and orchestrate mission-critical business and IT processes across complex ERP, hybrid cloud, data and emerging agentic AI systems. Through its SaaS-first automation fabric—with AI embedded across the automation lifecycle—Redwood accelerates the path to autonomous operations. Backed by 30 years of experience and trusted by more than 50% of the Fortune 50, Redwood helps organizations unlock human potential to focus on innovation, growth and what’s next.

CORE VALUES

• One Team. One Redwood
• Make Your Own Weather
• Obsess over Customer Success
• Work the Problem
• Be Curious
• Own the Outcome
• Respect Each Other

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.

End‑To‑End Delivery & Program Health

• 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.

Release Governance & Readiness

• 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.

Technical Delivery Operations

• 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.

Cross Functional Stakeholder Management

• 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.

Executive Transparency

• 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.

Continuous Improvement & Process Evolution

• 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

What You’ll Bring

• 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.

THE LEGAL BIT

Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero tolerance policy applied to it.

Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at [e-mail]

If you like growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!

THE LEGAL BIT

Redwood is an equal opportunity employer. Redwood prohibits unlawful discrimination based on race, colour, religion, sex, gender identity, marital or veteran status, age, national origin, ancestry, citizenship, physical or mental disability, medical condition, genetic information or characteristics (or those of a family member), sexual orientation, pregnancy or any other consideration made unlawful by regional or local laws. We also prohibit discrimination based on a perception that anyone has any of those characteristics or is associated with a person who has or is perceived as having any of those characteristics. All such discrimination is unlawful and will have a zero tolerance policy applied to it.

Redwood will comply with all local data protection laws, including GDPR when it comes to the handling and processing of personal data. Should you wish for us to remove your personal data from our recruitment database, please email us directly at [e-mail]