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Technical Program Manager

Redwood Software


Job Location:

Ontario - Canada

Monthly Salary: Not provided by the employer
Posted: 19 August 2026 (14 hours ago)
Application Deadline: 16 November 2026
Vacancies: 1 Vacancy

Job Summary

OUR MISSION

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 fabricwith AI embedded across the automation lifecycleRedwood 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 whats 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 Youll Bring

  • Bachelors 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

If you like growth and working with happy enthusiastic over-achievers youll 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


Required Experience:

IC