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    Redwood Software

    Software Automation

    Technical Program Manager

    Ontario, CanadaOn-SiteFull-time5+ yrs experienceCA$125k – CA$150k / yearPosted 1mo ago
    All Redwood Software jobs

    Job description

    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 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

    YOUR IMPACT

    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

    YOUR EXPERIENCE

    • 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.

    Pay Transparency: The typical base salary range for this position is CAD $125,000 -$150,000 annually. The range represents base salary only, and does not include company bonus, incentive for sales roles, equity or benefits, as applicable. Final compensation will be determined based on the candidate's skills, experience, and relevant qualifications.

    Vacancy Status: Existing vacancy

    AI Transparency Disclosure: As part of our commitment to hiring transparency and in compliance with Ontario law, please be advised that we utilize artificial intelligence (AI) tools during our interview process. Specifically, we may use an AI-enabled notetaking assistant to help capture and summarize interview discussions. This tool is used solely to assist our hiring team in summarizing candidate information; all final hiring and selection decisions are made exclusively by individuals on the hiring team.

    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 [email protected]

    Job details are sourced from the employer's original posting.

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    About the company

    Redwood Software

    Redwood Software is the leader in full stack automation fabric solutions for mission-critical business processes. With the first SaaS-based composable automation platform specifically built for ERP, we believe in the transformative power of automation. Our unparalleled solutions empower you to orchestrate, manage and monitor your workflows across any application, service or server — in the cloud or on premises — with confidence and control.

    View all Redwood Software jobs
    Industry
    Software Automation
    Open roles
    39

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