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Redwood

Enterprise automation SaaS for ERP tasks

Technical Program Manager

Program ManagementConfirmed live in the last 24 hours
Full-timeOntario, CanadaCA$125k - CA$150k /yrIn-person

About the Job

Requirements

  • A bachelor's degree in Electrical Engineering, Computer Science, Information Technology, or a related field, or equivalent experience.
  • At least five years of experience in Technical Program Management, Delivery Leadership, Consulting, or a similar high-impact role; enterprise or SaaS product experience is preferred.
  • Experience operating in multi-team SaaS and on-premises product environments.
  • Demonstrated success managing complex enterprise software releases.
  • A strong foundational understanding of the Software Development Lifecycle (SDLC).
  • Advanced proficiency in Jira, including workflow configuration, dashboards, and reporting automation.
  • Ability to dive 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 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 facilitate Go/No-Go decisions.
  • Ensure technical, operational, and customer enablement components are ready for launch.
  • Track and report release risk indicators, including defects, rollback risk, and deployment health.
  • Improve 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.
  • Use AI tools to automate delivery workflows, reduce manual reporting overhead, and improve operational efficiency.
  • 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 stakeholders have accurate, timely visibility into delivery commitments and release status.
  • Represent the engineering delivery organization in customer- and client-facing conversations when 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.
  • Assess, evolve, and implement delivery processes to meet changing product-line needs and maturity.
  • Identify bottlenecks, inefficiencies, and gaps in current workflows and drive targeted improvements with measurable outcomes.
  • Introduce and embed lightweight governance frameworks that scale with the team without unnecessary overhead.

Desired Qualifications

  • Experience with enterprise or SaaS products.
  • Agile or SAFe certifications.

About the Company

Redwood

Enterprise automation SaaS for ERP tasks

Redwood provides cloud-based automation software for enterprises. It offers three main products: finance automation to eliminate repetitive ERP tasks in back-office processes, workload automation to let IT teams schedule and manage jobs in the cloud while migrating from older tools, and report distribution to automatically deliver essential reports to the right people at the right time. These products work as a subscription-based service, where customers use the software platforms and can add premium support and consulting to optimize automation. Redwood differentiates itself by targeting large and multinational organizations with integrated, end-to-end automation across ERP, finance, and reporting, plus flexible cloud-based delivery and migration support from legacy systems. The company’s goal is to help businesses run more efficiently, cut manual work, reduce costs, and redeploy resources toward higher-value activities.

Company size
501-1,000
Company stage
Growth Equity (Venture Capital)
Total funding
$346.5M
Headquarters
Frisco, TX
Founded
1993

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