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.
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