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Senior Manager, Digital Delivery Enablement

Job in Toronto, Ontario, C6A, Canada
Listing for: RiseMe
Full Time position
Listed on 2026-09-27
Job specializations:
  • IT/Tech
    IT Project Manager, Change Management, Scrum Master, Business Systems & Technology Analysis
Salary/Wage Range or Industry Benchmark: 120000 - 160000 CAD Yearly CAD 120000.00 160000.00 YEAR
Job Description & How to Apply Below

Job Description What is the Opportunity?

In this role you will manage the development and execution of digital product strategies and projects of moderate complexity, ensuring alignment with business objectives and delivering value driven solutions. May oversee one or multiple teams in digital product management, driving strategic initiatives and resource optimization.

The Senior Delivery Enablement Manager is the operational backbone of the Workday platform, installing operational discipline and delivery infrastructure for predictable agile execution. This role owns how work moves efficiently through our pipeline—sprint optimization, backlog hygiene, release readiness, cross-domain dependencies, and delivery metrics—while product owners retain product decisions and roadmap prioritization.

Agile (Agile-like) Delivery
  • Facilitate sprint ceremonies (planning, stand-ups, backlog refinement, reviews, retrospectives).
  • Own sprint and release cadence end-to-end, including release calendars.
  • Maintain backlog hygiene in JIRA with well-formed stories and clear acceptance criteria.
  • Remove impediments blocking the team.
  • Coach product owners and leads on agile principles, adapted to HRDS operations.
Delivery Enablement & Governance
  • Own unified cross-team reporting template (Workday/JIRA and Service Now).
  • Report on team metrics and delivery health to leadership.
  • Manage cross-Platform dependencies.
  • Run release readiness and go/no-go processes for Workday changes.
  • Support execution of HRDS Operating Model and Support Model.
Team Enablement & Capability Building
  • Build delivery playbooks, templates, and standards.
  • Partner on resourcing and capacity planning.
  • Act as change agent for delivery maturity.
Stakeholder Communication
  • Serve as primary delivery point of contact for stakeholder visibility.
  • Present delivery status and metrics to leadership regularly.
  • Coordinate with Service Now and People Data & HRDS product owners and HRIT partners.
Success Metrics
  • Predictability: Consistent delivery against sprint and release commitments.
  • Transparency: Reporting template kept current and trusted by leadership.
  • Delivery Health: Workday Platform metrics tracked and acted on regularly.
  • Risk Management: Cross-Platform dependencies surfaced early with clean go/no-go decisions.
Required Experience
  • 7+ years in agile delivery, scrum mastery, or delivery/program management roles, with meaningful experience in an HR technology or enterprise SaaS platform environment.
  • Hands‑on experience with Workday and Service Now delivery cycles (configuration, integrations, releases, service updates) strongly preferred.
  • Proven track record running scrum ceremonies and agile delivery for a product team, not just administering a JIRA board.
  • Experience building or operating delivery metrics/reporting frameworks and communicating them to senior leadership.
  • Experience coordinating dependencies across multiple teams, vendors, or platforms.
Preferred experience
  • Prior people‑leadership experience, or clear readiness to hire and manage a small team.
  • Exposure to Service Now, SAP or other enterprise HR platforms, and to environments running multiple Platforms/products under one umbrella.
  • Certified Scrum Master (CSM), SAFe, or equivalent agile certification.
  • Experience operationalizing operating‑model artifacts (service catalogues, support models, stakeholder engagement models) into day‑to‑day delivery practice.
What’s in it for you?

We thrive on the challenge to be our best, progressive thinking to keep growing, and working together to deliver trusted advice to help our clients thrive and communities prosper. We care about each other, reaching our potential, making a difference to our communities, and achieving success that is mutual.

  • A comprehensive Total Rewards Program including…
Position Requirements
10+ Years work experience
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