Sr. Delivery Manager

Range•Toronto, ON

4h•CA$110,000 - CA$125,000•Hybrid

About The Position

We are looking for a Senior Delivery Manager who drives change, coaches people, and holds the delivery standard across multiple teams simultaneously. You will go deep into what each team is actually doing, surface problems before they become incidents, and build the kind of delivery muscle that makes the whole organization more capable overtime. Coaching is central to this role. You will raise the delivery capability of the teams around you, identify where people need to grow, and model what good looks like in practice. TripArc is mid-SAFe adoption. Hands-on SAFe experience and PI Planning expertise are a strong asset. That said, we welcome exceptional candidates who bring deep delivery maturity and multi-team leadership experience and are ready to embrace the framework. TripArc develops AI-powered products on an AI-assisted delivery workflow. We expect our Senior Delivery Manager to be a genuine advocate for both. That means understanding how tools like Claude and similar AI assistants change the velocity and quality dynamics of a development team, and knowing what effective quality gates, review practices, and coaching look like in that context. Candidates who have led delivery for AI-assisted engineering teams will stand out.

Requirements

7+ years of experience as a Delivery Manager or Senior Scrum Master, with demonstrated success leading multiple concurrent teams
A track record of driving real change in delivery culture, not just facilitating ceremonies. You can describe specific teams you improved, specific behaviors you changed, and how you measured it
Proven coaching ability: you have developed other delivery managers or Scrum Masters and can speak to what you did, not just that you did it
Deep, applied Scrum fluency with the judgment to adapt ceremonies and practices appropriately rather than executing them by the book
Advanced proficiency in Jira: you extract meaningful signals from delivery data and know how to translate them into actions
Proven capacity to manage cross-team dependencies and communicate risk escalations without generating unnecessary noise
Exceptional facilitation and conflict resolution skills, with the confidence to hold difficult conversations and drive alignment
The professional presence to coach upward as well as downward: senior stakeholders require delivery clarity, not delivery theatre

Nice To Haves

SAFe certification (SA, SSM, or SAFe Agilist) with hands-on PI Planning experience is strongly preferred; strong candidates with equivalent scaled delivery experience and willingness to certify are also welcome
Experience coaching a delivery team through a SAFe adoption or Agile transformation
Background in software development or quality assurance: understanding the technical realities your teams navigate makes you a better partner
Experience leading delivery for teams operating with AI-assisted development tooling
Familiarity with Claude or equivalent AI productivity tools

Responsibilities

Facilitate all Scrum ceremonies across multiple parallel pods, including stand-ups, backlog refinement, sprint planning, sprint reviews, and retrospectives
Go deep into each team's delivery reality, understand what is being built, what is at risk, and what is being avoided
Own SAFe activities including PI Planning, coordinating across pods to align program increments, surface cross-team dependencies, and maintain delivery confidence at the portfolio level
Monitor sprint velocity, team capacity, and progress against goals; surface variance proactively and with specificity, not just through reports
Manage release plans in close collaboration with the Release Manager and Product Owners, maintaining accuracy across scope, release versions, and launch dates
Own and maintain risk and decision trackers; identify blockers and surface dependencies before they impede delivery
Coach team members and delivery practitioners: identify capability gaps, support their growth, and raise the standard of delivery practice across the organization
Coach teams and Product Owners on Scrum best practices, AI-native ways of working, and what good delivery hygiene looks like in practice
Drive retrospectives with genuine intent: diagnose root causes, assign action items, and follow up on whether anything actually changed
Identify where teams are operating as order-takers rather than owners and actively shift that dynamic
Model what good delivery management looks like at a level that raises the bar across the whole organization
Establish and enforce Jira ticket conformity across all teams: structured, consistent data is the raw material; the expectation is that you turn it into actionable insights, not just dashboards
Analyze delivery data from Jira, leveraging AI tools including Claude to surface patterns, forecast risks, and translate numbers into meaningful insights that drive decisions
Translate reporting data into clear, insight-led status updates for teams and leadership, covering milestones, deliverables, dependencies, risks, and recommended actions
Collaborate with Product Owners to maintain prioritized backlogs, align delivery timelines, and manage competing demands across pods
Lead Scrum of Scrums to surface and resolve cross-pod dependencies before they become delivery risks
Work cross-functionally to remove impediments, resolve conflicts, and develop actionable risk mitigations
Maintain a close working relationship with the QA organization, ensuring quality gates are respected and QA is a structural part of the delivery process, not a downstream step
Maintain a close working relationship with the Release Manager, aligning sprint outputs to release windows and ensuring nothing advances without appropriate oversight