Delivery Manager

TripArc•Toronto, ON

7h•$110,000 - $115,000•Hybrid

About The Position

TripArc is in active build mode with three pods (Itineraries on ADX, QT Styler, and Product Builder) delivering in parallel against a platform that thousands of travel advisors depend on daily. This Delivery Manager role is crucial for maintaining coherence across these pods, ensuring ceremonies are efficient, dependencies are identified early, teams are unblocked, and both teams and leadership are accurately informed. The role requires precision in execution, focusing on ensuring the right work is sequenced correctly across three teams with distinct rhythms and technical contexts. The Delivery Manager will serve as the operational backbone of this strategically important initiative. The ideal candidate will possess deep Scrum mastery, experience in cross-team delivery, and the professional maturity to effectively engage with engineering, product, and business stakeholders. TripArc utilizes AI-powered products and an AI-assisted delivery workflow, and the Delivery Manager is expected to be a strong advocate for both. This includes understanding how AI tools like Claude impact team velocity and quality, and establishing effective quality gates, review practices, and coaching in that context. Familiarity with Claude is expected, and candidates with experience leading delivery for AI-assisted engineering teams and building operational frameworks around such experience will be highly regarded.

Requirements

5+ years of experience as a Scrum Master or Delivery Manager, with demonstrated success leading multiple concurrent teams.
Deep, applied Scrum fluency — the judgment to adapt ceremonies and practices appropriately, not simply execute them by the book.
Advanced proficiency in JIRA and Git — ability to extract meaningful signals from delivery data and 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.
Demonstrated experience working across Product and Technology stakeholders in a complex organizational environment.
Experienced professional presence to coach upward as well as downward.
Familiarity with Claude (Alternative AI familiarity expected).

Nice To Haves

SAFe certification (SA, SSM, or equivalent) with hands-on PI Planning experience strongly preferred; CSM or PSM also valued.
Experience leading delivery for teams operating with AI-assisted development tooling.
Background in software development or quality assurance — an understanding of the technical realities your teams navigate.

Responsibilities

Facilitate all Scrum ceremonies across Itineraries on ADX, QT Styler, and Product Builder (stand-ups, backlog refinement, sprint planning, sprint reviews, retrospectives).
Own SAFe Agile 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, proactively surfacing variance with clarity.
Manage release plans in deep collaboration with the Release Manager and Product Owners, maintaining accuracy across scope, release numbers, and launch dates.
Own and maintain risk and decision trackers; identify blockers and surface dependencies before they impede delivery.
Chair team meetings, manage day-to-day project activities, and ensure appropriate escalation pathways are in place.
Establish and enforce JIRA ticket conformity across all teams, turning structured data from JIRA and Git into actionable insights.
Analyze data from JIRA and Git to identify patterns, forecast risks, and surface insights, ensuring dashboards and trackers 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.
Work cross-functionally to remove impediments, resolve conflicts, and develop actionable risk mitigations.
Lead Scrum of Scrums to surface and resolve cross-pod dependencies before they become delivery risks.
Partner with Product Owners to ensure business objectives are reflected in delivery sequencing.
Maintain a close working relationship with the Release Manager, aligning sprint outputs to release windows, coordinating cross-pod timing, and ensuring appropriate oversight.
Lead retrospectives with genuine intent to drive meaningful improvement.
Coach teams and Product Owners on Scrum best practices and AI-native ways of working.
Cultivate an environment of constructive conflict resolution and early problem visibility.
Identify and implement process improvements that increase throughput and delivery quality without compromising team sustainability.