Sr. Delivery Manager

Range • Toronto, ON

9d • CA$110,000 - CA$125,000 • Hybrid

About The Position

At Range Group, we believe in the power of the professional travel advisor and represent over $4.5 billion in annual travel sales. Our investments are driven by the thesis that travel advisors add real value to a trip when equipped with technology and 24/7 support. The Range Foundation channels 10% of group profits to social impact initiatives. This is a hybrid position requiring 2 days a week onsite at our Toronto office.

We are seeking a Senior Delivery Manager to drive change, coach people, and uphold delivery standards across multiple teams. This role involves understanding team activities, proactively identifying and resolving problems, and building organizational delivery capability. Coaching is central, focusing on enhancing team delivery capabilities, identifying growth areas, and modeling best practices. Experience with SAFe adoption and PI Planning is a strong asset, though exceptional candidates with deep delivery maturity and multi-team leadership are encouraged to apply.

TripArc develops AI-powered products using an AI-assisted delivery workflow. The Senior Delivery Manager will advocate for these technologies, understanding how AI assistants impact team velocity and quality, and establishing effective quality gates, review practices, and coaching. Experience leading delivery for AI-assisted engineering teams is a plus.

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.
• Proven coaching ability: you have developed other delivery managers or Scrum Masters.
• 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.

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.
• Understand each team's delivery reality, including 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.
• 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, turning structured, consistent data into actionable insights.
• 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.
• Maintain a close working relationship with the Release Manager, aligning sprint outputs to release windows and ensuring nothing advances without appropriate oversight.

Benefits

• Competitive compensation package with a strong pay-for-performance rewards approach.
• Opportunity to participate in incentive programs and compensation tied to business and individual performance.
• Employment accommodation in accordance with the Ontario Human Rights Code and the Accessibility for Ontarians with Disabilities Act.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed