Sr. Delivery Manager

Founded in 2017, Trip Arc is a $750 million privately held company that powers the top Travel Agencies and Tour Operators in North America with over $750 million in annual transactions. Our expansive network provides seamless access to a comprehensive range of travel options and services globally at industry‑best rates.

As an industry leader in technology, purchasing, finance, HR and marketing, we deliver solutions that meet travel professionals’ needs. With deep experience partnering with leading luxury travel brands Kensington Tours and Travel Edge, Trip Arc has real insight into the challenges of tour operators and agencies.

Trip Arc’s goals are simple: to make our network of more than 1,400 travel entities more profitable, efficient, and capable of creating truly unique travel experiences for their clients.

This is a hybrid position with currently 2 days per week onsite at our office located at 2 Queen St. E in Toronto, ON.

We are looking for a Senior Delivery Manager who drives change, coaches people, and holds delivery standards across multiple teams simultaneously. You will delve deep into each team’s work, surface problems before they become incidents, and build delivery muscle that elevates the entire organization. Coaching is central to this role; you will raise the delivery capability, identify growth opportunities, and model what good looks like in practice.

Trip Arc is in the midst of a mid‑SAFe adoption. Hands‑on SAFe experience and PI Planning expertise are strong assets, but we welcome candidates with deep delivery maturity and multi‑team leadership experience who are ready to embrace the framework.

Trip Arc develops AI‑powered products on an AI‑assisted delivery workflow. We expect our Senior Delivery Manager to be an advocate for both AI and people. You should understand how tools like Claude and other AI assistants transform velocity and quality, know what effective quality gates, review practices, and coaching look like in that context, and have experience leading delivery for AI‑assisted engineering teams.

• Facilitate all Scrum ceremonies across multiple parallel pods, including stand‑ups, backlog refinement, sprint planning, sprint reviews, and retrospectives.
• Investigate each team’s delivery reality, understanding what is built, what is at risk, and what is being avoided.
• Own SAFe activities such as PI Planning, coordinating across pods to align program increments, surfacing cross‑team dependencies, and maintaining delivery confidence at the portfolio level.
• Monitor sprint velocity, team capacity, and progress against goals; surface variance proactively 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 effective delivery hygiene.
• Drive retrospectives with genuine intent: diagnose root causes, assign action items, and follow up on actual change.
• Identify teams that are order‑takers rather than owners and actively shift that dynamic.
• Model what good delivery management looks like, raising the bar organization‑wide.

• Establish and enforce Jira ticket conformity across all teams; turn structured data 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…