Technical Program Manager Jobs in Toronto, ON (NOW HIRING)

We're seeking a Technical Program Manager to drive cross-team execution across two critical Flex spaces: MELTS (Motivation, Evaluation, Learning, Transparency & Signals) and the Transporter Experience On Road Org (OTX).
MELTS builds the post-execution features that help delivery partners understand their performance, improve delivery quality, and stay engaged - including Standings, Achievements, Rewards, Promotions, and the Learning Portal. OTX owns the on-road experience and shipper contracts & execution systems, equipping transporters with the tools and guardrails to complete deliveries, pickups, and services efficiently and at high quality while powering the backend systems and contract constructs that underpin all of Last Mile.
You'll split your time across both spaces coordinating programs across five engineering teams (SMART, Evaluation, Motivation, DELTA, and Lapin) and their distributed service architectures. On OTX, you'll work directly with mobile and backend engineers across multiple tech teams to enhance on-road experiences, improve transporter quality, and evolve execution systems

You'll own program roadmaps, manage cross-team dependencies, surface risks early, and drive alignment between engineering, program, product, and science stakeholders.
The ideal candidate is comfortable navigating ambiguity, making tradeoffs between speed and quality, and communicating clearly with both technical and non-technical audiences. You'll also be expected to deep dive into the vast Last Mile Service landscape to identify signal sources from partner teams. Experience with large-scale distributed systems, data pipelines, or ML-driven evaluation platforms is a plus

Past software engineering or software architecture experience is highly recommended for this role.
Key job responsibilities
- Partner with engineering, product, and program teams to identify and evaluate signal sources from upstream Last Mile teams used for driver defect and exemption attribution.
- Leverage familiarity with big data systems and technical architectures to navigate complex service dependencies and inform program decisions.
- Create and maintain program roadmaps that align cross-team priorities across MELTS and Transporter Experience.
- Own and run weekly program reviews, ensuring visibility into progress, risks, and blockers across all active workstreams.
- Drive project execution end-to-end - tracking milestones, surfacing risks early, removing blockers, and holding teams accountable to commitments.
- Author flashes and program review documents that clearly communicate status, impact, and escalations to leadership.
- Build strong working relationships with partner teams across the Last Mile organization to enable effective cross-team collaboration and dependency management.
- Earn trust with senior management through regular, transparent communication on program status, risks, and change control.
- Partner with managers and stakeholders to secure resources, scope engineering efforts, set project priorities and milestones, and drive on-time delivery.
- Ensure end-to-end quality by managing feature testing, enforcing quality definitions, coordinating releases, and overseeing post-launch monitoring.
- Drive the management of large, complex cross-functional programs with significant business impact - defining strategy, setting objectives, and analyzing data to quantify improvements.
A day in the life
Your morning might start by reviewing program metrics and preparing a flash update for leadership. By mid-morning, you're running a cross-team sync with SMART and Evaluation engineers to unblock a dependency on a new defect signal

After lunch, you're partnering with a product manager to scope a Standings feature launch in a new locale, then jumping into a deep dive with an upstream team to evaluate a new data source for exemption attribution. Later, you join an OTX sprint review to track progress on an on-road delivery flow improvement and align with mobile engineers on an upcoming release. You'll end the day updating your program roadmap and flagging risks ahead of tomorrow's weekly program review.
About the team
Flex MELTS (Motivation, Evaluation, Learning, Transparency & Signals) is a team within Amazon's Last Mile organization focused on helping delivery partners succeed

We build the post-execution systems that evaluate driver performance, provide near real-time feedback, and power features like Standings, Achievements, Rewards, Promotions, and the Learning Portal. Our work spans five engineering teams - SMART, Evaluation, Motivation, DELTA, and Lapin - operating across distributed service architectures and ML-driven evaluation models. We believe transparency builds trust, and we're committed to ensuring delivery partners always know where they stand and what they can do to improve.
This role also partners closely with the Transporter Experience On Road Org (OTX), which owns two charters: On-Road Experience and Shipper Contracts & Execution Systems

The On-Road team maximizes efficiency, quality, and capability across all on-road tasks - delivery, pickup, and services - equipping transporters with tools to complete work quickly without sacrificing quality, while serving as the transporter's advocate for a superior quality of day. The Shipper Contracts & Execution Systems team powers all on-road experiences and fundamental contract constructs for all of Last Mile, including backend and processing systems.
Together, MELTS and OTX impact millions of drivers worldwide across the full transporter lifecycle - from on-road execution to post-delivery evaluation and growth.