Product Operations Director

Applied Systems Canada•,

10h•CA$150,000 - CA$190,000•Remote

About The Position

The Product Operations Director leads how the product organization applies AI to its work, owns the tooling and infrastructure used by product teams, and stewards the operating system that connects customer insight to delivered outcomes. The role makes these practices repeatable, measurable, and adopted. The director sets AI enablement strategy, standards, and governance for Product and Engineering; owns shared AI tools, skills, connectors, automations, and training; and measures adoption and impact. The role is accountable for the product operations infrastructure and tooling portfolio, including integrations, data flows, dashboards, tool architecture, adoption, ROI, vendor relationships, and tenant-level configuration and access governance. The director maintains the product operating system with Product and Engineering leadership, leads its adoption and change management, and standardizes how work moves through the product lifecycle. The role also builds measurement infrastructure for operating-level and ways-of-working metrics, in coordination with the Portfolio Strategy Director. This is a remote role with an anticipated annual compensation range of $150,000–$190,000 CAD. Starting compensation depends on role scope and the successful candidate’s relevant experience, skills, and location.

Requirements

12+ years of professional experience, including 10+ years in product operations, product management, program management, and/or project management.
Experience enabling teams with AI tools and workflows, including agents, skills, connectors, and automations; governing their use; and demonstrating measurable efficiency or quality impact.
Experience owning tools end to end, including strategy, implementation, adoption, ROI, vendor negotiation, and contracts.
Ability to design and run integrated tooling infrastructure, including data flows, dashboards, and system integrations.
Experience building operating models and repeatable processes and leading the change management needed for adoption.
Ability to lead through influence without positional authority and credibility with engineers, product leaders, and C-suite stakeholders.
Strong written and data-based communication skills, and willingness to retrieve and analyze data when a ready-made report is unavailable.
Ability to facilitate high-stakes cross-functional discussions and drive them to decisions.
Genuine curiosity about insurance technology.

Nice To Haves

Ability to launch a product-team AI skill registry and connector standards, define access and data governance, and establish adoption and impact measures.
Ability to define a multi-subscription Pendo architecture and 2027 budget, map integrations across the product stack, and set vendor strategy.
Ability to take the operating system from draft to version 1, run working groups, publish minimum-spec and launch-readiness templates, and support initial team adoption in Q1 2027.
Ability to turn the cross-functional customer feedback process into a standing mechanism that informs annual allocation and planning with clear drivers, inputs, and outcomes.

Responsibilities

Lead AI enablement for product teams by setting strategy, standards, and governance; managing the skill registry, connectors, shared automations, tool selection, access and data guardrails, adoption measurement, and training.
Own product operations infrastructure, including integrations among analytics, roadmap, customer-feedback, and capability-mapping systems, along with related data flows, dashboards, and automations.
Set architecture, ownership, documentation, reliability, and AI-readiness standards for the product operations infrastructure.
Own the product tooling portfolio’s strategy, adoption, ROI, and outcomes, and decide where to build, buy, consolidate, or retire tools.
Govern tenant-level configuration and access, including subscription architecture, instrumentation and tagging standards, privacy and unmasking governance, access and provisioning, and usage and overage forecasting.
Manage vendors and contracts with Procurement, including negotiations, tool evaluations, vendor governance, quarterly business reviews, and evidence-based outcomes.
Maintain and version the product operating system with Product and Engineering leadership; lead working groups, adoption, and change management for the transition to 2027.
Own the central calendar, agenda and pre-read standards, and criteria for sunsetting ad hoc meetings; measure meeting load and retire meetings that do not provide sufficient value.
Establish a mechanism for sourcing cross-functional customer feedback from Sales, Support, CX, and Adoption into annual allocation and planning decisions.
Standardize product lifecycle practices through minimum-spec templates, launch-readiness scorecards, and telemetry and instrumentation standards; train product roles and support adoption.
Build data and dashboard infrastructure for metrics defined with the Portfolio Strategy Director, and own operating-level and ways-of-working metrics such as meeting load, template adoption, and telemetry coverage.
In the role’s initial scope, stand up AI enablement, define the tooling and infrastructure roadmap, move the operating system from draft to version 1, and establish the cross-functional customer feedback mechanism.