Role Overview
The Director of Product Operations at Wrapbook is a remote role based in the US or Canada that owns the strategy, systems, and execution of how the engineering, product, and design organization delivers software. This position suits an experienced product operations leader with a strong background in technical program management who wants to build a predictable, high-throughput product engine powered by artificial intelligence.
Key Responsibilities
Own the end-to-end product development lifecycle, establishing the operating cadence, frameworks, rituals, and standards for discovery, planning, building, launching, and learning.
Manage the planning and intake operating cadence to turn roadmap priorities into structured, well-scoped, and ready-to-build work across engineering, product, and design.
Architect the release management approach, including tiered release programs, release-train cadences, and feature dial-up strategies that balance speed with stability.
Lead, manage, and grow a team of Technical Program Managers, setting high standards for execution, communication, and judgment.
Scale product quality through process, tooling, and AI rather than increasing user acceptance testing headcount, evolving the testing function to design systems that enable confident shipping.
Drive cross-functional alignment and transparent communication across business, product, and technical teams to ensure zero surprises for partners in client operations, go-to-market, and enablement.
Champion AI-powered ways of working by using agentic workflows and AI-assisted tooling to automate coordination, reporting, and process work.
Define metrics to measure delivery and release success, evaluating outcomes to continuously improve predictability, throughput, and stakeholder confidence.
Requirements
Minimum of 8 years of professional experience in product operations, technical program management, and/or release management within a SaaS environment.
Demonstrated people leadership experience, including directly managing, coaching, and growing teams of Technical Program Managers or QA professionals.
Solid foundational experience in technical program management combined with strong product sense and the ability to scale delivery systems.
Proven track record of building or maturing a product operations or delivery function from the ground up rather than just working within pre-existing frameworks.
Experience owning a release or delivery approach at scale, establishing strategy and standards for others to execute.
Driver's mindset focused on challenging assumptions, bringing structure to ambiguity, and valuing tangible outcomes over bureaucratic ceremonies.
Deep AI fluency and a growth mindset toward agentic workflows, with comfort using AI tools like Claude, Cursor, and Copilot.
Exceptional communication and facilitation skills to bridge departments, drive transparency, and maintain executive alignment.
Familiarity with modern program management and delivery tooling such as Linear and PagerDuty.
Bias for action in fast-paced, ambiguous environments paired with a genuine customer-obsessed approach.
Nice to Have
Experience building a Product Operations function completely from scratch at a previous organization.
A blend of experience at both larger and smaller scale-up companies, understanding both scaled excellence and ground-up creation.
Prior experience partnering directly with engineering, product, and design leadership to determine where Technical Program Managers drive maximum impact.
Background knowledge in payroll, fintech, entertainment, or union-based operating environments.
Skills and Tools
Technical Program Management
Product Operations and Release Management
SaaS Delivery Frameworks
AI Tools (Claude, Cursor, Copilot)
Linear and PagerDuty
Team Leadership and Mentorship
Cross-Functional Communication
Salary and Benefits
Annual salary range between $201,500 and $290,000 USD
Unlimited Paid Time Off
Remote work capability from anywhere in Canada and the United States
Comprehensive health and dental benefits
Up to $1,500 USD or $2,025 CAD towards home office IT setup
Up to 2% matching RRSP or 401K plan
Dedicated learning and development opportunities
Up to $50 USD or $67.50 CAD monthly towards internet and cell phone services
About the Company
Wrapbook provides a smart, intuitive platform that unifies production payroll, accounting, and project management for production teams, cast, and crew. Trusted by prominent production companies like SMUGGLER, Tuff, and GhostRobot, the company is backed by prominent investors including WndrCo, Andreessen Horowitz, and A* Capital with $130M raised. The growing team of over 250 professionals across the USA and Canada includes industry experts from entertainment and technology sectors.
How to Apply
To apply for this position, please submit your application directly on the official Wrapbook careers page.
