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ᓄᓇᕗᑦ Nunavut, Canada
Remote only
About Us:
Wrapbook is a smart, intuitive platform that makes production payroll and accounting easier, faster, and more secure. We provide a unified payroll platform that seamlessly connects your entire team—production, accounting, cast, and crew—all in one place. Wrapbook empowers production teams to manage projects, pay cast and crew, track expenses, and generate data-driven insights, while enabling workers to manage timecards, track pay, and onboard to new projects from any device. Wrapbook brings clarity and dependability to production payroll, while increasing the productivity of your whole team.
Trusted by companies of all sizes, Wrapbook powers payroll for some of the industry’s top production companies, including SMUGGLER, Tuff, and GhostRobot. Our growing team of 250+ people across the USA and Canada, including entertainment and technology experts from SAG-AFTRA, DGA, IATSE, Teamsters, Amazon, Microsoft, Facebook, and more. Wrapbook is backed by top-tier investors, including Jeffrey Katzenberg’s WndrCo, Andreessen Horowitz, and A* Capital. We have raised $130M and are in a strong financial position.
The Opportunity – Director, Product Operations (Remote - USA / CANADA)
We're looking for a Director of Product Operations to own how Wrapbook aligns, builds, and launches product. Product operations is the practice of how we actually deliver: the systems, rituals, and standards that turn a growing EPD org into a predictable, high-throughput product engine. You'll define that practice for Wrapbook and lead the team that runs it, with AI as the foundation.
This role sits within Wrapbook's Product & Design organization and reports directly to the Chief Product Officer. You'll own the end-to-end product development process: how work moves from idea to discovery, planning, build, launch, and learning, and you'll lead the teams and systems that make each stage predictable and repeatable. That spans the operating cadence and structure of product development requirements, our Technical Program Management practice, our approach to quality, and how we release (from our tiered release program to how features are dialed up into customers' hands). You architect and continuously evolve the system, while your TPMs own execution within their groups. Your job is to build the machine, raise the bar, and coach the team that runs it.
You'll be a driver, not a facilitator. Someone who challenges assumptions, pushes your team to do the same, and brings structure to ambiguity without drowning teams in process. Your impact will show up as more predictable delivery, better cross-functional alignment, measurable success criteria, and no surprises for our partners, because they'll always know what we're shipping and why.
AI is foundational to how you and your team work. You'll bring deep AI fluency and a bias toward agentic, automated workflows, using them to remove coordination overhead, accelerate release cycles, and let the team focus on higher-leverage problems.
If you're energized by owning a function end-to-end, building the operating system for a product org, and leading through both strategy and hands-on system design, this role is for you.
What You'll Do:
Own the end-to-end product development process. Define and mature how work moves from idea through discovery, planning, build, launch, and learning: the operating cadence, frameworks, rituals, tooling, and standards that make delivery predictable and scalable across Engineering, Product, and Design (EPD). This is the core of the role; everything below is in service of it.
Run the planning and intake operating cadence. Own how roadmap priorities move from discovery and requirements into structured, well-scoped, ready-to-build work across EPD, including prioritization, sizing, and sprint planning, so teams start each cycle with clarity and finish it with predictability.
Architect the release system (don't just run releases). Own Wrapbook's approach to release management, spanning our tiered release program, release-train cadence, and feature dial-up strategy, while balancing speed with stability. Set the standard and the guardrails; your TPMs own execution within their groups.
Lead and grow the TPM practice. Manage and develop a team of Technical Program Managers, setting a high bar for execution, communication, and judgment. Partner with EPD leaders to point TPMs at the highest-leverage work: strategic initiatives, complex cross-group coordination, and business-critical delivery.
Build the system around quality. Own how Wrapbook product scales quality through process, tooling, and AI rather than through ever-growing UAT headcount. Evolve our UAT function from doing the testing toward designing the systems and standards that let every team ship with confidence.
Drive alignment and impeccable communication. Be the connector across business, product, and technical teams, creating clarity on roles, readiness, risks, and decisions at every stage of build and launch. Over-communicate so cross-functional partners (Client Ops, GTM, PMM, Enablement) experience no surprises.
Champion AI-powered ways of working. Model and scale AI fluency across the team and the EPD org. Use agentic workflows and AI-assisted tooling to automate coordination, reporting, and process work, increasing throughput without adding headcount.
Measure and improve impact. Define how we measure delivery and release success, evaluate outcomes, and turn insight into durable improvements. You'll be measured not by the number of processes you introduce, but by the tangible impact on predictability, throughput, and stakeholder confidence.
What You'll Have:
8+ years in product operations, technical program management, and/or release management within SaaS.
Proven people leadership: experience directly managing, coaching, and growing a team (ideally Technical Program Managers and/or QA), with a track record of developing individuals, setting a high bar, and building an inclusive, high-accountability culture.
A TPM foundation with product sense: you've been close enough to how product gets built to have real judgment, and grew from there into owning operations and systems. (Pure QA or pure program-coordination backgrounds are typically not the right fit.)
A track record of building or maturing a product operations / delivery function: standing up the system, not just working within someone else's.
Experience owning a release or delivery approach at scale: setting the strategy and standards that others execute against, and balancing speed with stability.
A driver's mindset: you challenge assumptions, raise the bar, and bring structure to ambiguity without adding bureaucracy. You value outcomes over ceremonies.
Deep AI fluency and a growth mindset toward agentic workflows: comfort using AI tools (e.g., Claude, Cursor, Copilot) and a demonstrated ability to identify where automation meaningfully improves team output.
Exceptional communication and facilitation skills, with a proven ability to bridge departments, drive transparency, and keep executives and cross-functional partners aligned.
Experience with modern program management and delivery tooling (e.g., Linear, PagerDuty).
A bias for action in fast-paced, ambiguous environments, and genuine customer obsession.
Extra Points if You Have:
Built a Product Operations function from the ground up at a previous company.
A mix of larger and smaller / scale-up company experience: you've seen what "good" looks like at scale and know how to build it from scratch.
Experience partnering directly with Engineering, Product, and Design leaders to shape where and how TPMs drive impact.
Experience in payroll, fintech, entertainment, or union-based environments.
Why Join Us
At Wrapbook, creativity meets technology — and not just in the product.
In addition to a competitive salary and all the benefits you can expect from a fast-growing technology company, you’ll get access to a team of creative problem solvers and the chance to see your contributions make large impacts. Benefits include:
Unlimited Paid Time Off
Work from anywhere in Canada and USA
Health and Dental benefits
Up to $1,500 USD/ $2,025 CAD towards IT set up for your home
Up to 2% matching RRSP / 401K
Learning and Development opportunities
Up to $50 USD/ $67.50 CAD towards Internet/Cell phone service
Our Pledge to Fostering an Inclusive and Safe Workplace:
Wrapbook pledges to be a harassment- and discrimination-free space for everyone, regardless of age, disability, ethnicity, gender identity or expression, nationality, neurotype, personal appearance, political affiliation, professional background, race, religion, or sexual identity or orientation.
Apply Now
Have we got your attention? Submit your application today and a member of our Talent team will be in touch with you shortly!
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