[Hiring] Senior Product Manager II @Wrapbook

Role Description

Do you love the hardest kind of product problem, where the data model is the product and a good decision compounds across everything downstream of it? Are you a self-starter who thrives on technical depth, systems thinking, and real customer stakes? Then this role is for you.

We're looking for an experienced Senior Product Manager to own the Agreement Data Platform at the core of Wrapbook's payroll engine. This team owns the union agreements, signatories, job classifications, wage tables, scale rates, and the agreement rules that set the pay floor, and the relationships between them, that every payroll calculation on Wrapbook depends on.

Just as importantly, it owns the operator tooling that lets our contract administrators and client operations partners define, configure, and govern that data without engineering in the critical path.

This is one of the highest-leverage roles in the product org. Agreement data is the spine of the payroll product: every downstream decision, from rate selection on hire, to pay-rule application on a timecard, to the contributions and reports customers receive, is conditioned on its shape. Your mandate is to make this data accurate, configurable, governable, and legible, and to do it in a way that scales as the number of agreements, signatories, and productions grows.

You'll partner with a tenured engineering team and be a key product voice at the crossroads of nearly every payroll team at Wrapbook.

What You'll Do:

• Own the roadmap and vision for the Agreement Data Platform, aligning customer and operator needs with company priorities.
• Treat the data model as the product. Define new entities, attributes, and relationships as the industry negotiates new terms and new agreement types come under scope, and decide what is universal versus agreement-specific.
• Drive the operator-led bet. Invest in admin tooling, validation, and self-service primitives so a Contract Administrator can stand up and maintain an agreement end-to-end without an engineering ticket.
• Steward legible interfaces. The platform's data is a dependency for every payroll team, so you'll define explicit contracts (APIs, data services) and surface model changes early so other teams can build on your work without surprises.
• Partner closely with engineering on high-stakes work: the migration off the legacy job-classification model, the Lookup Service extraction, and rule explainability, where correctness has real financial and legal consequences.
• Collaborate cross-functionally with the teams upstream and downstream of you, worker hiring and onboarding, project setup, payroll calculations, contributions, timecards, reporting, client operations, and labor relations, to keep boundaries clear and dependencies predictable.
• Define success metrics and use data-driven insight to prioritize and measure impact.
• Advocate for accuracy, compliance, and traceability. When a paymaster asks "why did this calculate this way?", the answer should be in the tool, not a Slack thread.
• Drive execution end-to-end, from discovery through launch, with predictable delivery.
• Use AI tools daily to accelerate your workflow, from discovery and analysis to writing, code comprehension, and prototyping. We expect our PMs to be builders, not just strategists.

Qualifications

• 5+ years of product management experience in a SaaS, fintech, or similarly complex technical environment, with meaningful time owning platform, infrastructure, or data-platform products.
• A strong technical orientation. You reason with engineering about data models, service boundaries, integrations, and data flows without heavy hand-holding.
• Proven ability to define and execute product strategy with measurable outcomes, and to independently take an idea from concept to launch.
• You are an active, daily user of AI tools to do your job.
• Experience owning products with high cross-team surface area, where other teams depend on the systems or data you own.
• Excellent written communication. Clear, structured, decision-oriented specs and data contracts that engineering can build from without ambiguity.
• Strong analytical and problem-solving skills, comfort with ambiguity, and the ability to become a subject-matter expert in a complex domain quickly.
• Ability to independently leverage data using tools like SQL, Pendo, Omni, or Snowflake to uncover insights and inform decisions.
• Bias toward action, balanced with the attention to compliance and quality that a payroll platform demands.

Extra Points if You Have:

• Domain Expertise: payroll, fintech, or entertainment industry experience, especially with complex compliance or regulatory requirements.
• Platform / Data-Layer Experience: you've owned a data model, rules engine, configuration platform, or internal-tooling-for-operators product that other teams built on top of.
• Operator Tooling Experience: you've built admin panels or self-serve configuration surfaces that moved work out of engineering and into the hands of operations teams.
• Modularization / Service Boundaries: you've helped extract a service or draw an enforced interface boundary inside a large codebase.
• AI Builder, Not Just User: beyond using AI tools, you've built prototypes, internal tools, or workflows using LLMs, MCPs, or AI-assisted development tools.

Benefits

• 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

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