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 - Customer Success AI and Automation Lead (Remote - USA / Canada)
We are seeking a systems-minded AI Systems Manager to help evolve Client Success and Support through AI-enabled workflow redesign, structured experimentation, and measurable capacity creation.
You will report to the Director of AI & Operational Transformation and partner closely with Customer Success and Support leadership. This is a hands-on execution role that combines process mapping, experimentation, automation design, and cross-functional influence.
What You'll Do:
Design Intelligent Workflows That Reclaim CapacityIdentify high-friction, high-volume manual work across Success and Support
Design and deploy AI-assisted workflows that eliminate repetitive tasks
Build CSM copilots that automate summaries, prioritization, and follow-ups
Replace reactive triage with intelligent signal-driven engagement
Continuously iterate workflows based on real-world usage and impact
In service to quantifying reclaimed capacity and ensuring time shifts toward proactive revenue-generating/protecting work
Signal Discovery & PrioritizationIdentify leading indicators in a consumption-based model (usage patterns, friction events, anomalies)
Run structured micro-pilots to validate signal usefulness
Track false positives, investigation cost, and intervention outcomes
Evolve validated signals into a practical prioritization model
Ensure signals drive clear CSM action, not dashboards
Translate mapped workflows into AI-ready playbooks
Build and deploy automations directly using Salesforce Flow, Zapier, Airia, Pendo, or similar platforms
Start with small, high-leverage automation slices before expanding scope
Iterate based on usage and feedback
Partner directly with frontline CSMs and Support teams
Drive weekly usage of deployed workflows
Gather feedback and continuously improve
Document learnings to enable replication across other functions
What Success Looks Like
Measurable annualized capacity creation across Success and Support
Clear shift in CSM time allocation from reactive to proactive work
Validated leading signals that improve prioritization
A documented, reusable playbook for broader rollout
What You'll Have
You are a pragmatic systems thinker who enjoys redesigning how work gets done. You likely have experience in Customer Success Operations, Business Operations or RevOps, process improvement or automation, AI-enabled workflow design, or product or program management in operational environments. This role requires someone who can bridge strategic thinking with hands-on execution.
You are also comfortable mapping workflows in detail, running structured experiments, and measuring operational ROI. You collaborate effectively with engineers, influence frontline teams, and communicate clearly across both technical and non-technical stakeholders.
You do not need to have a software engineering background, but you must be technically fluent. This includes working with LLM APIs (e.g., OpenAI or similar), iterating on prompts, and building or orchestrating agent-based workflows in addition to working with tools like SFDC, Zapier, Pendo, and Iterable.
You should have familiarity with emerging AI tooling and strong curiosity to evaluate and experiment quickly. This is not a back-office builder role: it requires strong communication, cross-functional partnership, and the ability to drive adoption.
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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What We Do
Employers in media production and the entertainment industry are constantly hiring. Freelance employees move between projects and could get onboarded 30 or more times in a single year. And yet, much of the industry uses physical paperwork with no easy way to track payments, often struggling with compliance (due to ever-changing laws and union rules), and has few automation processes in place when it comes time to send payroll reports to their accountants. Wrapbook is an intuitive payroll and insurance solution for those balancing multiple projects. With digital solutions, simplified compliance, and comprehensive reporting, we take the stress away so employers and project-based workers can focus on the big picture. Commercial producers, filmmakers, and anyone creating media deserve robust solutions to meet their unique demands. With Wrapbook, you only have to ask for documents from cast and crew once. Our platform lets you move all the onboarding forms associated with any crew from a project to any future ones, giving you back hours. By swapping out paper timecards with digital ones, approving payroll is now a piece of cake. Crew can log into Wrapbook from any device to enter their hours and expenses. Providing producers with the right tools to onboard crew and process payments helps them put routine work on auto-pilot. That way, they can focus on more compelling tasks. Let us tackle paperwork, payroll, and insurance, so you can continue creating the work that matters.
