Customer Success AI and Automation Lead
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:
Capacity Creation
Conduct structured time and workflow audits across Success and Support
Identify high-impact, repeatable manual workflows
Map processes end-to-end including inputs, decisions, and exceptions
Design and launch AI-assisted workflows used consistently by CSMs
Quantify and validate annualized hours saved
Ensure reclaimed time translates into proactive engagement, not reactive drift
Signal Discovery & Prioritization
Identify 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
Workflow Automation
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
Adoption & Enablement
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 be a software engineer, but you must be technically fluent and capable of executing on automation design in partnership with technical teammates. 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!
#LI-Remote