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:

• 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

• 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

• 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 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!

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