Manager, Express Desk Support

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 - Manager, Express Desk Support - (Remote - USA / CANADA)

We’re looking for a Manager, Express Desk Support to lead a team of frontline support specialists focused on resolving high-volume, platform-related cases with speed, accuracy, and empathy. This role combines daily team management with ownership of our AI-powered support experience. You’ll play a key role in coaching your team, optimizing performance, and improving automation workflows in partnership with our product and engineering teams. The ideal candidate is a strong operator who thrives on team development, loves solving process problems, and gets excited about how AI can level up human support.

Note: This role includes leadership coverage one Sunday every three weeks as part of the regular schedule.

What You’ll Do:

• Lead and support a specialized Support team focused on high-volume case resolution from Worker type users, bug escalation, and AI-assisted workflows.

• Own and optimize our Decagon AI integration, including writing and maintaining AI Agent Operating Procedures (AOPs) that drive accurate, consistent, and scalable automated responses via AI Chat and AI Email.

• Manage daily operations, including scheduling, workload distribution, quality assurance, and performance monitoring.

• Serve as the first point of escalation for complex or sensitive cases, applying expert-level knowledge to unblock issues and guide resolution.

• Deliver regular 1:1s, career plans, performance reviews, and real-time coaching to drive IC growth, engagement, and performance.

• Own hiring, onboarding, and continuous enablement to ensure your team is equipped and empowered to succeed.

• Lead a QA function for AI-assisted interactions, overseeing reviews, annotations, and iterative improvements to automated replies.

• Collaborate cross-functionally with Product, Engineering, and other support teams to enhance bug handling, automation logic, and intent recognition.

• Champion AI literacy within the team, ensuring frontline agents understand how to work effectively alongside automation.

• Stay current with emerging AI capabilities and recommend enhancements to support workflows and tooling.

• Analyze deflection performance and user feedback to identify trends, gaps, and areas for continuous improvement.

• Monitor and report on team OKRs and support metrics; drive improvements to documentation, tools, and internal processes.

• Foster a healthy, inclusive team culture grounded in psychological safety, trust, and continuous feedback.

• Be available to work one Sunday every three weeks, providing leadership coverage during weekend Express Desk hours.

What You’ll Have:

• 4+ years of experience in customer support, with 1+ years managing people directly.

• Proven ability to lead high-performing support teams in fast-paced, high-volume environments.

• Experience supporting or managing technical case flows, ideally within SaaS or operations-heavy products, and AI systems.

• Strong decision-making skills and comfort working independently to resolve issues and optimize performance.

• Familiarity with support tools like Salesforce (SFDC), Jira, Decagon, or equivalent systems.

• A passion for developing people and building inclusive, trust-based team environments.

• Excellent written and verbal communication skills—you’re clear, compassionate, and calm under pressure.

• Strong organizational and prioritization skills, with the ability to manage both immediate case needs and long-term improvements.

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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