Manager, Express Desk Support

Summary

Join Wrapbook as a Manager, Express Desk Support and lead a team of support specialists in resolving high-volume platform-related cases. You will manage daily operations, optimize AI-powered support, and coach your team for growth. This role requires expertise in managing technical case flows, AI systems, and support tools. You will also be responsible for hiring, onboarding, and continuous enablement of your team. The position includes leadership coverage one Sunday every three weeks. Wrapbook offers a competitive salary and benefits, including unlimited paid time off, remote work options, health and dental benefits, and learning and development opportunities.

Requirements

• 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

Responsibilities

• 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

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