Senior Leader, Escalation Services & AI Transformation

Monograph; Scottsdale (AZ); Hybrid; USD 119,000 - 146,000; Full time

Job summary

Gusto is seeking a Senior Leader to head the Escalation Services team within Benefits Services. You’ll manage a white-glove escalation program for high-visibility cases and redesign the escalation ecosystem for scale, automation, and better outcomes for customers.

You'll partner with cross-functional groups (Product, Engineering, Legal, Data) to define playbooks, implement AI-enabled triage, and set KPIs that drive faster resolutions while maintaining service excellence.

Qualifications

• 5+ years of leadership experience, including leading other leaders.
• Experience owning escalation, technical support, or supportability functions in a fast-paced, customer-obsessed environment.
• Experience driving organization changes — restructures or process redesign.

Responsibilities

• Operate a white-glove escalation service with a structured cadence and cross-functional coordination.
• Redesign the end-to-end escalation operating model to scale with volume and complexity.
• Own KPIs, dashboards, and reporting to inform leadership on escalation trends.
• Define an AI roadmap for Escalation Services and partner with Product, Data, and Engineering.
• Coach and develop specialists through structured coaching and performance management.

Skills

Leadership experience

Escalation management

AI tooling fluency

Tools

Salesforce

Carrier portals

Job description

Gusto is seeking a Senior Leader to head the Escalation Services team within Benefits Services. You’ll manage a white-glove escalation program for high-visibility cases and redesign the escalation ecosystem for scale, automation, and better outcomes for customers.

You'll partner with cross-functional groups (Product, Engineering, Legal, Data) to define playbooks, implement AI-enabled triage, and set KPIs that drive faster resolutions while maintaining service excellence.