Head of Escalation Services & AI-Driven Resolution

The Wrap; Denver (CO); Hybrid; USD 119,000 - 146,000; Full time

Benefits offered by this job

Equity (RSUs)

Job summary

Gusto is hiring a Senior Leader to head Escalation Services within Benefits Services. You will own a white-glove escalation program and the escalation ecosystem, redesigning intake, triage, tooling, and root-cause infrastructure for scalable performance.

You’ll lead specialists handling executive escalations, access-to-care emergencies, and benefit inaccuracies, while shaping AI-driven automation and rapid resolution strategies across the organization.

Qualifications

• 5+ years of leadership experience, including 2+ years leading other leaders.
• Experience owning escalation, technical support, or supportability in fast-paced environments.
• Experience driving org change — restructures, process redesign, or scaling teams.
• AI fluency and ability to leverage AI tooling to speed resolution.

Responsibilities

• Operate a white-glove escalation service with a structured cadence.
• Serve as the point of contact for high-visibility escalations and coordinate cross-functional teams.
• Redesign escalation operating model to scale with volume and complexity.
• Define and socialize an escalation policy for Benefits Services.

Skills

Leadership experience

AI fluency

Escalation management

Cross-functional collaboration

Coaching people

Tools

Salesforce

Carrier portals

Job description

Gusto is hiring a Senior Leader to head Escalation Services within Benefits Services. You will own a white-glove escalation program and the escalation ecosystem, redesigning intake, triage, tooling, and root-cause infrastructure for scalable performance.

You’ll lead specialists handling executive escalations, access-to-care emergencies, and benefit inaccuracies, while shaping AI-driven automation and rapid resolution strategies across the organization.