Gusto is on a mission to grow the small business economy, handling payroll, health insurance, 401(k)s, and HR for more than 500,000 small businesses nationwide.
Teams in Denver, San Francisco, and New York.
All full-time employees receive competitive base pay, benefits, and equity (RSUs).
AI is a fundamental part of how work gets done; all team members are expected to actively engage with AI tools relevant to their role.
About the role
Gusto is hiring a Senior Leader to lead the Escalation Services team within Benefits Services.
This role is two jobs at once: operate a white-glove escalation service, and become the owner of Gusto's escalation ecosystem — co-creating the next iteration of how escalations are handled.
Lead a team of specialists accountable for how Gusto shows up when something has already gone wrong for a customer, while redesigning the intake, triage, tooling, and root-cause infrastructure.
The team owns executive escalations, access-to-care emergencies, and any escalation involving missing or inaccurate benefits — health insurance chief among them.
Rethink the operating model at a system level: what gets automated, what gets simplified, and what a scalable escalation ecosystem looks like as Gusto grows.
Be a senior partner in shaping how AI transforms escalation work — building the automation roadmap, coaching the team to use it, and reducing administrative overhead.
Responsibilities
Lead the specialists who run Escalation Services, running a structured cadence — weekly 1:1s, team forums, monthly business reviews.
Serve as point of contact for Gusto's highest-visibility escalations — coordinating cross-functionally to drive resolution and providing clear status updates to customer executives and internal stakeholders.
Step into the most sensitive and highest-risk cases yourself — executive-visible, compliance-related, or reputationally significant.
Coach the team to operate as drivers, not passengers — owning the case end-to-end and communicating proactively.
Own the rationale before delivering any meaningful change — running a clear playbook every time.
Run a calibrated, evidence-based performance cycle that holds a high bar, with AI fluency treated as a non-negotiable expectation.
Develop high-potential specialists through structured stretch work and direct sponsorship; address underperformance early and directly.
Redesign the end-to-end escalation operating model — intake, triage, severity tiering, and routing — so the system scales with volume and complexity.
Build and own root-cause analysis practices — turning individual escalations into trend data that identifies top drivers, systemic gaps, and opportunities to prevent recurrence upstream.
Manage dependencies across cross-functional partners.
Requirements
Senior leadership experience leading escalation or high-stakes customer service teams.
Experience redesigning operating models, intake, triage, and routing processes.
Strong root-cause analysis and trend-data practices.
Digital fluency and a proactive approach to leveraging AI tooling.
Experience coaching and developing specialists, running performance cycles.
Cross-functional coordination and stakeholder communication skills.
Conditions
Location: Denver, CO - Hybrid; Scottsdale, AZ - Hybrid.
Competitive base pay, benefits, and equity (RSUs).
Offer amounts are determined by role, level, and location.