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Salary: USD 119,185 - 146,000 / annual
Gusto is hiring a Senior Manager to lead the Escalation Services team within Benefits Services. This is a dual-mandate role: operate a white-glove escalation service handling Gusto's most complex, highest-visibility cases (executive escalations, access-to-care emergencies, and benefit inaccuracies affecting customer coverage), while simultaneously redesigning the escalation ecosystem—intake, triage, tooling, and root-cause infrastructure—to scale with volume and complexity.
Day-to-day responsibilities include leading a team of specialists through structured cadences (weekly 1:1s, team forums, monthly business reviews); serving as point of contact for highest-visibility escalations and coordinating cross-functionally to drive resolution; stepping into the most sensitive and highest-risk cases yourself; coaching your team to operate as drivers, not passengers; and running a calibrated, evidence-based performance cycle with AI fluency as a non-negotiable expectation.
The rebuild work involves redesigning the end-to-end escalation operating model so the system scales without depending on individual heroics; building and owning root-cause analysis practices to turn individual escalations into trend data; managing dependencies across cross-functional partners and carrier partners to drive fixes at the source; defining and socializing escalation policy for Benefits Services; establishing KPIs, dashboards, and reporting that make escalation trends visible to leadership; and setting the AI vision and owning the automation roadmap for Escalation Services.
Success milestones: 3–6 months, the current escalation lifecycle is fully audited with a prioritized rebuild roadmap; 6–12 months, a redesigned escalation framework is live and adopted across Benefits Services with a root-cause feedback loop driving upstream fixes; 12+ months, escalation volume and severity are measurably down, time-to-resolution has improved, and escalation health reporting is trusted by leadership.
Gusto is a payroll, benefits, and HR platform serving 500,000+ small businesses. The company operates offices in Denver, San Francisco, and New York, with hybrid expectations of 2–3 days per week in office. All full-time employees receive competitive base pay, benefits, and equity (RSUs).
REQUIREMENTS:
- 5+ years of leadership experience, including 2+ years leading other leaders (preferred)
- Demonstrated track record of owning escalation, technical support, or supportability functions in a fast-paced, customer-obsessed environment
- Experience driving org change (restructures, process redesign, scaling) and bringing teams along through it
- Proven ability to manage high-pressure, high-visibility escalations and communicate clearly across frontline specialists, customer executives, and internal SLT
- Track record of building bridges across Product, Engineering, and Legal to drive root-cause fixes
- Insatiable curiosity and unrelenting drive to ask why; you get to root cause and don't stop at the symptom
- Comfortable reading dashboards, interrogating data, and finding gaps before they become escalations
- Track record of operating against time-sensitive SLAs in benefits, healthcare, payroll, banking, insurance, or comparable regulated operations environment
- Experience building balanced scorecards and operational reporting that surfaces the right KPIs for leadership review
- You don't just use AI tools—you build with them. You've personally designed or automated a workflow, built an agent, or stood up a process that meaningfully changed how a team operates
- You coach AI fluency in others and evaluate new tools with judgment
- Systems thinker: you look for root causes at the process level and build solutions that scale past your own bandwidth
- You develop specialists through structured coaching, not directives
- You hold the bar on performance with care—you have hard conversations early and address underperformance directly
- Domain-relevant experience in benefits operations, health insurance brokerage, employee benefits administration, access-to-care advocacy, or payroll is a strong plus
- Experience with carrier portals, Salesforce, and high-volume case management tooling is helpful but not required if leadership and AI fluency are strong
