Senior Manager, Escalation Services

Gusto•Denver, AZ

1d•$119,185 - $146,000•Hybrid

About The Position

Gusto is hiring a Senior Leader to lead our 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, not just managing the team that handles them today. You'll lead a team of specialists, accountable for how Gusto shows up today when something has already gone wrong for a customer — while simultaneously redesigning the intake, triage, tooling, and root-cause infrastructure that determines how well Escalation Services performs a year from now. Your team owns comprehensive, white-glove escalation management: executive escalations, access-to-care emergencies, and any internally or externally sourced escalation involving missing or inaccurate benefits — health insurance chief among them. When a member can't fill a prescription, an employee loses active coverage, or a customer executive needs a direct answer, your team is the one that steps in, resolves it, and closes the loop. The other half is the build. This function's current operating model — how escalations get triaged, routed, resolved, and learned from — wasn't designed for the volume and complexity it now handles. You're being hired to rethink it at a system level — what gets automated, what gets simplified, and what a scalable escalation ecosystem looks like as Gusto grows. Your impact will be measured in leverage: how much escalation volume the system can absorb without depending on individual heroics, and how clearly escalation health becomes a trusted, leading indicator for leadership. You'll also be a senior partner in shaping how AI transforms escalation work at Gusto — building the automation roadmap, coaching your team to use it, and reducing the administrative overhead that keeps specialists from spending time where it matters most: with the customer.

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, or scaling — and bringing teams along through it.
A track record of doing both at once: running a team's day-to-day performance while simultaneously redesigning the process or system it operates on. This is not a “stabilize first, then improve” role — you'll need to hold both threads at the same time without dropping either.
Proven ability to manage high-pressure, high-visibility escalations and communicate clearly across a broad range of audiences — from frontline specialists to customer executives and internal SLT.
Track record of building bridges across Product, Engineering, and Legal to drive root-cause fixes, not just case-by-case resolution.
Insatiable curiosity and an unrelenting drive to ask why — you get to root cause and don't stop at the symptom.
Comfortable reading dashboards, interrogating data, and finding the gap before it shows up as an escalation.
Track record of operating against time-sensitive SLAs in a benefits, healthcare, payroll, banking, insurance, or comparable regulated operations environment.
Experience building balanced scorecards and operational reporting that surfaces the right KPIs for regular 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, and you can point to the leverage it created.
You coach AI fluency in others and evaluate new tools with judgment — you can tell the difference between a demo that's impressive and a tool that will actually move the needle in escalation resolution.
Systems thinker: you look for root causes at the process level, not just the case level, and build solutions that scale past your own bandwidth.
You develop your specialists through structured coaching, not directives. Team members leave your 1:1s with a clearer picture of the bar, not just your opinions.
You hold the bar on performance with care — you have hard conversations early, address underperformance directly, and don't let the bar drift to preserve a relationship.

Nice To Haves

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 the leadership and AI fluency are there.

Responsibilities

Operate a white-glove escalation service
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, confident status updates to customer executives and internal stakeholders alike.
Step into the most sensitive and highest-risk cases yourself — executive-visible, compliance-related, or reputationally significant — working them alongside your team, not just above it.
Coach your team to operate as drivers, not passengers — owning the case end-to-end, communicating proactively, and holding the bar on white-glove service without waiting to be told what “good” looks like.
Own the rationale before you deliver any meaningful change — running a clear playbook every time: what's changing, why, what it means for the team, what resources are in place, how it gets owned.
Run a calibrated, evidence-based performance cycle that holds a high bar across your team, 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, with the same care and clarity you bring to recognition.
Redesign the end-to-end escalation operating model — intake, triage, severity tiering, and routing — so the system scales with volume and complexity instead of depending on individual heroics.
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, leveraged teams, and carrier partners — persuading and aligning to drive fixes at the source, not just the symptom.
Define and socialize an escalation policy for Benefits Services — what qualifies as an escalation, who owns what, and what “resolved” means — so the system is legible outside the team, not just inside it.
Establish and own the KPIs, dashboards, and reporting that make escalation trends visible to leadership — time-to-resolution, reopen rate, CSAT/NPS on escalated cases, and SLA/SLO adherence.
Set the AI vision and own the automation roadmap for Escalation Services — identifying where AI can accelerate triage, surface root cause, and reduce manual case handling, and partnering with Data, Engineering, and Product to build it.