About the Role:

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.

About the Team:

Escalation Services is the last line of defense when a case has outgrown standard resolution — the point where a missed or inaccurate benefit stops being an operational miss and becomes someone's actual health coverage, prescription, or procedure. We sit at the highest-stakes intersection of Benefits Services, owning the resolution of Gusto's most complex, highest-visibility cases: executive escalations, access-to-care emergencies, and benefit inaccuracies that affect a customer's coverage.

We measure ourselves by speed, accuracy, and how the customer feels on the other end of the call — because for the people we serve, an unresolved escalation isn't an inconvenience, it's a real gap in their care. Every case that reaches this team already matters to someone; our job is to make sure it never has to escalate again.

As an AI-native company, we don't just use technology — it's the backbone of how we work. Senior leaders on this team are expected to model digital fluency and a proactive approach to leveraging AI tooling to speed resolution, surface root cause, and free up capacity for the cases that need a human touch most.

Here’s what you’ll do day-to-day:

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.

Rebuild the system

• 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.

Success looks like

• 3–6 months: The current escalation lifecycle — intake, triage, ownership, and closure — is fully audited, with a prioritized rebuild roadmap shared with leadership.
• 6–12 months: A redesigned escalation framework (tiers, ownership, playbooks) is live and adopted across Benefits Services, with a root-cause feedback loop driving measurable upstream fixes.
• 12+ months: Escalation volume and severity are measurably down, time-to-resolution has improved, and escalation health reporting is trusted by leadership as a real-time and retrospective view of the business.

Here’s what we're looking for:

Leadership experience

• 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.

Executive-level escalation management

• 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.

Operational rigor

• 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.

AI-native builder

• 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.

Coaching and development depth

• 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.

Domain-relevant experience (preferred)

• 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.

Our cash compensation range for this role is $119,185/year to $146,000/year in Denver and Phoenix. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the amounts listed above.