Senior Manager, Escalation Services

About Gusto At Gusto, we’re on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. 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. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto’s subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it’s the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. 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