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: The Escalations Services team is the engine that ensures our customers have peace of mind when it matters most: accessing their health insurance. We are seeking an emerging leader to guide and scale this team, delivering a best-in-class experience for thousands of small businesses and their employees. In this role, you will lead a team of 10–15 Operations Specialists (Individual Contributors) responsible for the execution and delivery of benefits administration- working directly with health insurance carriers to ensure timely and accurate coverage. This is a hands-on leadership role for the modern era. We are looking for a results-oriented owner who combines deep industry knowledge with an AI-native mindset. You will balance day-to-day tactical execution- like workflow management and carrier communications- with the strategic goal of leveraging technology to build a seamless, scalable onboarding journey. Here’s what you’ll do day-to-day: • Lead & Coach: Directly manage a team of ~15 Operations Specialists. Create an environment of continuous development through weekly 1:1s, real-time mentoring, and actionable feedback to help individuals develop their careers. • Drive Operational Execution: Ensure that benefit enrollments are processed in a timely and accurate manner within agreed-upon SLAs. Manage daily workflows to balance speed with quality. • Innovate with AI & Automation: Actively identify opportunities to leverage AI tools and automation to reduce manual administrative burden. You will coach your team on how to "work smarter" by adopting new technologies to streamline carrier interactions. • Own Performance & Metrics: Take responsibility for your team’s execution of monthly, quarterly, and annual objectives. Use scalable systems and data to monitor performance, ensuring the team meets or exceeds their goals. • Strategic Problem Solving: Serve as the primary escalation point for high-impact cases to remove roadblocks for your team, while simultaneously conducting root cause analysis to drive systemic improvements and operational efficiency. • Champion Change: Lead change management efforts by translating high-level company initiatives and OKRs into daily actions. Foster a culture of engagement where the team feels empowered to put customers first amidst a fast-paced, evolving environment. Here’s what we're looking for: • Industry Expertise (Must Have): 3+ years of experience in Benefits Administration, Health Insurance (Carrier side), or with a Benefits Broker (e.g., ADP, Rippling, Aetna, Cigna). You understand the lifecycle of a benefit order. • 3+ years of experience leading projects, mentoring peers, or serving as a Team Lead/Subject Matter Expert. • Proven track record of hiring or training top talent is a plus. • AI Fluency & Digital Agility: You embrace the "AI-native" workforce. You are comfortable using LLMs (e.g., ChatGPT, Claude, Gemini) and other modern tools to draft communications, summarize data, and solve problems faster. You don't just accept processes as they are; you look for ways to automate them. • Data-Driven Mindset: Comfortable working with data (Excel, Salesforce/SFDC, Tableau) to measure performance and make objective decisions. • Operational Agility: Experience with change management; you can inspire buy-in and keep a team organized amidst competing priorities. • Problem Solver: A creative thinker who uses a "first-principles" approach to solve complex enrollment issues while maintaining a customer-first mentality. • Education: Bachelor’s degree preferred, or equivalent relevant work experience. • Bonus Points: • Experience in a high-growth startup environment. • Specific experience with Salesforce (SFDC) reporting and dashboards. • Experience with "Prompt Engineering" or optimizing workflows using generative AI. Our cash compensation amount for this role is $86,530/yearly - $106,000/yearly in Phoenix and $92,245/yearly - $113,000/yearly in Denver, Chicago and Las Vegas. 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. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer . Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice .