About Gusto
At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff—like payroll, health insurance, 401(k)s, and HR—so owners can focus on their craft and customers. With teams in Denver, San Francisco, and New York, we’re proud to support more than 400,000 small businesses across the country, and we’re building a workplace that represents and celebrates the customers we serve. Learn more about our Total Rewards philosophy.
About the Role:
Gusto is seeking a customer-obsessed, tactical leader for our Onboarding Advocate (OA) team. As a People Empowerer (PE), you will be a hands-on coach to a pod of Advocates, ensuring your team provides small business owners and their employees with a world-class health insurance onboarding experience.
Your primary focus is driving team performance by consistently meeting productivity and quality targets, proactively removing tactical hurdles, and coaching your team to excellence. You will play a critical role in scaling Gusto’s benefits business by ensuring our customers have a seamless transition to their new plans.
About the Team:
The Onboarding Advocate team is passionate about setting customers up for success with health benefits. We are the first point of contact after the sale and are responsible for ensuring a smooth, confident, and value-driven onboarding experience. By seamlessly managing the complexities of health benefits, we enable our customers to focus on what matters most—their people and their business. We are actively working to integrate AI tooling to enhance our processes and customer interactions, and we're excited to bring in a leader who can help accelerate this evolution.
Here’s what you’ll do day-to-day:
- Drive Operational Excellence: Manage the daily health of your team's funnel, ensuring all customer milestones and SLAs are met with urgency and accuracy.
- Empower & Coach: Provide regular coaching and performance management (via 1:1s and monthly reviews) focused on technical mastery, customer-centricity, and hitting KPIs.
- Remove Roadblocks: Act as the first point of contact for tactical blockers. You will serve as the escalation point in day-to-day execution to ensure your team never feels "stuck."
- Promote Inclusive Growth: Create a psychologically safe and inclusive environment where diverse perspectives are valued and team members feel empowered to do the best work of their lives.
- Iterate on Process: Constantly analyze team performance data to identify and solve for moments of customer pain or internal friction, refining processes to make them simpler, more efficient, and in direct service to the customer experience.
- Partner Cross-Functionally: Collaborate closely with upstream Advisory and downstream Fulfillment partners to ensure clean handoffs and a unified customer experience.
Here’s what we're looking for:
- 1-2+ years of people management experience in customer success, onboarding, renewals, or a similar customer-facing operations role.
- A true passion for coaching and developing individual contributors into high-performing, engaged team members.
- Exceptional verbal and written communication skills with the ability to deliver feedback that is both direct and supportive.
- Strong operational skills with a proactive approach to process improvement and a track record of driving process optimization efforts that improve the customer experience.
- Eager to leverage AI-powered tools to enhance team efficiency and customer outcomes, with a commitment to developing your team's AI fluency.
- Experience in the health insurance and benefits space is a strong plus. You understand the unique challenges of small business customers and have an interest in scaling processes to support higher-value segments.
Our cash compensation amount for this role is $74,285/yearly - $91,000/yearly in Denver, Phoenix, 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.
What the Team is Saying
Gusto Compensation & Benefits Highlights
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Healthcare Strength — Medical, dental, and vision coverage is described as comprehensive for employees and dependents, with mental‑health resources included. Health benefits are also available and administered within one system that syncs with payroll.
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Inclusive Benefits Coverage — Family planning and fertility support, gender‑affirming care, and a range of mental‑health resources extend coverage to diverse needs. Adoption assistance, childcare benefits, and return‑to‑work support further broaden inclusivity for different family structures.
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Leave & Time Off Breadth — Paid vacation, sick time, bereavement, holidays, and paid leaves form a wide time‑off foundation. A sabbatical program adds longer‑term rest options beyond standard PTO.
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What We Do
Gusto is a modern, online small business platform that helps small businesses take care of their teams. On top of full-service payroll, Gusto offers health insurance, 401(k)s, expert HR, and team management tools. Today, Gusto offices in Denver, San Francisco, and New York serve more than 400,000 businesses. 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.
Why Work With Us
We help small businesses—the backbone of the economy—thrive. Everything we do ladders up to empowering entrepreneurs and supporting their teams. Gusto empowers builders at every level to take initiative and make things better. You'll be solving meaningful challenges that shape the future of work.
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Employees engage in a combination of remote and on-site work.
We’ve built an inclusive, connected culture—no matter where you live. Whether near an office or remote, you’ll find opportunities to connect, grow, and belong. Employees work from the office on 2 designated days per week.
