Readiness Advocate, BenOps

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: You’ve spent years getting really good at BenOps work. Now imagine using that expertise to make everyone around you better at it too. The Readiness Advocate turns brand-new hires into confident, capable BenOps teammates. You’ll coach people through live practice, give honest feedback, track their progress, and decide when they’re ready to go—using real performance data, not gut feel. During active hiring pushes: You’re in the thick of Nesting—coaching cohorts, running practice, and making the call on who’s ready. During slower periods: You shift into builder mode—turning your BenOps knowledge into job aids, microlearning, and e-learning. No instructional design background required. We’ll teach you everything. You bring the expertise; we’ll give you the tools to bottle it. What You'll Do: Own Nesting for your lane (OA, Fulfillment or Advising)—you’re the expert in the room, and new hires will count on you to show them what “good” looks like. Serves as the functional authority for OA, Fulfillment or Advising readiness standards within the Readiness team. Assesses edge cases and non-standard learner situations where established criteria don't clearly apply, and establishes the precedent for how to handle them going forward. Coach new hires through live practice, reverse shadowing, and 1:1s—meeting people where they are and helping them grow fast. Build the tools your lane runs on: run-of-show docs, facilitator guides, rubrics, and readiness criteria that keep the experience consistent and fair. Use quality scores, adherence, and throughput data to make clear, evidence-based readiness calls. Write handoff notes that actually help permanent leaders—honest summaries of each new hire’s strengths, risks, and next steps. Designs readiness approaches for new BenOps roles or workflows where no prior Nesting model exists. Develops evaluation criteria when performance signals are ambiguous or the role is new to the Readiness program. Partners with BenOps and CX L&D leadership to shape readiness criteria and advocate for changes to the ramp model. Advises BenOps leaders on readiness trends, systemic training gaps, and recommended program adjustments. During slower periods, build e-learning, microlearning, and in-the-flow job aids that make BenOps better long-term. (We’ll teach you how. You just need to be curious.) What We're Looking For: 5+ years in BenOps, L&D, or a related operational training function — or equivalent demonstrated expertise Deep expertise in OA, Advising, or Fulfillment. A track record of helping others get better—coaching, mentoring, or training in any context. The ability to give honest, clear feedback without making people feel bad about themselves. Good judgment about when someone needs more support versus when they’re ready to go. Strong written communication—you’ll write docs, notes, and guides that others rely on. A builder mentality: you’d rather fix the system than answer the same question 50 times. Genuine curiosity about instructional design and e-learning. No experience needed—just an open mind. We will train you. Nice to Have: Experience in a coaching, facilitation, or onboarding role. Familiarity with BenOps tools like Salesforce, Hippo, NBA, or telephony. Experience building content in slides, docs, LMS platforms, or knowledge bases. Our cash compensation amount for this role is $75,000/yr to $90,000/yr in Denver & most major metro locations, and $91,000/yr to $110,000/yr for San Francisco & New York. 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. 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