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  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.

You’ve spent years getting really good at Ben Ops 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 Ben Ops 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.

You’re in the thick of Nesting—coaching cohorts, running practice, and making the call on who’s ready.

You shift into builder mode—turning your Ben Ops 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.

• 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.
• Assess edge cases and non-standard learner situations where established criteria don't clearly apply, and establish 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.
• Design readiness approaches for new Ben Ops roles or workflows where no prior Nesting model exists.
• Develop evaluation criteria when performance signals are ambiguous or the role is new to the Readiness program.
• Partner with Ben Ops and CX L&D leadership to shape readiness criteria and advocate for changes to the ramp model.
• Advise Ben Ops 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 Ben Ops better long-term. (We’ll teach you how. You just need to be curious.)

• 5+ years in Ben Ops, 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.

• Experience in a coaching, facilitation, or onboarding role.
• Familiarity with Ben Ops tools like Salesforce, Hippo, NBA, or telephony.
• Experience building content in slides, docs, LMS…