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Gusto

Readiness Advocate, BenOps

Gusto
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hybrid senior full-time $75,000 to $110,000 per year Denver, CO

First indexed 29 May 2026

Description

About Gusto Gusto is a company that handles the hard stuff for small businesses, allowing owners to focus on their craft and customers.

Job Title: Readiness Advocate, BenOps

As a Readiness Advocate, you will turn 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.

Responsibilities

  • 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.

Requirements

  • 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

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

Salary

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.

Work Arrangement

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).

Equal Opportunity Employer

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.

This listing is enriched and indexed by YubHub. To apply, use the employer's original posting: https://job-boards.greenhouse.io/gusto/jobs/7950937