Readiness Advocate, BenOps

About Gusto

At Gusto were 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 500000 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:

Youve 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. Youll coach people through live practice give honest feedback track their progress and decide when theyre ready to gousing real performance data not gut feel.

During active hiring pushes: Youre in the thick of Nestingcoaching cohorts running practice and making the call on whos ready.

During slower periods: You shift into builder modeturning your BenOps knowledge into job aids microlearning and e-learning. No instructional design background required. Well teach you everything. You bring the expertise; well give you the tools to bottle it.

What Youll Do:

• Own Nesting for your lane (OA Fulfillment or Advising)youre 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 dont clearly apply and establishes the precedent for how to handle them going forward.
• Coach new hires through live practice reverse shadowing and 1:1smeeting 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 leadershonest summaries of each new hires 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. (Well teach you how. You just need to be curious.)

What Were 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 bettercoaching 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 theyre ready to go.
• Strong written communicationyoull write docs notes and guides that others rely on.
• A builder mentality: youd rather fix the system than answer the same question 50 times.
• Genuine curiosity about instructional design and e-learning. No experience neededjust 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.

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 Gustos 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 its 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.

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