Senior Manager, CX L&D Readiness

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:

The Senior Manager, CX L&D Readiness is the architect of an AI-powered readiness ecosystem across all CX teams — including Customer Care, Benefits Operations, and Payroll Operations. You’ll redefine how Gusto delivers readiness, integrating automation, adaptive learning, and data-driven coaching to accelerate time-to-proficiency, strengthen QA outcomes, and scale performance support across thousands of advocates.

You’ll architect Gusto’s AI-Native Readiness strategy defining how GenAI, adaptive simulations, and predictive learning agents reshape skill development and performance support. You’ll apply principles of data integrity, feedback loops, and Responsible AI to ensure learning at scale is both personalized and ethical.

Here’s what you’ll do day-to-day:

Advocate & Customer Experience

• Own readiness end-to-end, ensuring advocates are confident and competent as they transition from onboarding to production.
• Extend readiness into ongoing upskilling and reskilling, helping teams adapt as products, skills, and AI tools evolve.
• Partner with QA, WFM, and CX Operations to align readiness with performance metrics like QA scores, first-contact resolution, and handle time.
• Deploy AI-assisted coaching flows that identify learning gaps and surface “next best actions” for advocates and managers.
• Collaborate with Voice of the Customer and Process Improvement teams to identify friction points and build AI-informed interventions that improve both Gustie and Gustomer experiences.

Learning Strategy & Execution:

• Design adaptive readiness journeys powered by AI adjusting practice sets, simulations, and job aids in real time based on performance data.
• Use predictive analytics and readiness dashboards to anticipate risk, target interventions, and optimize ramp time.
• Automate the content workflow: leverage AI to draft, version, and QA readiness materials, freeing designers and facilitators for high-impact work.
• Partner with L&D peers to create an AI-ready content structure (modular, tagged, and retrievable) that powers learning in the flow of work.
• Create evaluation plans for AI features that include accuracy checks, bias and safety reviews, and business impact metrics.
• Standardize readiness playbooks, curricula, and QA checkpoints across CX.
• Leverage AI agents and adaptive learning to deliver just-in-time support, personalized readiness interventions, and data-driven insights at scale.
• Own the experimentation pipeline for new AI-powered readiness features, using A/B testing and rapid iteration to measure improvements in time-to-proficiency (TTP) and QA performance.
• Establish standardized prompt design and retrieval practices to ensure high-quality, bias-mitigated outputs across readiness agents.

Team Empowerment:

• Lead, coach, and develop a team of Readiness leaders (PEs) to operate as AI-native enablement professionals.
• Foster experimentation with AI tools from prompt-driven design to workflow automation anchored in data accuracy, ethical use, and business value.
• Build career paths and skill development opportunities within the team.
• Build psychological safety for innovation, encouraging iteration and visible learning around what works and what doesn’t.

Cross-L&D Collaboration:

• Partner with Instructional Design on aligning readiness content with curricula and create AI-ready content structures that improve retrieval quality.
• Partner with Facilitation & Programs to ensure a seamless hand-off between onboarding and readiness.
• Partner with Learning Strategy & Ops to measure readiness impact, build dashboards and review cadences that separate vanity metrics from true proficiency gains to inform CXLT-level decisions.
• Partner with Product and Engineering to support the adoption and continuous improvement of AI tools for customer facing employees.
• Share best practices and insights across the broader Gusto L&D community.

AI and Automation:

• Treat AI as an amplifier of human enablement, not a replacement for it.
• Drive the roadmap for AI-powered delivery, QA augmentation, and learning automation from scoping pilots to scaling successful use cases.
• Establish rigorous evaluation criteria for AI use: accuracy, bias, safety, latency, and relevance.
• Partner with Security, Legal, and People Tech to ensure compliance and responsible data handling.
• Define metrics that prove business value faster ramp, reduced QA fallout, improved readiness survey scores, and higher retention.
• Implement and govern Responsible AI frameworks for readiness agents, including bias detection, accuracy audits, and opt-out pathways.

Here’s what we're looking for:

• 7+ years leading readiness, enablement, or L&D programs in a complex, high-growth environment.
• 3–6 years managing operations, technology, or enablement teams.
• Demonstrated success scaling AI-powered learning or workflow automation with measurable impact.
• Strong grounding in learning science, coaching, and adult development.
• Proven ability to connect learning initiatives to operational outcomes (QA, retention, ramp time, deflection).
• Expertise in using or managing AI tools for content generation, data synthesis, QA support, or adaptive learning.
• High data literacy and comfort building dashboards or working with readiness analytics.
• Ability to translate ambiguous opportunities into experiments with clear success criteria.
• Exceptional communication and stakeholder management across technical and non-technical partners.
• Familiarity with LLMs (e.g., GPT-based systems) and their applications in learning or operational workflows.
• Experience defining or applying Responsible AI frameworks — accuracy, bias, latency, and safety reviews.
• Comfort leading through change with clarity, empathy, and strategic focus.
• Travel to our Customer Experience Hubs and vendor sites (Denver, Las Vegas, Phoenix, Chicago, Manila, Guatemala City) is expected ~30% annually, increasing to 50% during peak hiring or program launches.

Our cash compensation range for this role is $140,815 to $183,060 in Denver, Chicago & Phoenix. Final offer amounts are determined by multiple factors, including candidate location, experience and expertise, and may vary from the level and 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.

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