Senior Manager, CX L&D Readiness

About Gusto

At Gusto were on a mission to grow the small business economy. We handle the hard stufflike payroll health insurance 401(k)s and HRso owners can focus on their craft and customers. With teams in Denver San Francisco and New York were proud to support more than 400000 small businesses across the country and were 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. Youll 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.

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

Heres what youll 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 doesnt.

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.

Heres what were looking for:

• 7 years leading readiness enablement or L&D programs in a complex high-growth environment.
• 36 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 $140815 to $183060 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 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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