CX Learning & Development Facilitation & Programs Manager

Gusto • Denver, CO;New York, NY;San Francisco, CA; Phoenix, AZ • 15h ago

Why This Job is Featured on The SaaS Jobs

Customer Experience organisations in SaaS increasingly rely on structured enablement to keep service quality consistent as products, customer segments, and support motions evolve. This role sits at that intersection, shaping how a CX workforce learns across onboarding, upskilling, and leadership development, with an emphasis on cohort delivery and measurable outcomes rather than ad hoc training.

For a SaaS career, the value is in building repeatable learning systems that scale with headcount and changing product complexity. Managing facilitators while owning end to end programs develops a blend of operational discipline, instructional craft, and stakeholder influence that transfers across SaaS functions, from revenue enablement to customer education. The remit also signals growing demand for AI enabled workflows in internal enablement, giving relevant exposure to how modern SaaS teams accelerate content creation, analysis, and program iteration.

This position tends to suit a practitioner ready to move from individual facilitation into leading a facilitation function, with comfort balancing delivery quality and program governance. It will appeal to professionals who prefer data informed iteration, cross functional partnership, and hands on involvement across in person and virtual learning environments.

The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.

Job Description

About the Role:

Our CX Learning & Development team is shaping the future of how our teams learn and grow at Gusto. We're hiring a dynamic Learning & Development Manager to lead our team of facilitators and oversee the delivery and continuous improvement of high-impact learning programs. This role will focus on people management, facilitation strategy, cohort experiences, and program delivery to ensure every learning moment is engaging, effective, and inclusive.

About the Team:

This role is part of our Learning & Development team, within our Customer Experience organization. Our CX organization is the linchpin of our world-class experience. With their passion, insight, and customer advocacy, the CX team has helped Gusto maintain industry-leading NPS scores while serving over 500,000 customers. We strive to positively influence millions of businesses and hundreds of millions of employees across the county.

Here’s what you’ll do day-to-day:

People Empowerment
- - Manage and develop team members, providing regular coaching, feedback, and development opportunities to help them achieve their professional goals and deliver high performance.
  - Foster a culture of growth, collaboration, and inclusivity, ensuring team members feel supported and empowered to excel in their roles.
  - Conduct performance reviews, set clear expectations, and create individualized development plans that align with team and organizational goals.
  - Act as a mentor and role model, cultivating leadership skills in team members and ensuring alignment with Gusto’s People Empowerer (PE) philosophy.
Facilitation & Design
- - Oversee facilitation strategy and program execution across multiple L&D offerings, including onboarding, upskilling & leadership development.
  - Drive quality, consistency, and scalability of cohort-based learning experiences.
  - Ensure facilitation methods align with Gusto’s values, program objectives, and audience needs.
  - Support in person, virtual, and hybrid facilitation efforts as needed, delivering impactful training sessions that align with program goals and learner needs.
  - Partner with the instructional design team to ensure high-quality, engaging course content that meets the needs of learners and the business.
  - Assist in crafting and managing communications for learning initiatives, ensuring clarity and alignment across programs.
Program Management
- - Own multiple high-impact L&D programs, overseeing their end-to-end implementation, effectiveness, and continuous improvement.
  - Ensure program milestones, deliverables, and timelines are met while maintaining alignment with Gusto’s business objectives.
  - Collaborate with the team to refine program designs based on learner feedback, data insights, and evolving organizational priorities.
  - Drive operational efficiency by identifying and addressing challenges within program workflows, ensuring seamless execution and impact.
Stakeholder Partnership
- - Act as a trusted advisor to key business stakeholders regarding facilitator effectiveness and learner outcomes.
  - Represent the facilitation function in strategic planning and retro discussions
  - Build and maintain strong relationships with cross-functional stakeholders, serving as a trusted partner to align L&D initiatives with broader business goals.
  - Represent the L&D team in strategic discussions with leadership, advocating for resources and influencing decisions to support team and organizational priorities.
  - Act as a primary contact for senior stakeholders, gathering feedback, addressing concerns, and ensuring programs drive measurable business impact.
Continuous Improvement
- - Leverage feedback, data, and learner insights to improve program experiences.
  - Create a culture of reflection and experimentation within the facilitation team.
  - Support knowledge sharing and documentation across programs.
  - Contribute to annual planning cycles, ensuring the team’s work supports broader organizational strategies and goals.

Here’s what we're looking for:

5+ years L&D experience with emphasis on facilitation and program management
Demonstrated leadership within the learning and development space
Skilled facilitator and presenter with passion for learner engagement
Experienced in managing complex, cohort-based learning programs at scale
Strong stakeholder management, relationship-building, and influence skills
Data-informed decision-maker with expertise in performance metrics
Effective communicator and collaborator across teams and levels
Flexible contributor, able to support all aspects of the L&D lifecycle
Willing to travel up to 50%
A passion for fostering a positive, inclusive, and growth-oriented team culture.
AI-fluent in practice, not just in theory; you use AI tools consistently in your day-to-day workflow to accelerate copy, program design, and analysis, and you're building toward systematizing those habits for your team.
Demonstrated experience designing, implementing, and evaluating AI-enabled learning solutions.
Demonstrated experimentation with AI applications in learning, communication, or content design.
Technical and AI-related skills:
- Practical experience with modern AI tools and workflows used in L&D. Familiarity with LLMs, prompt engineering, and APIs/integrations.
- Familiarity with AI tools that support content creation, data analysis, or learner engagement.
- Ability to prompt and fine-tune AI tools to produce high-quality, relevant, and brand-aligned outputs.
- Skilled in balancing automation with human creativity, ensuring learning experiences remain empathetic and human-centered.

The cash compensation range for this role is $138,365 - $169,000 in New York, NY & San Francisco, CA and $106,940 - $139,500 in Denver, CO and Phoenix, AZ. Final offer amounts are determined by multiple factors including candidate location, experience, and expertise.

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