CX Learning & Development Facilitation & Programs Manager

About Gusto At Gusto, we're 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.

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.

Key Responsibilities

• 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.

Requirements

• 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.