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. With teams in Denver, San Francisco, and New York, we support more than 500,000 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: 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. 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. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.