Senior Learning and Development Specialist

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. 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 dedicated to building an exceptional customer experience by equipping our CX professionals with the skills they need to thrive, and it all starts with creating impactful, data-driven learning experiences. We are seeking a highly skilled and motivated Senior Learning & Development Specialist to lead program design, facilitate learning in key areas, and manage stakeholder relationships to drive business success. The ideal candidate will have experience in robust course design, program management, and coaching, with a track record of delivering high-quality learning solutions in fast-paced environments. 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 country. Here’s What You’ll Do Day-to-day Facilitation Facilitate in-person, virtual, and hybrid learning sessions across at least six distinct and complex knowledge areas, demonstrating a deep understanding of subject matter and the ability to tailor delivery for various audience levels, including mid & senior leadership participants. Take the lead in creating an inclusive and dynamic learning environment that challenges participants to apply critical thinking and problem-solving skills in real-world scenarios. Actively engage learners through interactive techniques, real-world examples, and structured activities that reinforce course content and objectives. Provide feedback & coaching to learners in real-time, offering guidance and support to enhance their understanding and skills development. Design and facilitate sessions that teach CX teams how to use AI tools responsibly and effectively in their daily workflows. Leverage AI-assisted tools to enhance participation and personalization during live training. Uses insights from AI-driven learning platforms to tailor discussions, provide targeted feedback, and reinforce learning outcomes. Instructional Design & Communications Lead comprehensive course design efforts, driving innovation and continuous improvement in learning materials and methods to ensure they meet the evolving needs of the CX team and broader business. Take full ownership of content development, acting as the final point of quality control for course content updates and ensuring that all learning materials are aligned with strategic business goals. Develop and manage high-level communication strategies for learning initiatives, collaborating with leadership and cross-functional teams to ensure alignment and stakeholder buy-in. Integrate AI-enabled design approaches into curriculum development to improve personalization, scalability, and learner engagement. Uses AI-enabled authoring tools to rapidly prototype, script, and iterate on training materials. Program Management Manage complex, high-visibility learning programs from end to end, with full accountability for program success, continuous improvement, and alignment with business outcomes. Oversee multiple CX Academy cohorts simultaneously, ensuring efficient cohort management and providing strategic guidance on program implementation and learner success. Monitor participant progress and engagement, proactively identifying and addressing potential barriers to success. Identify and drive improvements across programs, utilizing feedback from participants and stakeholders to evolve learning offerings and ensure continued alignment with business goals. Operationalize AI tools to automate repetitive program administration tasks where appropriate. Implement AI-assisted project tracking, communication, and reporting tools to streamline coordination and status visibility. Stakeholder Management Serve as a primary contact for high-level stakeholders, developing and maintaining strategic relationships to ensure learning programs are aligned with business priorities. Collaborate with senior leadership and department heads, providing expert consultation to design learning initiatives that directly support organizational growth and CX effectiveness. Influence and negotiate with stakeholders at all levels, ensuring alignment between learning objectives and business needs, while also representing the voice of the CX L&D team in broader strategic discussions. Use AI-supported data visualization and summary tools to synthesize stakeholder feedback and present actionable insights. Communicates the value and limitations of AI-assisted solutions to stakeholders, ensuring transparency and alignment with organizational standards. Data & Analytics Own the learning data strategy for key programs, using sophisticated data analysis to assess program effectiveness, identify trends, and provide strategic insights to leadership. Lead data-driven decision-making by tracking key performance indicators (KPIs) such as learner progress, program impact, and ROI, using this data to continuously optimize learning experiences. Support other team members in developing their data analysis skills, helping them to understand and apply the Kirkpatrick Model of Training Evaluation data to their own work. Leverage AI-derived insights to personalize learning and measure AI-enabled program effectiveness. Leverages AI-powered analytics dashboards to identify learning trends, skill gaps, and opportunities for performance support. Translates AI-derived insights into clear, actionable recommendations for program optimization. Here’s What We're Looking For 5+ years of L&D experience required Ability to travel up to 50% of the time Proactive, solution-oriented mindset with excellent organizational skills and attention to detail. Adaptability and a passion for continuous learning and personal development in a fast-paced, dynamic environment. Proven experience in learning program design, development, and facilitation across multiple knowledge areas. Strong coaching skills, with the ability to mentor learners and participants as well as junior team members. Expertise in managing end-to-end learning programs, including cohort management and continuous improvement. Excellent stakeholder management skills, with a track record of building strong relationships and aligning learning initiatives with business goals. Data-driven mindset, with the ability to analyze program outcomes and use insights for continuous enhancement. Strategic thinker with a passion for driving business impact through learning and development. Ability to thrive in a fast-paced, dynamic environment and manage multiple priorities effectively. Strong communication skills, with the ability to engage and influence stakeholders at all levels. 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. Experience evaluating or implementing AI-enabled learning platforms. Our cash compensation amount for this role is $91,065/yr to $112,314/yr in Denver & most major metro locations, and $110,640/yr to $136,456/yr for San Francisco & New York. Final offer amounts are determined by multiple factors including candidate location, experience and expertise and may vary from the 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. Gusto takes security and protection of your personal information very seriously. 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