Senior L&D Specialist

At Gusto, we're on a mission to grow the small business economy.

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.

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.
• 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.

Requirements

• 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.

Compensation 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.