Senior L&D Specialist

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.