Senior Learning & Development Specialist

About Gusto: Gusto is on a mission to grow the small business economy by handling payroll, health insurance, 401(k)s, and HR, allowing owners to focus on their craft and customers. With teams in Denver, San Francisco, and New York, Gusto supports over 500,000 small businesses nationwide.

All full-time employees receive competitive base pay, benefits, and equity (RSUs). AI is a fundamental part of Gusto’s operations, and all team members are expected to engage with AI tools relevant to their roles.

About the Role: The CX Learning & Development team is dedicated to building exceptional customer experiences by equipping CX professionals with the skills they need. This role involves leading program design, facilitating learning, and managing 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 the Learning & Development team within Gusto’s Customer Experience organization, which is pivotal in maintaining industry-leading NPS scores and serving over 500,000 customers.

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, tailoring delivery for various audience levels, including mid & senior leadership participants.
• Create an inclusive and dynamic learning environment that challenges participants to apply critical thinking and problem-solving skills in real-world scenarios.
• Engage learners through interactive techniques, real-world examples, and structured activities that reinforce course content.
• Provide real-time feedback and coaching to learners, offering guidance to enhance their understanding and skills development.
• Design and facilitate sessions on teaching 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.
• Use 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 meet evolving needs.
• Take full ownership of content development, ensuring alignment with strategic business goals and acting as the final point of quality control.
• Develop and manage high-level communication strategies for learning initiatives, collaborating with leadership and cross-functional teams.
• Integrate AI-enabled design approaches into curriculum development to improve personalization, scalability, and learner engagement.
• Use 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, ensuring accountability for program success and continuous improvement.
• Oversee multiple CX Academy cohorts simultaneously, providing strategic guidance on program implementation and learner success.
• Monitor participant progress and engagement, proactively addressing potential barriers to success.
• Identify and drive improvements across programs using feedback from participants and stakeholders.
• Operationalize AI tools to automate repetitive program administration tasks.
• Implement AI-assisted project tracking, communication, and reporting tools to streamline coordination.

Stakeholder Management

• Serve as a primary contact for high-level stakeholders, developing strategic relationships to align learning programs with business priorities.
• Collaborate with senior leadership and department heads, providing expert consultation to design learning initiatives that support organizational growth.
• Influence and negotiate with stakeholders to ensure alignment between learning objectives and business needs.
• Use AI-supported data visualization and summary tools to synthesize stakeholder feedback and present actionable insights.
• Communicate the value and limitations of AI-assisted solutions to stakeholders.

Data & Analytics

• Own the learning data strategy for key programs, using sophisticated data analysis to assess program effectiveness and provide strategic insights.
• Lead data-driven decision-making by tracking KPIs such as learner progress, program impact, and ROI, optimizing learning experiences.
• Support team members in developing their data analysis skills, helping them understand and apply the Kirkpatrick Model of Training Evaluation.
• Leverage AI-derived insights to personalize learning and measure AI-enabled program effectiveness.
• Use AI-powered analytics dashboards to identify learning trends, skill gaps, and opportunities for performance support.
• Translate AI-derived insights into clear, actionable recommendations for program optimization.

Here’s what we’re looking for:

• 5+ years of Learning & Development 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 passion for continuous learning in a fast-paced environment.
• Proven experience in learning program design, development, and facilitation across multiple knowledge areas.
• Strong coaching skills, with the ability to mentor learners and junior team members.
• Expertise in managing end-to-end learning programs, including cohort management and continuous improvement.
• Excellent stakeholder management skills, aligning learning initiatives with business goals.
• Data-driven mindset, analyzing program outcomes for continuous enhancement.
• Strategic thinker with a passion for driving business impact through learning.
• Ability to thrive in a fast-paced environment and manage multiple priorities.
• Strong communication skills, engaging and influencing stakeholders at all levels.
• Demonstrated experience designing, implementing, and evaluating AI-enabled learning solutions.
• Experience experimenting 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, including familiarity with LLMs, prompt engineering, and APIs/integrations.
  • Familiarity with AI tools supporting 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.
  • Experience evaluating or implementing AI-enabled learning platforms.