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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. We are seeking a Senior Learning & Development Specialist to lead program design, facilitate learning, and manage stakeholder relationships to drive business success.

Responsibilities

Facilitate in-person, virtual, and hybrid learning sessions across at least six distinct and complex knowledge areas.
Create an inclusive and dynamic learning environment that challenges participants to apply critical thinking and problem-solving skills.
Engage learners through interactive techniques, real-world examples, and structured activities.
Provide feedback & coaching to learners in real-time.
Design and facilitate sessions that teach CX teams how to use AI tools responsibly and effectively.
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.
Lead comprehensive course design efforts, driving innovation and continuous improvement in learning materials and methods.
Take full ownership of content development, acting as the final point of quality control for course content updates.
Develop and manage high-level communication strategies for learning initiatives.
Integrate AI-enabled design approaches into curriculum development.
Use AI-enabled authoring tools to rapidly prototype, script, and iterate on training materials.
Manage complex, high-visibility learning programs from end to end.
Oversee multiple CX Academy cohorts simultaneously.
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.
Operationalize AI tools to automate repetitive program administration tasks.
Implement AI-assisted project tracking, communication, and reporting tools.
Serve as a primary contact for high-level stakeholders, developing and maintaining strategic relationships.
Collaborate with senior leadership and department heads, providing expert consultation to design learning initiatives.
Influence and negotiate with stakeholders at all levels.
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.
Own the learning data strategy for key programs, using sophisticated data analysis to assess program effectiveness.
Lead data-driven decision-making by tracking key performance indicators (KPIs).
Support other team members in developing their data analysis skills.
Leverage AI-derived insights to personalize learning and measure AI-enabled program effectiveness.
Leverage 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.

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.
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.

Skills

AI tools
Prompt engineering
APIs/integrations
Content creation
Data analysis
Learner engagement
AI-enabled learning platforms
Learning program design
Learning program development
Learning program facilitation
Coaching
Stakeholder management
Data analysis
Communication

Location

Denver
San Francisco
New York City
Scottsdale

Work Type

Hybrid
Full-time

Experience Level

Senior
5+ years of L&D experience

Salary/Compensations

$85,955/yr to $107,000/yr in Denver & Phoenix
$110,640/yr to $130,000/yr for San Francisco & New York

Benefits

Competitive base pay
Benefits
Equity (RSUs)

About the Company

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, Colorado, San Francisco, California, and New York City, New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve.
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.

Equal Opportunity

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.