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RSARSABurlington, MA

Head of Customer & Field Learning

Leads AI-first learning systems for customers, partners, and field teams, translating complex product and customer strategy into role-based experiences that improve adoption and performance. Requires experience in customer education, instructional design, enablement, or performance improvement, plus strong measurement and cross-functional influence.

Salary not listed
On-site8+ YOECustomer Success

About the role

Responsibilities

  • Build AI-enabled learning programs that improve capability, confidence, adoption, and performance.
  • Design role-based learning paths for Sales, Customer Success, Support, Services, Partners, and Customers.
  • Use AI to improve practice, coaching, reinforcement, knowledge access, and adoption.
  • Translate complex product and customer strategy into practical learning experiences.
  • Create measurement systems that assess whether people are learning, applying, and improving.
  • Partner across Product, Marketing, Sales, Customer Success, Support, Services, and Operations.

Requirements and Qualifications

  • Deep curiosity about how adults learn, retain, practice, and change behavior.
  • Hands-on interest in AI and its impact on learning, coaching, content, and workflows.
  • Experience in customer education, learning design, enablement, adoption, instructional design, or performance improvement.
  • Ability to simplify complex ideas into clear, useful learning experiences.
  • Strong measurement mindset, extending beyond completion rates to behavior and impact.
  • Builder mentality, with comfort testing, prototyping, improving, and operating in ambiguity.
  • Strong cross-functional influence and communication skills.

Relevant Backgrounds

  • Customer learning or customer education
  • Product adoption or product engagement
  • Instructional design or learning experience design
  • Customer success enablement
  • Partner or customer onboarding
  • AI-enabled learning tools, conversational AI, prompt engineering, or workflow automation
  • Teaching, coaching, facilitation, or adult learning

Success Measures

  • Customers, partners, and field teams know what to do differently, not just what to know.
  • Managers have better tools to coach and reinforce new behaviors.
  • AI-enabled learning resources are useful enough that people choose to use them.
  • Customers adopt faster and with less friction.
  • Learning can be measured through changes in capability, confidence, adoption, and outcomes.

Compensation and Benefits

  • Full-time, non-Sales US employees are eligible for annual discretionary bonuses funded based on prior-year company performance.
  • Eligible US employees receive benefits including flexible paid time off, health, disability, and life insurance, and a 401(k) retirement plan with company matching contributions.

Skills

artificial intelligenceConversational AIPrompt EngineeringWorkflow AutomationInstructional Designlearning experience designcustomer educationproduct adoptionCoachingadult learningperformance measurementcross-functional communication
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