# Head of Customer & Field Learning

**Company:** [RSA](https://hotfix.jobs/companies/rsa)
**Location:** Burlington, MA
**Role:** Customer Success
**Experience:** 8+ years
**Skills:** artificial intelligence, Conversational AI, Prompt Engineering, Workflow Automation, Instructional Design, learning experience design, customer education, product adoption, Coaching, adult learning, performance measurement, cross-functional communication
**Posted:** 2026-08-07

> 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.

## Job Description

## 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.

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