Head of Customer & Field LearningRSA is looking for a different kind of enablement leader: someone who is AI-first, learning-obsessed, and focused on measurable behavior change.
This is not a traditional sales enablement role built around decks, webinars, and training calendars. The job is to build learning systems that help customers, partners, and field teams adopt new products, new motions, and new ways of working.
Principal 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.
- Turn complex product and customer strategy into practical learning experiences people actually use.
- Create measurement systems that show whether people are learning, applying, and improving.
- Partner across Product, Marketing, Sales, Customer Success, Support, Services, and Operations.
Skills:- Deep curiosity about how adults learn, retain, practice, and change behavior.
- Hands-on interest in AI and how it transforms 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 - beyond completion rates to actual behavior and impact.
- Builder mentality: comfortable testing, prototyping, improving, and operating in ambiguity.
- Strong cross-functional influence and communication skills.
Relevant Backgrounds Could Include- Customer learning or customer education
- Product adoption or product engagement
- Instructional design / 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 Looks Like- 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 become useful enough that people choose to use them.
- Customers adopt faster and with less friction.
- RSA can measure whether learning is changing capability, confidence, adoption, and outcomes.
The Person We WantThe ideal candidate is part learning designer, part AI experimenter, part operator, and part teacher. They care less about running enablement events and more about building systems that help people get better.
They are energized by complex customer journeys, real-world constraints, and the chance to turn learning into customer and business outcomes.
Full-time, non-Sales US employees are also eligible for annual discretionary bonuses that are funded based on prior year company performance. RSA Sales team members are eligible to participate in company commission plans.
In addition, RSA offers its eligible US employees a comprehensive array of benefit programs including flexible paid-time-off, health, disability, and life insurance, and a 401(k) retirement plan with company matching contributions.
