Outbound Squad Sales Enablement Masterclass with VP of Sales Enablement at Rippling, Jonas Master
Jan 27, 2026
Jonas Master, VP of Sales Enablement at Rippling, leads a large enablement org focused on measurable behavior change. He discusses prioritizing one to two outcomes, partnering with sales leaders as a thought partner, choosing the right trainers, using a single golden metric and tools like Gong for attribution, and turning managers into reinforcement multipliers.
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Joining Rippling And Rapid Growth
- Jonas joined Rippling after being approached to lead enablement and saw massive product-market opportunity.
- He scaled the enablement team from seven to over thirty to support growth from ~400 to 1,800 sellers.
Make Reinforcement The Priority
- Treat training as one component; design reinforcement, measurement, and manager enablement around the outcome.
- Leverage non-training tactics (dashboarding, exemplar calls, manager coaching) to sustain behavior change.
Use Experts To Model And Managers To Teach
- Use subject-matter experts to present and model skills; enablement should facilitate practice and feedback.
- Turn top performers and managers into presenters, then run role-play and iterative practice sessions.