Castlight Health

Product Marketing

• Drive sales execution and effectiveness across the full commercial motion, improving how reps operate through the sales process from Discovery to Evaluation to Close
• Identify where deals stall and implement targeted fixes that improve execution, consistency, and selling confidence
• Drive consistency in how Castlight is positioned and sold across core segments, including Employer, Health Plan, and Consultant motions
• Partner with Sales leadership to reinforce best practices, sharpen selling behaviors, and improve performance in the field
• Own Lighting the Way Design and lead Lighting the Way, Castlight’s core GTM enablement program
• Deliver a structured curriculum across product knowledge, competitive positioning, core messaging, and value articulation
• Run ongoing sessions tied to real field needs, including discovery, business case development, objection handling, and deal strategy
• Ensure learning translates into improved execution, not just attendance
• Partner with Product Marketing to turn messaging into practical talk tracks, sales narratives, and objection handling
• Ensure materials are usable in live selling, not just well-written
• Leverage pipeline data and deal feedback to identify gaps in execution
• Partner with RevOps to understand trends in stage progression, conversion, and where additional reinforcement is needed
• Prioritize enablement efforts based on what will most improve pipeline movement and sales outcomes
• Ensure reps understand what good looks like at each stage of the sales process
• Embed guidance into workflows, tools, and sales materials so the field can find and use what they need
• Drive adoption of enablement content and practices across the organization
• Manage one RevOps resource focused on data, reporting, and systems support
• Manage one Partner Enablement specialist focused on reseller and health plan channels
• Set priorities, drive accountability, and stay close to execution
• Step in directly where needed in a lean environment.

GTM Enablement Director