Job Description Summary

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Castlight is hiring a Director of GTM Enablement to improve how our teams sell, position, and execute in the market. This is a high-impact, player-coach role. You will lead a small team while personally driving internal enablement, field execution, and sales effectiveness across our GTM organization. You will work closely with Growth, Sales, Marketing, and Product Marketing to ensure our teams have the knowledge, tools, and consistency needed to create pipeline and close business. This role is not about running training programs in isolation. It is about improving performance in the field.

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How will you make an impact & Requirements

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About Castlight

Castlight Health is a leader in healthcare navigation, helping employers and health plans improve outcomes and reduce costs through data, clinical guidance, and a connected care experience. We bring together navigation, advocacy, and care delivery to help people make better healthcare decisions and get the most from their benefits.

What You'll Do

• 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.

Translate Strategy into Field-Ready Execution

• 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.

• Embed clarity into the field so teams know how to tell the story, handle resistance, and move deals forward.

Use Pipeline Insight to Drive Enablement Priorities

• 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.

Enable Sales Process and Tools

• 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.

Lead a Lean Team

• 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.

What Success Looks Like

• Sales teams can clearly and consistently articulate Castlight’s value.

• Deals progress more efficiently through each stage.

• Product knowledge and competitive confidence improve across the field.

• Lighting the Way becomes a core driver of sales effectiveness.

• Enablement is directly tied to pipeline movement and outcomes.

What We're Looking For

• 8+ years of experience in sales enablement, GTM, or commercial roles.

• Experience improving sales execution and field performance.

• Strong understanding of B2B sales processes, ideally in healthcare, SaaS, or benefits.

• Ability to translate complex products into simple, actionable sales guidance.

• Experience delivering training that drives behavior change, not just knowledge transfer.

• Comfort working with data to inform priorities, including pipeline and stage progression.

• Strong communicator with the ability to influence across Sales, Marketing, Product Marketing, and Growth leadership.

Who You Are

• A builder and operator who thrives in a lean environment.

• Focused on outcomes, not just activity.

• Comfortable working directly with sales teams and leaders.

• Pragmatic, hands-on, and focused on what actually works in the field.

Why This Role

• Direct impact on pipeline progression and revenue outcomes.

• High visibility across Growth and Sales leadership.

• Opportunity to build and scale a core GTM capability at Castlight.

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Compensation:

$144,368.00

to

$216,552.00