GTM Enablement Director

Castlight Health

Director of GTM Enablement driving sales execution and effectiveness at Castlight Health. Leading a small team and working closely with Sales, Marketing, and Product Marketing to improve performance.

Posted 5/26/2026full-timeRemote • 🇺🇸 United StatesLead💰 $144,368 - $216,552 per yearWebsite

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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.

Benefits

Comp & perks

Health insurance
Retirement plans
Professional development opportunities

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

sales enablementGTMsales executiontraining deliverydata analysispipeline managementobjection handlingbusiness case developmentsales strategycompetitive positioning

Soft Skills

communicationinfluenceaccountabilitycollaborationleadershipprioritizationadaptabilityproblem-solvingcoachingcurriculum development