GTM Enablement Director

🕒 May 26

🇺🇸 United States – Remote

💵 $144.4k - $216.6k / year

⏰ Full Time

🔴 Lead

🎁 Product Marketing

🦅 H1B Visa Sponsor

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Castlight Health

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2008

☁️ SaaS

⚕️ Healthcare Insurance

🤝 B2B

SaaS • Healthcare Insurance • B2B

Castlight Health is a healthcare navigation company that offers a SaaS-based benefits and care navigation platform for employers, health plans, benefit consultants, and digital health partners. The company centralizes employees' health and wellbeing programs in a single digital hub, leveraging aggregated data, integrations, and machine learning alongside live Care Guides and clinical experts to drive engagement, improve preventive care, and reduce costs. Castlight partners with enterprise customers and payers to connect ecosystems of digital health vendors and deliver measurable outcomes such as increased screening, higher wellness visit rates, and medical spending reductions.

📋 Description

• 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

• 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

• Health insurance • Retirement plans • Professional development opportunities