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Salary: USD 108,466 - 162,698 / annual
Castlight Health is seeking a Lead, Channel Enablement to own the enablement strategy and infrastructure supporting the sale of Castlight-powered solutions through a channel ecosystem including health plans, strategic partners, resellers, and Marketplace relationships. This role reports to the Director of GTM Enablement and serves as the commercial owner of the second-sale enablement motion, acting as connective tissue across Castlight, partners, and go-to-market teams.
Key Responsibilities:
Channel & Partner Enablement: Build and own the channel enablement strategy across health plans, strategic partners, resellers, and Marketplace partners. Develop scalable enablement programs that help partner sellers understand buyer problems, articulate Castlight's value proposition, demonstrate solutions, and advance opportunities. Create partner-ready training programs, playbooks, talk tracks, FAQs, objection handling guides, templates, and selling tools aligned with Product Marketing's approved positioning. Partner with Strategic Partnerships to build tailored enablement programs based on partner type, commercial model, seller audience, and go-to-market motion. Support launch and ongoing readiness of new partner relationships and Castlight-powered offerings.
Second Sale Enablement: Own the enablement framework for the second-sale motion across health plan and partner channels. Establish a single source of truth for second-sale training, demos, tools, templates, and selling standards. Prepare Castlight Commercial and Client teams for the transition of second-sale execution to Client CSMs by September 30. Build repeatable training and certification approaches allowing Client teams to execute consistently while maintaining Commercial standards. Create scalable processes for Commercial review, feedback, and continuous improvement as execution moves closer to client and health plan teams.
Demo Strategy & Engineering: Own core demo environments supporting health plan, partner, reseller, and second-sale motions. Build and maintain Figma-based demos, screen libraries, reusable components, and partner-specific demo experiences. Maintain demo environments as products, capabilities, positioning, and user experiences evolve. Lead Nova conversions across the existing channel book and establish standards for new partner implementations. Manage partner access to demo environments and establish governance around version control, usage, and updates. Coordinate external design or Figma resources as needed. Establish regular operating cadence with Product, UX, Solutions, and Product Marketing to keep demo experiences accurate and current.
Cross-Functional Enablement: Translate Product Marketing's positioning and messaging into usable seller training, demos, and field tools. Partner with Strategic Partnerships to understand partner priorities, seller needs, and commercial opportunities. Partner with Client leadership to ensure second-sale teams have tools, training, and confidence to execute. Partner with Solutions and Product teams to keep demonstrations accurate and identify opportunities to improve how Castlight capabilities are represented in market. Bring health plan, partner, seller, and field feedback back to Product Marketing, Product, Solutions, and Strategic Partnerships to improve messaging, products, and partner experience.
Success Metrics: Partner sellers can confidently explain and demonstrate Castlight-powered solutions without relying on Castlight for every interaction. Health plan and partner channels have consistent, current, easy-to-use enablement resources. Second-sale execution successfully transitions to Client teams without losing quality or commercial consistency. Demo environments stay aligned with live product and can be efficiently adapted across partners and channels. New partners move from agreement to seller readiness through repeatable enablement process. Feedback from partner and second-sale motions consistently reaches teams responsible for product, messaging, and commercial strategy.
Qualifications:
- 4+ years of experience in sales enablement, partner enablement, solutions consulting, product marketing support, or related commercial role, ideally within healthcare technology, employee benefits, or health plans
- Experience building enablement programs for channel, partner, reseller, or indirect sales teams
- Demonstrated ability to translate complex products and positioning into practical tools sellers can use
- Experience building and maintaining demo environments at scale
- Strong Figma skills with ability to manage production-quality demo environments, reusable components, and screen libraries
- Strong training and facilitation skills across both internal and external seller audiences
- Excellent project management skills with ability to coordinate Product, UX, Product Marketing, Client, Commercial, and external agency partners
- Working knowledge of health plan go-to-market models, white-labeled solutions, or embedded technology partnerships
- Comfortable operating in environment where ownership crosses organizational boundaries and success depends on influence, structure, and follow-through
