Lead, Channel Enablement

Job Description Summary ‎ Commercial Organization | GTM Enablement Reports to: Director, GTM Enablement The Lead, Channel Enablement owns the enablement strategy and infrastructure that helps Castlight-powered solutions get sold effectively through our channel ecosystem, including health plans, strategic partners, resellers, and Marketplace relationships. This role is the Commercial owner of the second sale enablement motion and the connective tissue across Castlight, our partners, and the teams responsible for bringing our solutions to market. The Lead builds the training, demos, tools, and repeatable programs that allow partner sellers and Castlight teams to confidently position, demonstrate, and sell Castlight-powered solutions at scale. The role also owns the core demo infrastructure supporting channel selling, ensuring our Figma environments, screen libraries, and partner-specific experiences stay current as the product evolves. ‎ How will you make an impact & Requirements ‎ What You'll Own 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 the buyer problem, articulate the Castlight value proposition, demonstrate the solution, and advance opportunities. Create partner-ready training programs, playbooks, talk tracks, FAQs, objection handling, templates, and selling tools using Product Marketing's approved positioning and messaging. Partner with Strategic Partnerships to build tailored enablement programs based on partner type, commercial model, seller audience, and go-to-market motion. Support the 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 one 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 that allow Client teams to execute consistently while maintaining Commercial standards. Create scalable processes for Commercial review, feedback, and continuous improvement as execution moves closer to the client and health plan teams. Demo Strategy & Engineering Own the 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 the standards for new partner implementations. Manage partner access to demo environments and establish clear governance around version control, usage, and updates. Coordinate external design or Figma resources as needed to maintain and scale the demo platform. Establish a regular operating cadence with Product, UX, Solutions, and Product Marketing so demo experiences remain 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 the tools, training, and confidence required 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 the partner experience. How Ownership Works This role operates across several teams, with clear ownership boundaries: Product Marketing owns core positioning, messaging architecture, value propositions, competitive strategy, and master marketing assets. Channel Enablement turns that strategy into training, demos, playbooks, tools, certification, and scalable seller experiences. Strategic Partnerships owns partner strategy, relationships, commercial agreements, partner performance, and escalations. Client CSMs own plan-specific second sale execution, including training delivery to health plan sellers and ongoing maintenance of client-specific materials. Solutions and Product provide product expertise, roadmap input, and validation required to keep demonstrations technically accurate. What Success Looks Like Partner sellers can confidently explain and demonstrate Castlight-powered solutions without relying on Castlight for every selling 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 the live product and can be efficiently adapted across partners and channels. New partners can move from agreement to seller readiness through a repeatable enablement process. Feedback from partner and second sale motions consistently reaches the teams responsible for product, messaging, and commercial strategy. Qualifications 4+ years of experience in sales enablement, partner enablement, solutions consulting, product marketing support, or a 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 that sellers can use. Experience building and maintaining demo environments at scale. Strong Figma skills with the 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 the 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 an environment where ownership crosses organizational boundaries and success depends on influence, structure, and follow-through. What Makes Someone Great in This Role You are equal parts builder, trainer, and operator. You can take a product strategy or message and turn it into something a seller can actually use. You care about the details of a demo experience, but you also understand the commercial outcome it is supposed to drive. You are comfortable working across teams, creating structure where it does not yet exist, and building enablement that scales beyond Castlight's own sales force. ‎ Compensation Range: $108,466.00 to $162,698.00 The anticipated base salary range represents the Company's good-faith estimate of the compensation it reasonably expects to pay for this position at the time of posting. Actual compensation will be determined based on factors including experience, skills, qualifications, geographic location, internal equity, and business needs.