Castlight Health

• Own end-to-end delivery for the organization's most complex, high-priority client implementations, serving as the primary accountable party. • Develop and maintain the implementation methodology, including playbooks, escalation frameworks, and quality standards. • Partner with sales, consulting, and product teams to design implementation approaches for new clients, markets, or product lines. • Synthesize client feedback, operational data, and stakeholder input to drive continuous improvement in implementation outcomes. • Lead root cause analyses on implementation failures and develop corrective action plans. • Represent implementation in cross-functional strategic discussions and product development forums. • Mentor senior consultants and lead the knowledge development agenda for the implementation team.

• Lead a team of implementation consultants • Develop implementation capacity plans • Drive quality and consistency across client implementations • Coach and develop senior implementation professionals • Represent the implementation team in cross-functional forums

• Set the strategic vision for customer success across the organization, defining engagement models, success metrics, and client lifecycle frameworks. • Own relationships with the most strategically significant clients, personally engaging at the executive level on matters of program direction, escalation, and growth. • Lead design and continuous refinement of customer success infrastructure, including health scoring, QBR formats, and data-driven retention frameworks. • Partner with sales, clinical, and product leadership to align customer success strategy with enterprise commercial and product priorities. • Evaluate and drive adoption of technology and tooling that scales customer success capabilities across the team. • Lead customer success professionals, setting quality expectations, establishing team standards, and developing functional expertise. • Synthesize portfolio-level performance insights to advise senior leadership on client satisfaction, retention risk, and expansion opportunity.

• Write and optimize complex SQL queries in BigQuery to extract, clean, and model data for reporting. • Design, build, and maintain high-performance automated dashboards in Tableau. • Interface with Airflow to monitor data workflows and ensure reporting accuracy and freshness. • Partner with business leaders to define KPIs and present findings that drive departmental strategy. • Assist in the potential migration or implementation of Looker for self-service analytics.

• 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.

• Build and nurture strong relationships with strategic partners, championing Castlight Health’s mission and the value of our Ecosystem. • Collaborate cross-functionally with sales, customer success, marketing, finance and partners to unlock shared revenue opportunities and maximize revenue growth with partners. • Act as the primary point of contact for partners including development and execution of joint go-to-market initiatives, client launches and escalations. • Proactively establish and monitor performance objectives, financial targets, and critical milestones that ensure a productive partner relationship. • Develop strong relationships with ecosystem partners, including at the executive level, and incorporate other internal teams, when needed. • Organize partnership-related events and drive initiatives that improve our stickiness within the market and for our clients and members. • Monitor the health and performance of partners. • Use data-driven insights to optimize strategies and decision-making.

• Lead the planning, development, and execution of GTM plans for new product releases and feature enhancements • Develop and evolve positioning and messaging that clearly articulates the value of Castlight’s products to diverse audiences (employers, brokers/consultants, health plans) • Produce high-quality sales and marketing enablement materials, including decks, one-pagers, battle cards, product briefs, FAQs, and training guides • Partner with Sales, Customer Success, and Marketing to provide the tools, playbooks, and training needed to confidently communicate product value and competitive differentiation • Conduct market research and competitive analysis to identify trends, customer needs, and opportunities to improve Castlight’s market position • Gather and synthesize voice-of-customer insights to inform product roadmap decisions and refine marketing strategies • Define success metrics for launches and campaigns, analyze performance, and iterate on learning to optimize impact

• Partner with product leadership to ensure roadmaps and key deliverables are well-tracked and executed • Maintain & create dashboards to monitor KPIs and key results • Lead the adoption of new processes and tools • Serve as a power user for project management tools (e.g., Jira, Confluence) • Support communication and alignment between Product, Engineering, Design, and GTM teams • Provide peer guidance and maintain high standards for product documentation and internal communication frameworks

• Support and scale multiple engineering teams, recruiting top-tier talent to execute on an aggressive and meaningful product roadmap. • Partner closely with product, design, and architecture leaders to turn complex ideas and care journeys into simple user realities. • Own the outcomes of your organization, ensuring the technology you oversee is fast, accurate, and high-performing. • Cultivate a culture of high-quality execution and continuous delivery where accountability is everything.

• Understand our full ecosystem of users + platforms, and work to build an AI experience strategy that solves critical problems for each type of user in their workspace. • Help to evolve our experiences from mostly conversational AI to agentic and predictive AI, embedding the technology in various workflows in ways that don’t require question/answer. • Work across the design process at many levels: from the “30,000 ft” view to the interaction details that makes an experience feel sophisticated. • Work with visual designers to help shape the look & feel and voice & tone of AI across platforms. • Incorporate motion design and visual affordances that help the user know where AI has been applied and in what ways. • Work closely with PMs and engineers to understand requirements, possibilities, and limitations of the system, and craft release plans that build towards a shared vision. • Create clear documentation for AI-driven experiences so other teams and designers can work with your AI system. • Stay on top of AI trends and technological advancements, ensuring that our practices are at the forefront of the industry and continuously evolving. • Bring new processes, ideas, and ways of working back to the UX team and our product and engineering partners. • Be a strong and positive role model and mentor for a growing design team, fostering a culture of design excellence. • Chip in to other areas of work as needed. • Work to stand up new practices and lead aspects of team development to create an organization that is smart, talented, and has fun working together!