Headspace

Community Manager

• Deliver engaging, high-quality virtual and in-person training experiences for strategic enterprise clients and partners, with the goal of driving Headspace adoption and employee engagement.
• Facilitate sessions on mental health and well-being topics with confidence, care, and credibility, reflected in consistent positive client feedback.
• Support client launches, key meetings, and high-impact moments as a trusted facilitator and thought partner.
• Support with cross-functional event coordination for strategic accounts and events.
• Drive and evolve Headspace’s Champions and Community programs, developing products and experiences that engage champions and leaders within client organizations.
• Own the day-to-day experience of the Client Admin Community, including moderation, programming, forums, meetups, and events.
• Act as a consultative partner to enterprise clients, helping shape engagement strategies and recommending relevant training and community experiences.
• Partner closely with the Client Success team to support high-impact and higher-complexity enterprise accounts, contributing to long-term client success and reduced risk.
• Create new and update existing Headspace training content in response to client feedback, business needs, and team strategy.
• Support training and engagement projects from concept through delivery, collaborating with leadership and cross-functional partners to solve challenges and build scalable solutions.
• Design net-new trainings and engagement products from a blank slate, aligned with Headspace’s brand, voice, and design principles.
• Support the training and ongoing development of Headspace’s internal and external facilitator network.
• Contribute to strategic team initiatives as priorities evolve, which may include building new engagement products, improving processes, supporting data analysis, or enabling internal teams.
• Commit to ongoing personal and professional development, including continued learning in mental health, facilitation, and Headspace content.

Client Training, Community Manager

Product Marketing

• Own B2B product positioning, messaging, and packaging across Headspace’s Mental Health Companion offerings, ensuring clear differentiation for employers, health plans, and benefits consultants
• Craft buyer- and influencer-centric storytelling that translates Headspace’s end-to-end mental healthcare model into compelling value propositions for employers, health plans, and benefits consultants
• Develop high-impact external assets (sales decks, consultant-facing materials, narratives, launch messaging, thought leadership) and internal enablement tools that support all phases of the sales cycle, in close partnership with Commercial teams
• Lead commercialization and go-to-market strategy for new and existing B2B products and features, from early narrative development through full-funnel activation
• Act as a strategic thought partner to Product, shaping the roadmap through deep understanding of customer needs, benefits consultant influence, market dynamics, and competitive landscape
• Synthesize insights from the field—including feedback from customers, sales, partners, and benefits consultants—to inform positioning, prioritization, and business strategy
• Serve as connective tissue across teams, aligning Product, Commercial, Marketing, Clinical, Member Support, and Communications around a shared go-to-market narrative
• Champion the Mental Health Companion category, helping Headspace define and lead this space through strong points of view, consistent language, and differentiated storytelling

Director, B2B Product Marketing

Proposal Manager

• Lead and project manage the end-to-end RFP/RFI process, from initial intake to final submission, in partnership with Sales leaders and Account Managers.
• Draft persuasive, clear, and differentiating content that aligns with Headspace’s brand voice and unique market positioning.
• Intake, assess, and triage RFPs from employers, consultants, and health plans, developing case-specific "win strategies" alongside Sales leadership.
• Support the sales team with post-proposal follow-up questions and additional documentation.
• Own and maintain assigned sections of the proposal content database, ensuring all technical and product information is accurate and up to date.
• Refresh messaging to reflect ongoing product enhancements, outcomes, and evolving market trends.
• Build strong cross-functional relationships with internal Subject Matter Experts (SMEs) and external business partners to streamline information gathering.
• Coordinate across departments—including Finance, Legal, Security, and Care teams—to ensure proposal content meets compliance and technical standards.
• Manage competing priorities to consistently meet all internal and external deadlines.
• Support ad-hoc projects and take on additional responsibilities as the Proposal team evolves.

Product Manager

• Define the long-term vision and strategy for the Personalization Foundations platform
• Own the centralized user and content data layers
• Lead the product strategy and execution for key workstreams
• Lead the entire product lifecycle for core platform capabilities
• Work closely with Engineering, Science, and Product Design to define and prioritize requirements
• Partner cross-functionally with consuming Product teams, Engineering, Data Science, and Legal
• Establish clear metrics for platform success and rigorously track and report on performance
• Provide technical and product oversight for complex projects and actively mentor junior members

Staff Product Manager – Personalization

• Define and own the vision, strategy, and roadmap for LLM-based product innovation across Headspace
• Identify, prototype, and validate high-impact generative AI use cases in partnership with engineering, research, and design
• Translate complex LLM capabilities into intuitive, valuable user experiences
• Drive cross-functional alignment across product, data science, design, go-to-market, and operations
• Establish scalable frameworks, best practices, and reusable systems for LLM integration
• Evaluate external tools, vendors, and partnerships to inform build vs. buy decisions
• Define success metrics and KPIs to ensure LLM initiatives deliver measurable user and business outcomes
• Serve as an internal thought leader and champion for responsible, forward-looking AI innovation

Principal Product Manager – LLM Innovation

Account Executive

• Own and exceed your quota by closing new logo deals with employers of 7,500+ employees, selling high-ACV (Six and Seven-Figure) multi-product contracts.
• Manage full-cycle enterprise sales processes including outbound prospecting, discovery, consultative pitching, product demonstration, proposal development, negotiation, and close.
• Cultivate trusted relationships with senior leaders across Human Resources, Total Rewards, Benefits, and People teams to deeply understand organizational needs and priorities.
• Collaborate closely with Account Development Executives (BDRs), Consultant Relations, and Marketing to build pipeline and support coordinated regional go-to-market efforts.
• Partner with key benefits consultants, brokers, and channel partners to amplify market reach and co-sell effectively.
• Serve as a strategic expert in the mental health benefits space, leveraging industry trends, buyer insights, and competitive dynamics to shape your sales approach.
• Lead the development of strategic solutions to technical sales challenges, partnering with Sales Ops and leadership to shape sales methodologies and standards.
• Provide accurate forecasting and pipeline reporting to support revenue planning and team-wide accountability.
• Partner with Sales Ops and leadership to refine and implement sales excellence processes that support consistency across enterprise deals.
• Identify market trends and propose innovative solutions in collaboration with cross-functional teams to support long-term business opportunities.
• Represent Headspace at high-impact industry events and conferences to enhance brand presence and cultivate new enterprise relationships.
• Contribute to organizational capability building by sharing best practices, coaching peers, and identifying learning opportunities to strengthen sales team effectiveness.
• Travel as needed (~30%) to advance key deals and attend in-person meetings or events.

Sales Executive, Enterprise

Program Manager

• Own AI intake and prioritization: triage requests, refine problem statements, size value, and maintain a transparent queue.
• Lead small–medium AI initiatives end-to-end (discovery → pilot → launch), aligning scope, milestones, success metrics, and stakeholders.
• Build and run AI enablement (training, office hours, playbooks, and an AI Champions network) to drive adoption and fluency.
• Grow awareness and adoption of existing AI tools with functional leaders to expand use cases and impact.
• Standardize AI vendor evaluation and guide tools through governance with Product, Legal, Privacy, Security, Procurement.
• Champion responsible AI through measurement, training, and org-wide communication.
• Deliver lightweight reporting and exec-ready updates on pipeline health, outcomes, and trade-offs.
• Unblock high-leverage technical/integration work and identify next-wave AI opportunities to scale adoption and cultural change.

AI Enablement Program Manager

• Define and own the product vision, strategy, and multi-year roadmap for Health Plan and Employer solutions.
• Translate market trends (healthcare, benefits, employer wellness, payer innovation) into differentiated product opportunities.
• Ensure product strategy aligns with Headspace’s clinical model, evidence standards, and business objectives.
• Build, lead, and mentor a team of Product Managers across multiple product areas.
• Establish clear product principles, decision frameworks, and operating rhythms.
• Partner with Product Design and Engineering leadership to drive high-quality execution and innovation.
• Act as the senior product partner to Sales, Partnerships, Customer Success, and Marketing for Health Plans and Employers.
• Collaborate with Clinical, Legal, Compliance, and Data teams to ensure products meet regulatory, clinical, and privacy requirements.
• Influence executive stakeholders with clear narratives, data, and trade-off recommendations.
• Deeply understand the needs of health plan partners, employers, and members, using research, data, and direct customer engagement.
• Drive measurable outcomes across member engagement, clinical impact, partner satisfaction, and revenue growth.
• Lead discovery efforts to validate new offerings, pricing models, and delivery mechanisms.

Director of Product Management, Health Plans – Employer Innovation

Operations

• Lead the scoping, project management, and execution of our FY26 Employee Assistance Program (EAP) Optimization roadmap.
• Own the end-to-end EAP Partner Optimization roadmap, including quarterly and annual planning – as well as outcomes.
• Inform and translate FY26 strategic objectives into clear scopes, timelines, milestones, and success metrics.
• Identify and prioritize portfolio of optimization opportunities across multiple partners aligned to shared goals.
• Drive scoping and execution of multiple complex, cross-functional initiatives that improve operational efficiency and partner integration.
• Establish and refine operational frameworks, documentation, and role & responsibility models with partners.
• Serve as the operational owner for internal EAP enablement, ensuring Sales, Client Success, and Account Management teams are equipped to confidently position, support, and troubleshoot EAP offerings.
• Act as a primary escalation point for employer-facing EAP questions and issues.

Senior Manager, EAP Strategy – Operations

People Operations

• Serve as a trusted strategic advisor to executive and senior leaders across Commercial Go-To-Market, Marketing, and Care organizations, influencing decisions through data, insight, and high emotional intelligence
• Partner with leaders to translate business strategy into people strategy, driving organizational design, workforce planning, and talent optimization across salaried and hourly populations
• Lead complex change initiatives including scaling teams, new go-to-market motions, compensation model evolution, and care delivery transformations
• Champion Headspace values, diversity, equity, inclusion, and belonging in all people practices and leader interactions
• Drive performance management, succession planning, and leadership development strategies to build strong leadership benches and high-performing teams
• Advise and coach leaders on employee relations, performance challenges, and organizational health with sound judgment and a solutions-oriented mindset
• Partner closely with Total Rewards on sales compensation design, incentive effectiveness, and equitable pay practices
• Support teams with diverse operating models, including revenue-generating sales teams, creative and brand-driven marketing functions, and clinical/mental health provider populations
• Leverage business insights, data, analytics, and AI-powered tools to improve operational effectiveness, scale impact, scalability, proactive decision-making and deliver proactive people insights
• Collaborate closely with cross-functional People teams to deliver cohesive, high-impact solutions

People Business Partner

• Drive implementation of Avalara indirect tax engine to ensure accuracy and efficiency of indirect tax collection and remittance
• Oversee all global tax compliance and reporting, including federal, state, local, and international tax filings, as well as the preparation of the income tax provision and related disclosures in accordance with ASC 740
• Manage any tax audits, notices and enquiries received from domestic and foreign tax authorities
• Design, develop, and implement global tax planning strategies to minimize tax expense and exposure across federal, state, and foreign direct and indirect taxes, including evaluating sales tax obligations by state and monitoring legislative changes that impact tax positions and accounting implications
• Actively manage relationships with third party tax advisors to optimize the relationships to efficiently balance in house vs outsourced tax support
• Prepare and present clear, decision-oriented tax updates to executive leadership, including key risks, opportunities, and strategic tradeoffs
• Establish deep business partner relationships across the organization to ensure company strategy and projects include a thorough review of tax consequences
• Lead all significant tax initiatives, including M&A due diligence, new product launches, geographic expansion, and related tax studies
• Ensure compliance with global transfer pricing requirements
• Ensure appropriate internal controls related to tax matters are in place and operating correctly, identify any gaps in internal controls and ensure remediation and formalization of tax policies and procedures
• Establish and maintain formal tax policies, practices and procedures to ensure compliance with US GAAP and tax regulations.
• Build, mentor, and develop internal tax talent over time, including assessing future hiring needs as the company scales
• Own tax risk assessment, uncertain tax positions, and related documentation, including coordination of technical analyses and reserve positions under ASC 740