• Unify TechOps Organizations: Consolidate the infrastructure teams across acquired entities into a single global function with consistent processes, tooling, titles, and culture. • Drive Cultural Transformation: Instill a culture of urgency, ownership, and a bias toward action across all infrastructure teams globally, embracing AI-powered agentic workflows to accelerate velocity. • Design Organizational Structure: Implement a structure that streamlines operations and optimizes for velocity, eliminating redundancies and establishing clear ownership, accountability, and escalation paths across approximately 150 employees. • Build Talent Pipeline: Drive workforce planning, skills development, and talent acquisition to ensure the organization has the capabilities required for a modern, cloud-forward infrastructure environment. • Own Core Infrastructure: Operate and optimize on-premises and cloud data centers, networking, server and container virtualization, operating systems, databases, and L3 customer system support. • Drive Cloud Modernization: Lead cloud migration and modernization initiatives, optimizing the balance between on-premises and cloud infrastructure for cost, performance, and reliability. • Establish Operational Excellence: Define and enforce SLAs, incident management, disaster recovery, and business continuity standards across the entire infrastructure estate. • Implement Observability & Automation: Deploy robust monitoring, observability, and automation to improve system reliability and reduce mean time to resolution. • Manage End-User Technology: Oversee employee hardware lifecycle management, productivity software deployment, and L2 internal user support across a global workforce. • Champion AI Adoption: Drive enterprise-wide adoption of AI-powered tools and agentic workflows across the infrastructure organization, creating a culture of velocity through intelligent automation. • Optimize Enterprise Platforms: Manage and optimize the enterprise systems portfolio including NetSuite (Finance), Coupa (Procurement), Workday (HR), and Salesforce (Sales), ensuring alignment with business processes and organizational needs. • Partner with Business Leaders: Collaborate with Finance, Procurement, HR, and Sales leadership to translate operational requirements into system capabilities and drive adoption. • Manage Vendor Relationships: Oversee vendor relationships, contract negotiations, and total cost of ownership for enterprise platforms. • Establish a rigorous quarterly planning process with strong commitment to frequent, predictable releases across all infrastructure services. • Provide real-time visibility to the executive team and organization on work in progress, scheduled release dates, and capacity mapped to strategic initiatives.

• Lead a dynamic team transforming how retailers operate • Oversee District Sales Managers and Territory Account Executives • Drive performance against key goals: unit sales, revenue, employee engagement, and customer satisfaction • Responsible for hiring, onboarding, and continuously developing the sales team • Collaborate with Sales, Product, and Finance to align retail marketing strategies with revenue goals • Build the operating model, analytics capabilities, and data infrastructure • Champion best practices in multi-channel marketing • Partner as a core member of the Retail Leadership Team to architect unified go-to-market programs

Join us in creating a better way! At eHealth, our mission is to expertly guide consumers through their health insurance and related options when, where, and how they prefer. We’re creating a better way – one that’s transparent and trustworthy for both our consumers externally and our employees internally. Move your career forward while connecting countless people to the life- changing, quality care they deserve. Our diverse team of innovators supports one another in solving some of the toughest challenges. We’re always on the lookout for creative opportunities to do right by our customers, and each other. Together, we’re creating a better way to work, united by our common passion to make a difference. Company Overview: eHealth is a leading health insurance marketplace connecting millions of consumers to affordable, high-quality coverage. Through partnerships with 180 carriers nationwide, we offer Medicare Advantage, Medicare Supplement, and Part D prescription drug plans — along with individual, family, small business, and ancillary products. As part of our next phase of growth, we are transforming from a transactional enrollment platform into the #1 digital + telephonic Medicare marketplace to help seniors not only enroll in coverage, but save money, improve access to care, better use their benefits and navigate healthcare year-round. We are seeking a bold, data-driven executive to serve as Vice President, Marketing & General Manager of Medicare to lead this transformation. Role Overview: As the Vice President & General Manager of the Medicare Business Unit, you will work closely with executive leadership and are responsible for growth strategies, performance, profitability and long-term value creation of the Medicare business. Reporting to the Chief Revenue Officer, the VP will: - Lead integrated, omni-channel marketing orchestration and optimization - Champion a seamless consumer experience across digital and telephonic journeys - Expand high-margin marketplace services through strategic partnerships You will lead a cross-functional team to design, develop, and set operating goals, implement a roadmap of strategic initiatives, customer experience and marketing campaigns that deliver profitable growth, customer lifetime value (LTV) and retention. Key Responsibilities: General Management - Partner on building the forecast, and operating plan for the Medicare business unit - Aligns SLT and Medicare business unit behind the translation of corporate strategy into business unit strategy, connected to the forecast and growth roadmap priorities - Develop the business case for growth, investment and resource prioritization to deliver against the organization’s financial goals - Lead cross functional teams through resource prioritization and initiative progress - Regularly share business results, roadmap progress, any risks & opportunities with the Executive Leadership Team - Define outcome goals, KPIs, and performance dashboards - Deliver revenue growth, CAC efficiency, and LTV expansion - Conduct market research and competitor analysis to stay ahead of industry trends, regulatory changes, and customer needs - Drives investment and prioritization tradeoffs that maximize enterprise value - Represent the Medicare business in executive reviews and planning forums - Ensure operational readiness for new products, partnerships, and capabilities Marketing Orchestration & Performance Optimization Oversee paid media budget exceeding $100M, driving profitable customer acquisition and engagement across TV, Direct Mail, Social, SEM, email, partners and emerging channels. - Develop and execute a multi-year Medicare growth strategy - Optimize full-funnel performance across ecommerce and telesales - Leverage multi-touch attribution and marketing mix modeling - Improve CAC while increasing lead quality and sales conversion - Lead segmentation strategies across key Medicare audiences - Build differentiated brand and creative platforms - Oversee agency and vendor performance to ensure ROI and alignment - Drive a culture of experimentation, testing, and data-driven optimization - Ensure compliance with healthcare regulations and guidelines. Consumer Experience Leadership Marketing connected to a seamless customer experience builds trust and drives retention; ensure alignment across the full Medicare journey. - Represent the consumer & brand voice in product, service, and process design - Develop a deep understanding of consumer personas and leverage insights to refine and align messaging, targeting strategies and customer experience. - Partner with Sales, Product, and Customer Care to reduce friction and increase conversion - Connect digital and advisor-led interactions for consistency - Develop lifecycle strategies that increase revenue and retention - Ensure compliance with CMS and healthcare regulatory standards Marketplace Expansion & Strategic Partnerships Beyond health plan enrollment, eHealth is expanding into services that solve meaningful senior needs while generating recurring, high-margin revenue. You will evaluate, prioritize, and scale marketplace opportunities such as: - Prescription drug savings and comparison tools - Medication management and adherence programs - OTC and Flex Card marketplace experiences - Benefit navigation and utilization tools - Supplemental insurance cross-sell - Transportation, DME, and chronic care support partnerships - Develop business cases, negotiate strategic partnerships, oversee integration into digital and telesales workflows, and ensure strong financial returns. Ideal Experience: - 15+ years of senior leadership experience in general management, marketing, or both - Ability to scale consumer businesses - Deep experience in performance marketing and ROI optimization - Healthcare or Medicare experience strongly preferred - Experience managing large paid media budgets ($100M+) - Strong financial acumen and operating plan management - Data-driven decision maker with strong analytical capabilities - Excellent leadership and team-building skills, with the ability to inspire and manage cross-functional teams to achieve business objectives. - Exceptional communication and storytelling skills, able to articulate complex concepts concisely to various stakeholders. - Strong project management skills, with the ability to juggle multiple priorities and ensure timely delivery across diverse teams and stakeholders. Who You Are: - Consumer Obsessed – Deep empathy for seniors and their healthcare challenges - Strategic & Analytical – Able to define the clearest path to value creation - Outcome-Driven GM – Owns results and makes disciplined tradeoffs - Growth Architect – Knows how to scale acquisition while expanding lifetime value - Clear Communicator & Influencer – Leads through insight, clarity, and credibility - Builder of High-Performance Teams – Develops talent and fosters accountability - Innovative & Agile - Thrive in an entrepreneurial environment, embracing change and staying ahead of market trends to drive continuous innovation. What we offer: - Generous benefits include medical, dental and vision beginning on your first day of employment - 401K with matching - Tuition reimbursement - Employee stock purchase program - 12 company paid holidays and flexible time off (PTO for non-exempt) Our Values: At eHealth, our core values guide our work: - One Team - Customer Centric - Innovation - Integrity - Quality - Accountability - Relentless - Financial Stewardship *Please note the above is a summary of responsibilities; a full job description is available upon request. Job Application Deadline: April 13 #LI-Remote #LI-SG - The base pay range reflects the anticipated pay range for this position. The actual base pay offered will depend on various factors including individual skills, experience, performance, qualifications, the department budget, and the location where work is performed. Base pay is one component of eHealth’s total rewards package, which also includes an annual performance bonus, plus an array of benefits designed to support employees’ personal and professional wellness. For more information on our total rewards offerings, please visit our career site.- Base Pay Range -$214,200 - $285,600- eHealth is an Equal Employment Opportunity employer. It is our policy to provide equal opportunity to all employees and applicants and to prohibit any discrimination because of race, color, religion, sex, national origin, age, marital status, sexual orientation, genetic information, disability, protected veteran status, or any other consideration made unlawful by applicable federal, state or local laws. The foundation of these policies is our commitment to treat everyone fairly and equally and to have a bias-free work environment.

Toast Retail is our newest and most significant investment in the future of commerce. Launched in January 2025, Toast for Retail is poised to revolutionize the retail industry by providing an all-in-one operating system for retailers to manage every aspect of their business. Our initial focus is on landing key customers in the CPG space. Toast for Retail empowers these businesses to streamline operations, optimize inventory, enhance the customer experience, and ultimately drive growth. Role Overview As the RVP of Retail Field Sales you will lead a dynamic team that’s transforming how retailers operate. You’ll oversee a group of field-based District Sales Managers and Territory Account Executives across a defined region, driving performance against key goals including unit sales, revenue, employee engagement (eNPS), and customer satisfaction (cNPS). In this role, you’ll be responsible for hiring, onboarding, and continuously developing your team through coaching, support, and performance management—empowering each person to achieve and surpass growth. Beyond a deep understanding of omni-channel journeys, you bring a disciplined, data-first approach to demand generation and pipeline health, ensuring every marketing dollar is an optimized investment toward our aggressive retail growth targets. This leader will demonstrate excellence across three core competency areas, along with their associated capabilities: - Operational Excellence - Talent identification - Analytical skills - Tactical execution & process delivery - Financial deliverables - Problem solving, innovation and creativity - Strategic Thinking - Strategic vision and planning - Effective decision making and judgement - Overall business acumen - Continuous improvement cycling - Advanced Leadership - Coaching/Mentoring - Communication (written & verbal) - Interpersonal savvy - Building culture, morale and team motivation - Talent development A day in the life (Responsibilities) - Develop & lead a comprehensive Retail Marketing strategy that drives acquisition, engagement and revenue across retail customers - Ensure all retail marketing strategies are aligned with revenue goals, owning full-funnel performance and metrics from lead generation to conversion and retention in close partnership with Sales, Product and Finance - Build the operating model, analytics capabilities, measurement frameworks and data infrastructure to optimize funnel performance and confidently forecast demand and outcomes - Champion best practices in multi-channel marketing - including digital advertising, organic content, email, field/partner programs and local campaigns - to reach and convert retail business owners - Partner as a core member of the Retail Leadership Team to architect unified go-to-market programs; you will collaborate across the entire Retail ecosystem - from Product & Engineering to Sales & Customer Success - to ensure marketing strategies are seamlessly embedded throughout the merchant lifecycle - Partner with the core Marketing organization to leverage global scale across brand identity, joint funnels and shared data infrastructure; you will work cross-functionally to collaborate on performance marketing best practices that drive vertical efficiency and full-funnel optimization What you'll need to thrive (Requirements) - 5+ years of B2B technology sales leadership experience including at least 3 years directly leading managers of quota-carrying sales teams - Proven ability to operate effectively at both strategic and hands-on execution levels - Clear perspective on sales methodologies and their application in dynamic environments - Commitment to frontline enablement, with attention to detail and a passion for team success - Experience in building and scaling sales in emerging markets or with new product categories - Strong collaborator with a track record of fostering a results-driven, inclusive, and team-oriented culture Proficiency in sales funnel management and applying data to drive operational excellence - Background in the retail or point-of-sale (POS) industry is a plus AI at Toast At Toast, one of our company values is that we're hungry to build and learn. We believe learning new AI tools empowers us to build for our customers faster, more independently, and with higher quality. We provide these tools across all disciplines, from Engineering and Product to Sales and Support, and are inspired by how our Toasters are already driving real value with them. The people who thrive here are those who embrace changes that let us build more for our customers; it’s a core part of our culture. Our Total Rewards Philosophy We strive to provide competitive compensation and benefits programs that help to attract, retain, and motivate the best and brightest people in our industry. Our total rewards package goes beyond great earnings potential and provides the means to a healthy lifestyle with the flexibility to meet Toasters’ changing needs. Learn more about our benefits at https://careers.toasttab.com/toast-benefits. The estimated Total Targeted Cash compensation range for this role is listed below. Total Targeted Cash for this role includes base salary, commission, and bonus (if eligible). This role qualifies for uncapped commissions. The starting salary will be determined based on skills, experience, and geographic location. In addition to cash compensation, our total rewards components include benefits and equity (if eligible). Total Targeted Cash $271,000—$434,000 USD How Toast Uses AI in its Hiring Process Throughout the hiring process, our goal is to get to know you. We use AI tools to support our recruiters and interviewers with tasks like note-taking, summarization, and documentation of interviews to ensure they can be fully focused on your conversation. All hiring decisions are made by people. Diversity, Equity, and Inclusion is Baked into our Recipe for Success At Toast, our employees are our secret ingredient—when they thrive, we thrive. The restaurant industry is one of the most diverse, and we embrace that diversity with authenticity, inclusivity, respect, and humility. By embedding these principles into our culture and design, we create equitable opportunities for all and raise the bar in delivering exceptional experiences. We Thrive Together We embrace a hybrid work model that fosters in-person collaboration while valuing individual needs. Our goal is to build a strong culture of connection as we work together to empower the restaurant community. To learn more about how we work globally and regionally, check out: https://careers.toasttab.com/locations-toast. Apply today! Toast is committed to creating an accessible and inclusive hiring process. As part of this commitment, we strive to provide reasonable accommodations for persons with disabilities to enable them to access the hiring process. If you need an accommodation to access the job application or interview process, please contact candidateaccommodations@toasttab.com. ------ For roles in the United States, it is unlawful in Massachusetts to require or administer a lie detector test as a condition of employment or continued employment. An employer who violates this law shall be subject to criminal penalties and civil liability.