HealthJoy

• Collaborate on architectural decisions and design best practices • Design and implement new features into the HealthJoy platform • Collaborate with engineering and product team members to improve quality and velocity • Creating a scalable solution to serve our growing user base.

Role Description HealthJoy’s Customer Success Team is leading the charge at HealthJoy to deliver industry-leading outcomes to our customers, with the ultimate goal of driving customer retention and growth. As a Customer Success Manager, you’ll lead a designated book of business aligned to HealthJoy’s most strategic broker partners. This is a unique opportunity for a high-energy benefits industry professional who is passionate about delivering customer value, and excited to pivot to a dynamic, fast-paced environment. You will be a key driver of HealthJoy’s revenue goals through proactive account management, strategic expansion, and world-class retention efforts. - Strategic Book Management: Confidently and independently own key outcomes for your book of business, including product adoption, utilization, Net Dollar Retention (NDR), and overall customer health. - Full-Cycle Revenue Ownership: Lead the end-to-end renewal and expansion sales process. Identify, negotiate, and close upsell opportunities by aligning HealthJoy’s marketplace solutions with customer needs. - Sales Cycle Execution: Demonstrate mastery of the full sales cycle within your book of business. Partner with Product Solutions Consultants and other senior leaders to conduct deep discovery to uncover pain points, map those challenges to HealthJoy solutions, and move deals forward by confidently asking for the close and defining clear, actionable next steps. - Executive Presence: Build strong, consultative relationships across all levels of a customer organization—from day-to-day champions to C-Suite stakeholders. Comfortable having direct, high-stakes conversations to drive alignment and value. - Crisis Management & Poise: Act as the primary external point of contact for escalations. Remain poised under pressure, resolving complex issues with a sense of urgency and a calm, solution-oriented mindset. - Strategic Advisement: Serve as main point of contact for your customers on strategies to optimize adoption across their members, drawing upon your extensive knowledge of HealthJoy’s product and services, benefit industry domain knowledge, and best practices. - Data-Driven Leadership: Leverage AI (Claude, Gemini) and best-in-class software to proactively dive deep into the performance across your book of business. - Meticulous Execution: Maintain a high level of attention to detail regarding customer contracts, health scores, and stakeholder updates, ensuring no risk goes unnoticed. - On-the-Road Partnership: Travel to meet with customers and their brokers throughout the year to conduct business reviews, deepen relationships, and solidify HealthJoy’s position as a long-term strategic partner. Qualifications - Benefits experience required. Experience working in benefits technology, health insurance or wellness technology is a great background for this role! - Minimum 4-5 years of customer-facing account leadership or related experience demonstrating a high degree of skill in serving as a trusted advisor. - Strategic and results-oriented approach to partnering with customers at all levels of an organization (individual contributor through C-Suite) to achieve desired outcomes. - Demonstrated success managing customer retention and account growth within a book of business. - Commercial Acumen: Proven ability to navigate a sales process, including overcoming objections, managing procurement/legal hurdles, and a "hunter" mindset for identifying expansion opportunities. - Highly collaborative and influential with your teammates and business partners across the organization to drive results and innovation. - Exceptional executive presence and ability to present complex or detailed information in a digestible and actionable manner. - Willingness to travel approximately 15-20% to support client book of business, as well as at a minimum quarterly to Chicago headquarters for internal team meetings. Benefits - Medical, Dental and vision insurance packages - HSA contribution match - Stock options for eligible roles - 401k match - Paid parental leave - Company sponsored Short Term and Long Term Disability coverage - Flexible PTO

• Confidently and independently lead a mid-market book of business. • Confidently and independently own key customer outcomes (product adoption and utilization, net dollar retention, and customer health) for clients within your book of business; • Build strong, consultative relationships with your customers and partners (champion to buyer); • Advise your customers on strategies to optimize adoption across their members, drawing upon your extensive knowledge of HealthJoy’s product and services, benefit industry domain knowledge, and best practices; • By conducting effective ongoing discovery about your customers and their wants and needs, uncover potential upsell and/or other account expansion opportunities, and partner effectively with HealthJoy’s Product Solution Consultant team to effectively position marketplace solutions and ultimately expand account value; • Lead the expansion sales and renewal process for customers within your book of business; • Use your deep understanding of HealthJoy’s value proposition and ROI to position HealthJoy’s value in customer business reviews; • Use best-in-class CRM software and business intelligence tools (Gong, Looker, Gainsight, and others) to proactively dive deep into the performance across your book of business, enabling you not only to provide better thought leadership to your book of business, but also socialize the voice of your customers across internal HealthJoy stakeholders. • Regularly provide product education to your customers, as new features and functionality are released to ensure ongoing awareness and adoption. • Customer relationship management is critical in this role as you are keenly aware of pertinent customer updates with regards to key stakeholders, company level changes, and raising awareness before risk to customer health arises. • You are able to work cross-functionally and pull in HealthJoy team members to support you when needed. You are the voice of the customer and act as an advocate for our customers, while providing feedback to relevant internal stakeholders. • Add value across the organization as a peer leader and senior-level contributor. • Contribute to cross-functional initiatives to improve team process, customer experience, and the attainment of revenue and customer health outcomes; • Support overall Customer Success team performance, in partnership with people managers, by developing internal domain-area training, templates, and other tools used by CSMs to improve the team’s overall understanding of the tools to success as a mid-market CSM; • Evangelize customer value across internal cross-functional teams, advocating for not only what HealthJoy’s customers need in order to be successful today but also in the future given benefit industry trends; • Keep an active pulse on the emerging needs of our mid-market customers and ensure HealthJoy is adapting future strategy and infrastructure to support the success of these clients; • Serve as a mentor to more junior team members looking to grow their careers in customer success and employee benefits.

Role Description You'll own Customer Success and the retention number that comes with it. That means two things at once: protecting and expanding revenue across our employer client base, and leading the team that owns those relationships through a genuine shift in how the work gets done. This is a commercial role, not a satisfaction role. Net revenue retention, gross retention, and expansion are the outcomes that matter. You own the renewal calendar, the churn-risk triage, the upsell and product-adoption motion, and the health of every client relationship from launch through renewal. You manage the function out of Salesforce, you know your book cold, and you can tell anyone in the company exactly where retention is being made or lost and why. It's also a building role, and increasingly an AI-native one. You'll lead a team and a roadmap that's moving toward a fully agentic customer lifecycle: specialized agents mapped to each phase of the client journey, triggered by real-time signals, orchestrated for the right message at the right moment. You don't have to have personally built that before, but you have to be genuinely excited to lead an organization that operates this way and to roll up your sleeves in the work. This role works cross-functionally with Sales, the Broker Partnership team, Marketing, RevOps, Data, Product, and Legal. Retention is a team sport here, and you'll be at the center of it. What You'll Do - Own net revenue retention and gross retention. - Drive expansion and product adoption. - Lead the AI-native transformation of Customer Success. - Run the team out of Salesforce. - Own the broker-advocacy dimension of retention. - Be the senior voice for clients. - Lead and develop the team. - Bring the numbers to the table. Qualifications - 8+ years in Customer Success, account management, or a commercial retention role, including team leadership. - Revenue-first mindset. - AI-native, or hungry to be. - Commercial and cross-functional fluency. - Comfort with data and systems. - Comfort with ambiguity. - Executive presence and clarity. - Healthcare or benefits experience preferred. Requirements - If you're looking for a defined playbook and a steady-state book of business to manage, this isn't it. - If your best work comes from relationship maintenance without a retention or expansion target, look elsewhere. - If AI feels like a threat or a distraction rather than the most exciting lever you have, the direction here will frustrate you. - If you need full certainty before acting, or a manager telling you exactly what to do next, you won't succeed. Reporting & Team This role reports to the Chief Growth Officer and leads the Customer Success organization, a team of experienced CS managers and their CSMs. You'll work closely with Sales, the broker partnership team, Marketing, RevOps, Data, Product, and Legal, and you'll have visibility into senior leadership as you shape the future of Customer Success at HealthJoy. Benefits - Medical, Dental, and Vision insurance packages - HSA contribution match - Stock options for eligible roles - 401k match - Paid parental leave - Company-sponsored Short Term and Long Term Disability coverage - Flexible PTO

• Own the accounting operations function and provide leadership on all accounting initiatives. • Responsible for the monthly and annual close process. • Manage relationships with all third-party vendors. • Coordinate all tasks within company audits. • Drive process improvements and contribute to accounting transformation. • Own the monthly and year-end close processes. • Ensure that financial records & reports are maintained in compliance with company policies & GAAP. • Analyze monthly operating results. • Oversee all payroll and billing functions. • Manage client invoicing and collections. • Lead the annual financial audit with independent CPA firm. • Coordinate the preparation of annual tax returns with independent CPA firm. • Ensure compliance with sales tax requirements. • Implement, document and maintain adequate and effective internal controls, policies, and procedures. • Provide leadership to the accounting staff.

• Own HealthJoy's Core Financial Models End-to-End: Take full ownership of the operating model, long-range plan, and the financial backbone of board reporting. You build, maintain, defend, and evolve; leadership reviews. Set the modeling standards the rest of the organization relies on. • Drive Strategic Finance Analyses That Move the Business: Lead the analytical work behind unit economics, segment profitability, pricing strategy, packaging, and growth analysis. Translate complex data into clear recommendations that executives can act on. • Sharpen GTM Performance Through Analytical Partnership with RevOps: Own the analytical layer for sales and marketing performance — pipeline economics, rep productivity, CAC efficiency, funnel diagnostics, channel ROI, comp plan economics. This is a meaningful portion of the role, not a side project; you'll partner closely with our GTM Systems lead to ensure the data is right and the insights are actionable. • Partner on the FP&A Operating Rhythm: Contribute to the monthly close partnership, budget vs. actuals reporting, headcount tracking, and the board financial package, working alongside other Finance team members who own pieces of this work. Serve as a finance partner for one or more departments, running their budget and headcount planning independently. • Triage and Structure Pricing and Deal Desk Work: Tee up non-standard deal requests with clean analysis and a recommended structure so decisions can happen faster. Serve as backup for routine pricing exceptions and escalate the hard ones with context. • Build AI-Native Finance Workflows: Be hands-on in shaping our AI-native finance function — designing workflows in Claude and other platforms, automating analysis and reporting, and creating finance tooling that didn't exist before. You should bring building appetite and aptitude; we'll build a lot together.

• Positioning governance — Maintain our positioning framework as the source of truth: what we say, what we don't say, how we differ from competitors, and where we don't play. Evolve it as the market and product change. • Narrative consistency — Evaluate marketing materials, sales content, and launch assets for messaging alignment. Partner with Content Marketing to keep the HealthJoy Benefits OS story coherent across every audience and channel. • GTM strategy & launch execution — Own positioning, messaging, and GTM strategy for product launches. Partner with Growth Marketing to translate product positioning into high-performing campaign themes and channel strategies. Lead cross-functional planning timed to industry seasonality and measure launch impact on the funnel. You are able to confidently work across teams and influence stakeholders and decision makers. • Market & competitive intelligence — Track market trends and how competitors position themselves. Maintain battlecards and oversee win/loss analysis. Keep a running record of what competitors say so we know what to avoid and where to counter. • Buyer expertise — Own deep knowledge of our buyers: benefits consultants, brokers, and the HR and finance leaders they advise at self-funded employers. Know their language and their pressures. • Product partnership — Work closely with Product Management. Understand the Benefits OS platform and its core capabilities well enough to position them confidently • Field team enablement — Partner with Revenue Enablement to build training and key message frameworks for Sales and Customer Success. Review training content for accuracy. Make sure field teams know what to say, what not to say, and why. • Performance & iteration — Tie PMM work to outcomes: win rate, sales cycle, content adoption. Work with Growth Marketing to analyze messaging resonance across digital channels. Use A/B test results and conversion data to refine our positioning and GTM activity.

Role Description The Vice President, Sales in our Western region will lead the team in driving strategic vision and revenue growth. The role involves: - Building and managing a high-performing sales team. - Collaborating with cross-functional teams. - Developing sales strategies aligned with market demands and customer needs. - Engaging directly in key deals while guiding the team in a “player/coach” capacity. Key responsibilities include: - Achieving team-based revenue growth targets in your region. - Partnering with sales leaders to develop strategy and go-to-market initiatives that maximize revenue. - Providing training and feedback to direct reports to improve their sales acumen. - Working to saturate the client portfolio with current broker relationships. - Developing new broker relationships to expand our distribution footprint. - Assisting in the delivery of product demonstrations and customer pitches. - Selecting, hiring, counseling/coaching, motivating, and developing new and current sales team members. - Supervising and managing a sales team to meet monthly goals. - Providing accurate reporting on sales activity and forecasting to senior sales management. - Exhibiting strong tenacity and a proactive mindset. - Possessing strong sales discovery skills. - Demonstrating executive presence with exceptional presentation and communication skills. - Engaging in social settings and showcasing adaptability. - Articulating the HealthJoy cost-containment value proposition. - Working in partnership within Sales, Marketing, Customer Success, Product, and Sales Enablement. - Demonstrating a deep understanding of the HealthJoy product offerings. - Fostering productive collaboration across various organizational levels. - Using Salesforce for deal tracking, forecasting, and performance management. - Able to learn the complexities of the healthcare, benefits, and navigation industries. Qualifications - Minimum of 5-7+ years experience in a leadership role managing senior sales professionals. - Minimum of 10 years of related field sales experience selling directly into benefits brokers/consultants. - Proven track record leading layered sales organizations focused on Mid-Market / Enterprise deals. - Familiarity with channel-based sales approach. - Owned a revenue target with accurate forecasting and disciplined pipeline management. - Strong analytical approach using data to run your team. - Experience building or scaling sales processes in a growth-stage environment. - Ability to travel 50% of the time. Requirements - Demonstrated sales leadership experience and accountability for team growth targets. - Strong analytical skills and data-driven decision-making. - Ability to articulate and run demos using HealthJoy technology. Benefits - Medical, Dental, and vision insurance packages. - HSA contribution match. - Stock options for eligible roles. - 401k match. - Paid parental leave. - Company-sponsored Short Term and Long Term Disability coverage. - Flexible PTO.

• Process member requests (tickets) • Search for appropriate doctors, clinics, healthcare facilities • Interact with members via telephone and chat for assistance • Collaborate with leadership and staff for support strategies • Provide a WOW experience and care to HealthJoy’s American customer base

• Real-Time Design Judgment. • Design Inside the System. • AI Interaction Design. • Cognitive Load and Perception. • Near-Term Vision Setting. • System Coherence. • Field Signal Collection.