HealthJoy

• 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.

• Confidently and independently own key outcomes for your book of business, including product adoption, utilization, Net Dollar Retention (NDR), and overall customer health. • Lead the end-to-end renewal and expansion sales process. You will identify, negotiate, and close upsell opportunities by aligning HealthJoy’s marketplace solutions with customer needs. • Demonstrate mastery of the full sales cycle within your book of business. You will 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. • Build strong, consultative relationships across all levels of a customer organization—from day-to-day champions to C-Suite stakeholders. You must be comfortable having direct, high-stakes conversations to drive alignment and value. • Act as the primary external point of contact for escalations. You remain poised under pressure, resolving complex issues with a sense of urgency and a calm, solution-oriented mindset. • 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; and partner effectively with HealthJoy’s Product Solution Consultant team to effectively position marketplace solutions and ultimately expand account value. • Leverage AI (Claude, Gemini) and best-in-class software 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. • Maintain a high level of attention to detail regarding customer contracts, health scores, and stakeholder updates, ensuring no risk goes unnoticed. • 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.