Sr. Director/VP, Customer Success & Marketing

About FlyteHealth FlyteHealth is a cardio-kidney-metabolic care provider transforming how obesity, prediabetes, hypertension, and hyperlipidemia are treated. Our model combines behavioral lifestyle change, virtual clinical care, remote monitoring, and a multidisciplinary care team. We partner with employers, payors and PBMs, health systems, consultants, and care navigators to expand access and deliver measurable outcomes. The opportunity We are seeking a hands–on leader to own and scale FlyteHealth's Customer Success and Marketing functions. You will help employers, payors, PBMs, and other partners realize measurable value, strengthen retention and growth, and build the marketing engine that brings our story to market and drives member enrollment. Reporting to the CEO, this leader will set strategy, lead the team and vendors, and personally manage key relationships and initiatives. You will own client success and marketing strategy, execution, and budget, partnering with Sales and Business Development, Clinical Operations, Product, Data, Finance, and Compliance. What you will own Own the client lifecycle, retention, and growth Own the client journey from sales handoff and implementation through adoption, ongoing performance, renewal, and expansion; create a consistent experience and clear accountability at every stage. Build trusted relationships with executive sponsors and day-to-day stakeholders at employers, payors, PBMs, and other partners; serve as the senior point of accountability for client value and issue resolution. Create client success plans with shared objectives, launch milestones, engagement goals, governance, and escalation paths; coordinate operational readiness, reporting, and commitments across internal teams. Lead regular business reviews that translate validated clinical, engagement, and economic results into a clear value story; identify risks early, agree on corrective actions, and track commitments through completion. Own retention and renewal readiness, and lead expansion within existing accounts in partnership with Sales and Business Development; build account plans, surface new opportunities, and develop client advocates. Drive member enrollment and engagement Build client‑specific launch and enrollment campaigns across email, digital channels, employer and benefits communications, webinars, and partner toolkits; make it easy for eligible members to understand and access FlyteHealth. Partner with Clinical Operations and Product to improve the journey from awareness and enrollment to activation and sustained engagement; test messaging and outreach, remove barriers, and track conversion at each stage. Establish feedback loops with clients, members, and frontline teams; lead client escalations, address root causes, and translate recurring needs into better communications, workflows, and product priorities. Create repeatable launch and engagement playbooks for new clients, partners, and channels, with clear ownership across implementation, data, operations, training, and member communications. Own Marketing strategy and Execution Set FlyteHealth's marketing strategy, brand positioning, and messaging for employers, payors, PBMs, consultants, and members; translate our care model and validated outcomes into a clear, consistent market story. Lead demand generation and sales enablement across content, thought leadership, website, email, social, events, and partner campaigns; equip the commercial team with compelling collateral, presentations, and proposal materials. Own the marketing budget, calendar, channel mix, creative resources, and agency relationships; use disciplined testing, segmentation, and attribution to improve qualified pipeline, conversion, and return on spend. Develop client case studies, testimonials, and advocacy programs that support acquisition and renewal; partner with Clinical and Compliance on accurate claims, appropriate permissions, and responsible use of client and member information. Build the team and operating system Build and lead the Customer Success and Marketing team, including external partners; set priorities, clarify roles, coach performance, and balance capacity and investment across both functions. Establish a shared dashboard and review cadence for client health, retention, renewals, expansion, enrollment, activation, engagement, satisfaction, marketing‑sourced pipeline, conversion, and campaign performance. Create scalable processes across CRM, marketing automation, account planning, campaign execution, and reporting; improve data quality, documentation, handoffs, and the reliability of client‑facing deliverables. Bring the voice of the client and market to the CEO and leadership team; use insights to inform growth strategy, product priorities, resource allocation, revenue forecasting, and new opportunities. What success looks like Diagnose and prioritize. Within 90 days, assess the client portfolio, renewal outlook, member journey, marketing performance, team capabilities, and tools; establish baselines and a prioritized plan for both functions. Build a disciplined client‑success model. Establish success plans, launch playbooks, client health reporting, and business reviews; improve retention, renewal readiness, expansion opportunities, and client confidence. Connect marketing to measurable growth. Deliver consistent positioning, a practical campaign plan, and clear funnel reporting; improve qualified pipeline, member enrollment, activation, and campaign effectiveness against agreed baselines. Strengthen and scale. Build a capable team and a repeatable operating model that supports growth, demonstrates client value, and turns satisfied clients into advocates. What we are looking for: Required experience and capabilities 7+ years of progressive experience in customer success, strategic account management, marketing, or commercial leadership, including 3+ years leading a team, function, or major initiative. Demonstrated ownership of B2B client implementations, executive relationships, retention, renewals, and account growth, preferably in digital health, healthcare services, or employee benefits. Direct ownership of marketing strategy and execution, with evidence of improving positioning, demand generation, lifecycle campaigns, sales enablement, and measurable commercial results. A record of building or materially scaling a customer success or marketing function in a startup, growth‑stage company, or similarly fast‑changing organization; comfort operating across both disciplines. Strong analytical and commercial judgment, including the ability to interpret engagement, clinical, and economic reporting, assess client health, and translate results into a credible value story. Excellent executive communication, writing, and relationship skills; the ability to align clients and internal teams, manage escalations, and explain complex healthcare offerings clearly. Practical fluency with CRM, marketing automation, and analytics tools, plus experience managing teams, vendors, budgets, campaign performance, and operating priorities. Especially valuable Experience serving employers, health plans, PBMs, benefits consultants, brokers, or healthcare distribution partners, with an understanding of their buying processes and success measures. Experience with virtual care, chronic‑condition management, cardio‑kidney‑metabolic health, or another healthcare offering where engagement and outcomes drive client value. Experience leading both customer success and marketing, or building member enrollment and lifecycle programs alongside responsibility for client retention and growth. How you operate You are a builder and owner, comfortable moving between strategy, operating detail, client relationships, and hands‑on campaign execution. You create clarity in ambiguity, set practical priorities, align cross‑functional teams, make sound decisions with imperfect information, and close loops. You combine empathy, commercial judgment, and analytical rigor; you communicate plainly, follow through, and balance client value, member experience, growth, and responsible healthcare marketing. FlyteHealth Bene fi ts: Comprehensive health, dental and vision insurance 401(k) Discretionary PTO Plan Parental leave FlyteHealth Perks: Flexible working hours Remote‑first Company Internet Stipend for remote working Paid Company Holidays FlyteHealth values diversity and is committed to equal opportunity for all persons regardless of their race, religion, color, creed, marital status, age, national origin or ancestry, physical disability, medical condition, sexual orientation, and gender identity. #J-18808-Ljbffr 25madison LLC