Director, Customer Experience & Scaled Success

Insurance touches people during some of the most challenging moments in their lives. Hi Marley is on a mission to transform how the P&C industry communicates, making those moments faster, easier, and more empathetic for carriers and the customers they serve. We build AI-powered software that keeps everyone in the claims conversation informed and connected. If you believe insurance can combine operational excellence and automation with a human touch, we’d love to meet you. Director, Customer Experience & Scaled Success We are looking for a Scaled Success / Customer Experience Leader to define and evolve how Hi Marley engages customers at scale. This is leadership role responsible for building the programs, journeys, and engagement systems that help customers successfully adopt our products, realize value quickly, and deepen their partnership with Hi Marley over time. You will own the strategy and architecture of our scaled engagement model: the onboarding and adoption journeys, customer forums, advocacy initiatives, and community experiences that drive engagement, retention, and long-term customer success across our customer base. You will help define how customers move from initial deployment to confident, habitual usage - and ultimately into advocates who influence our product and champion our brand. This role is ideal for a builder who thrives at the intersection of customer experience, lifecycle design, behavioral engagement, and operational scale - someone energized by turning ambiguity into repeatable systems that improve both customer outcomes and team leverage. If you’re energized by building, motivated by impact, and excited to shape the future of learning and enablement in a company that’s scaling quickly and thoughtfully, we’d love to meet you. Teamwork and shared enthusiasm is a core part of our culture, which is why this role involves joining us in the Boston office for 2-3 days each week. What You’ll Do: Build scalable onboarding and adoption journeys that create more consistent customer experiences Reduce operational and coordination burden on Customer Success Managers through repeatable programs, workflows, and engagement systems Design automated and semi-automated engagement motions using lifecycle, behavioral, and product usage signals Identify customer friction points, adoption gaps, and engagement drop-offs, and design interventions to improve outcomes at scale Design and evolve customer programs including webinars, forums, community initiatives, advocacy, and executive engagement experiences Drive experimentation and continuous optimization of journeys and programs Define and own metrics and performance outcomes (adoption, engagement, NRR, customer health) Partner cross-functionally with Customer Ops, Learning & Enablement, Marketing, Product, and Customer Success to deliver cohesive and valuable experiences What We’re Looking For: 8-10+ years in Customer Success, Customer Experience, Lifecycle Programs, Community, or related B2B SaaS roles Experience building scalable customer engagement systems, beyond managing campaigns Proven ability to operationalize repeatable customer motions in growing organizations Strong understanding of customer journey design, adoption systems, and behavioral engagement Experience reducing operational complexity and improving leverage for customer-facing teams Data-driven mindset with the ability to use behavioral and engagement signals to improve outcomes Comfort operating in ambiguity and building systems from scratch Strong cross-functional collaboration skills Curiosity about AI-enabled workflows and how customers adopt new operational behaviors Builder mentality: pragmatic, iterative, and execution-oriented A genuine curiosity about AI and emerging technologies, paired with the judgment to apply them thoughtfully and responsibly Compensation, Benefits & Perks: At Hi Marley, we are committed to fair and transparent pay practices. The annual base salary for this role is expec