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Director, Customer Experience & Scaled Success

Hybrid - Boston, MA

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 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 expected to fall within the range of [$115,500-$214,500], depending on experience, skills, qualifications, and location. Offers are determined based on these factors as well as internal peer equity. It’s most common for new hires to start near the midpoint of the range, allowing room for growth as employees develop in their role. 

In addition to base pay, we offer a comprehensive total rewards package that supports both your wellbeing and professional growth, including:
  • Equity grants for all employees
  • A 4% matching 401(k) program
  • Medical, dental, vision, disability, and life insurance coverage for employees working 30+ hours per week
  • Monthly wellness stipend
  • Paid parental leave
  • A flexible vacation policy - we all work hard and take time when we need it
Who We Are:
At Hi Marley, our culture is built on three core values that every employee embodies:
  • Max Courage – We encourage our team, our customers, and their customers to dream big, try new ideas, and maximize impact by measuring risk.
  • Be Humble – We lead with appreciation and promote a culture of humility, compassion, and openness to learn from anyone, anywhere.
  • Ubuntu (“I am because we are”) – We believe true success is much bigger than any single individual or company. By aligning our individual aims behind a shared purpose, we can achieve our fullest potential — together.
Life at Hi Marley:
Life at Hi Marley is shaped by collaboration, learning, and genuine connection. We’re proud to foster an environment where people can do their best work, feel supported, and grow alongside a team that celebrates both individuality and shared purpose.
  • A fun, lively startup culture that embraces creativity and innovation
  • Core values-based leadership that guides our decision-making and daily interactions
  • A culture of engagement, diversity, inclusion, and belonging — everyone’s voice matters
  • Flexible, hybrid work environment that values balance and trust
  • Ample opportunities to learn, take on new challenges, and make an impact in a fast-growing organization
  • Meaningful work that directly supports our mission to help people and organizations communicate with empathy and clarity

Hi Marley is proud to be an equal employment opportunity employer. We celebrate diversity and do not discriminate based on gender, sexual orientation, gender identity, religion, race, veteran status, disability status, or any other characteristic protected by applicable law. We are committed to building an inclusive work environment representing a variety of backgrounds, perspectives, and skills, where all employees are encouraged to be their authentic selves.

Hi Marley participates in E-Verify and will provide the federal government with your Form I-9 information to confirm that you are authorized to work in the U.S. For more information, please review the documents under "E-Verify Poster" here: https://e-verify.uscis.gov/web/OnlineResources.aspx

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