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.
Hi Marley is looking for a strategic and customer-obsessed Director to lead our Customer Deployment & Delivery organization. This leader will build on our reputation as a trusted partner while evolving how we deliver value to customers as our product portfolio expands and AI-powered solutions become an increasingly important part of the customer experience.
You will develop and lead a high-performing team responsible for implementation, integrations, and customer deployment, ensuring customers achieve meaningful business outcomes while helping shape the future of our delivery model. This is an opportunity for an operator and builder who is energized by scale, ambiguity, and the chance to influence how customer deployment evolves at a growing company. Teamwork and shared enthusiasm are 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:
- Lead and develop a high-performing Customer Deployment & Delivery organization responsible for implementation, integrations, onboarding, adoption readiness, and successful customer launches
- Ensure customers achieve meaningful business outcomes while preserving the trusted-partner experience that has become a hallmark of Hi Marley
- Build strong relationships with customer stakeholders, serving as a strategic advisor who helps customers successfully adopt new ways of working and maximize the value of their investment at the start
- Drive excellence in customer deployment outcomes from kickoff through transition to Customer Success, ensuring consistent execution, accountability, and high-quality delivery
- Continuously improve deployment methodologies, processes, playbooks, and tools to increase scalability, quality, predictability, and time-to-value
- Design and evolve delivery approaches based on customer segment, product complexity, and business objectives, balancing customer outcomes with efficient use of team capacity
- Establish and monitor key performance indicators that measure deployment quality, customer outcomes, adoption, team productivity, and operational effectiveness
- Partner closely with Product, Engineering, Customer Success, Support, Sales, and Learning & Enablement to create a seamless customer experience and ensure deployment insights influence product and business decisions
- Identify opportunities to leverage automation, technology, and emerging capabilities to improve customer outcomes, streamline delivery, and increase organizational leverage
- Help shape how Hi Marley evolves its deployment and services model as our product portfolio expands and AI-powered solutions become an increasingly important part of the customer experience
- Operate effectively in ambiguity, helping the organization evaluate, test, and refine new approaches to customer deployment, service delivery, and adoption
- Foster a culture of accountability, continuous improvement, customer obsession, innovation, and team development while building the next generation of leaders within the organization
What We’re Looking For:
- 10+ years of experience leading enterprise SaaS implementation, professional services, customer deployment, consulting, or customer transformation organizations.
- 5+ years of people leadership experience, including building, developing, and leading high-performing teams through growth and change.
- Experience in the P&C insurance industry and an understanding of insurance operations, workflows, and customer experience challenges.
- Proven success leading complex customer deployments and driving measurable business outcomes in a B2B software environment
- Strong consultative leadership skills, with the ability to build trusted relationships, guide customers through organizational change, and influence executive stakeholders
- Experience designing, improving, and scaling operational processes, delivery methodologies, or service models that improve customer outcomes and organizational effectiveness
- Demonstrated ability to partner effectively across Product, Engineering, Sales, Customer Success, Support, and other cross-functional teams
- Experience leading multidisciplinary teams that combine implementation, integration, consulting, and customer-facing delivery expertise
- Strong business acumen, executive presence, and communication skills, with the ability to engage both technical and business audiences
- Demonstrated ability to operate effectively in ambiguity, solve complex problems, and drive progress in environments where the answer is not always obvious
- Intellectual curiosity and a growth mindset, with enthusiasm for exploring how emerging technologies and evolving customer expectations can shape future customer experiences
- 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 [$109,000–$202,000], 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.
- 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
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.
- 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
Skills Required
- 10+ years leading enterprise SaaS implementation, professional services, customer deployment, consulting, or customer transformation organizations
- 5+ years of people leadership experience, including building and developing high-performing teams
- Experience in the P&C insurance industry with understanding of insurance operations and workflows
- Proven success leading complex customer deployments and driving measurable business outcomes in a B2B software environment
- Strong consultative leadership skills; ability to build trusted relationships and influence executive stakeholders
- Experience designing, improving, and scaling operational processes, delivery methodologies, or service models
- Demonstrated ability to partner effectively across Product, Engineering, Sales, Customer Success, Support, and Enablement
- Experience leading multidisciplinary teams that combine implementation, integration, consulting, and customer-facing delivery expertise
- Strong business acumen, executive presence, and communication skills to engage technical and business audiences
- Ability to operate effectively in ambiguity, solve complex problems, and drive progress
- Intellectual curiosity and growth mindset, with enthusiasm for emerging technologies and evolving customer expectations
- Genuine curiosity about AI and emerging technologies, with judgment to apply them thoughtfully and responsibly
- Willingness to work in the Boston office 2-3 days per week (hybrid)
What the Team is Saying
Hi Marley Compensation & Benefits Highlights
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Healthcare Strength — Day-one medical, dental, and vision coverage with HSA/FSA options and mental-health resources are highlighted. Materials also reference an EAP and wellness support that extend beyond basic insurance.
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Inclusive Benefits Coverage — Offerings explicitly include reimbursement for reproductive-health travel, coverage for assisted reproductive/infertility care, and support for gender-affirming services. Company materials make these inclusive benefits clear and accessible.
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Parental & Family Support — Paid parental leave, a post‑leave return‑to‑work program, and childcare/wellness reimbursements are emphasized. These policies aim to support family needs alongside work responsibilities.
Hi Marley Insights
What We Do
Hi Marley is the first intelligent conversational platform built for P&C insurance and powered by SMS. Designed by insurance professionals, Hi Marley enables lovable, convenient conversations across the entire ecosystem, saving money and time for carriers while building customer loyalty through delightful interactions. Hi Marley's industry-leading collaboration, coaching and analytics capabilities deliver crucial insights that streamline carrier operations while enabling a frictionless customer engagement experience. The solution is made for the enterprise; it’s fast to deploy, easy to use and seamlessly integrates with core insurance systems. Through its advanced conversational technology, Hi Marley reduces friction – empowering innovative carriers to reinvent the customer and employee experience.
Why Work With Us
Our team is made up of people who care about each other and are passionate about what we do in and outside of work. We promote a culture of continuous learning, always seeking ways to be better for ourselves, our team and our customers. Creativity is encouraged and valued throughout the company and is paramount to our innovation.
Gallery
Hi Marley Offices
Hybrid Workspace
Employees engage in a combination of remote and on-site work.
We thrive on teamwork and shared enthusiasm, which is why we are in the office for two days each week.
