Director Insurance Operations Jobs in Massachusetts

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.