Director, Customer Deployment & Delivery

Hi Marley Inc; Boston (MA); Hybrid; USD 109,000 - 202,000; Full time

Benefits offered by this job

Equity grants for all employees

4% matching 401(k)

Medical, dental, vision, disability, &

Life insurance coverage

Monthly wellness stipend

Paid parental leave

Flexible vacation policy

Job summary

Hi Marley is seeking a strategic Director to lead the Customer Deployment & Delivery organization, responsible for implementation, integrations, onboarding, adoption, and successful launches across the product portfolio.

This role partners with Product, Engineering, and Customer Success to ensure meaningful business outcomes, with a focus on scalable methodologies and delivering value in a hybrid Boston-based environment.

Qualifications

• 10+ years leading enterprise SaaS implementation, professional services, customer deployment, consulting, or customer transformation teams.
• 5+ years of people leadership, building and growing high-performing teams.
• Experience in the P&C insurance industry and understanding of insurance operations and customer experience challenges.
• Proven success guiding complex deployments and driving measurable outcomes in a B2B software environment.
• Strong consultative leadership, with ability to influence executive stakeholders.
• Experience designing, improving, and scaling delivery processes or service models.
• Demonstrated ability to partner across Product, Engineering, Sales, Customer Success, and Support teams.
• Experience leading multidisciplinary teams combining implementation, integration, consulting, and delivery.
• Strong business acumen and executive communication skills.
• Ability to operate in ambiguity and drive progress in unclear environments.
• Intellectual curiosity about AI and emerging technologies with responsible application.

Responsibilities

• Lead and develop a high-performing Customer Deployment & Delivery organization for implementation, integrations, onboarding, adoption readiness, and successful launches.
• Ensure customers achieve meaningful outcomes while preserving trusted-partner experience.
• Build relationships with customer stakeholders as strategic advisors to maximize value at the start.
• Drive excellence in delivery from kickoff through transition to Customer Success with high-quality outcomes.
• Improve deployment methodologies, processes, playbooks, and tools for scalability and speed-to-value.
• Design delivery approaches based on customer segment, product complexity, and objectives.
• Establish and monitor KPIs for deployment quality, outcomes, adoption, and efficiency.
• Partner with Product, Engineering, Customer Success, Support, Sales to ensure seamless experiences.
• Identify opportunities to leverage automation and AI capabilities to improve outcomes.
• Shape deployment and services model as product portfolio expands.

Skills

Enterprise SaaS leadership

People leadership

Executive stakeholder engagement

Cross-functional collaboration

Strategic advisory

Operational excellence

AI awareness

Delivery leadership

Change management

Communication with C-suite

Job description

Director, Customer Deployment & Delivery

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 area 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.

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".