Technical Delivery Lead Boston, MA​/Stevens Point, WI

Salary Range

Boston: $75,000.00 To $ Annually
Stevens Point: $70,000.00 To $ Annually

Who are we? A strategic and trusted insurance partner, Berkshire Hathaway Specialty Insurance (BHSI), provides a broad range of commercial property, casualty and specialty insurance coverages and outstanding service to customers and brokers around the world. Part of Berkshire Hathaway’s insurance operations, we bring our solutions to market with our stellar brand name, top-rated balance sheet, and the expertise of our global team of professionals, who exude excellent capabilities and strong character.

We are a values‑based organization where respect, integrity, excellence, collaboration, and passion define who we are and how we do business. We value diversity of backgrounds, experience, and perspectives and strive to foster an inclusive environment that enables all our team members to bring their best selves to work. We are one team committed to building a culture where every teammate has the opportunity to contribute and be recognized.

Berkshire Hathaway Specialty Insurance (BHSI) is seeking a highly analytical and detail‑oriented Senior Technical Delivery Lead to join our Global Digital Services team based out of our Stevens Point, WI or Boston, MA office locations. This newly created role provides extensive exposure within a dynamic, rapidly expanding global insurance organization. We are looking for an individual with strong problem‑solving abilities and proven critical thinking skills to collaborate across departments and play a pivotal role in the design and development of systems and applications supporting our evolving insurance platform.

The ideal candidate will effectively integrate comprehensive data analysis into the company’s strategic objectives and help drive our Global Digital Services team’s operational performance.

• Oversee the full lifecycle of technical initiatives, ensuring timely, budget‑conscious, and high‑quality delivery aligned with insurance business goals.
• Translate complex insurance domain requirements into scalable Azure‑based technical solutions and delivery plans.
• Guide the design and implementation of cloud‑native solutions using Azure services such as App Services, Azure Functions, Logic Apps, and Azure Dev Ops.
• Champion Agile methodologies (Scrum, SAFe, Kanban), facilitating sprint planning, reviews, and retrospectives to drive iterative value delivery.
• Provide hands‑on technical direction and mentorship to engineering teams, fostering growth in cloud, integration, and modern development practices.
• Collaborate with enterprise architects to ensure solutions align with cloud‑first strategies, security standards, and regulatory compliance in insurance.
• Promote CI/CD pipelines, infrastructure as code (IaC), and automated testing using Git Hub and Git Hub Actions to accelerate delivery.
• Proactively identify, assess, and mitigate delivery risks, especially those related to data privacy, compliance (e.g., HIPAA, SOC
  2), and legacy system integration.
• Serve as the primary technical point of contact for business stakeholders, underwriters, actuaries, and claims teams to ensure alignment and transparency.
• Oversee integration with core platforms (e.g., ITSM, Observability, CI/CD) and ensure secure, scalable data flows APIs.
• Ensure delivery of high‑quality solutions through code reviews, automated testing, and performance monitoring, with a focus on reliability and maintainability.
• Ensure all solutions meet insurance industry regulations and internal security policies, including data encryption, access controls, and audit readiness.
• Drive retrospectives and feedback loops to improve delivery velocity, team collaboration, and technical excellence.
• Manage relationships with third‑party vendors, system integrators, and cloud service providers to ensure cohesive delivery and support.
• Promote modernization of legacy systems and adoption of emerging Azure technologies (e.g., AI, ML, OpenAI services) to enhance underwriting, claims, and customer experience.

• 7+ years of experience in technical delivery or…