Vice President, Agile Enablement

Company: Berkshire Hathaway Specialty Insurance
Location: Boston
Posted on: February 16, 2026

Job Description:

Job Description Job Description 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. Want to be part of the team building the finest property, casualty, and specialty lines insurance company in the world? Learn more about our unique culture and history. Job Opportunity: Berkshire Hathaway Specialty Insurance (BHSI) has an exciting opportunity for an experienced senior technical leader to join us as Vice President, Agile Enablement as part of our Boston-based Technology team. This is a unique opportunity to join a global company and drive meaningful change to evolve how we work. This role sits within the Technology Strategy & Planning team and will regularly collaborate with executive and senior leaders across regions (e.g. North America, Europe, Asia Middle East, Australasia) and Global Functions. The VP will partner closely with technology and business stakeholders across Enterprise Architecture, Infrastructure & Digital Services, Cybersecurity, Application Development, and Operations. This leader will build a high-performing team and leverage partners to transform our technology delivery processes. The ideal candidate will have a passion for evolving technology delivery methodologies, strengthening partnerships across the global company, and cultivating a strong focus on measuring business outcomes. Success in this role requires excellent organizational and communication skills, a data?driven mindset, strong collaboration capabilities, and deep emotional intelligence. Duties & Responsibilities: Lead Agile transformation : Design and execute a comprehensive strategy to transform our globally distributed teams from a hybrid/waterfall SDLC to modern agile methodologies, including developing a plan to train/coach team members to evolve from current roles to agile roles (e.g. Business Analyst to Product Owner). Establish Agile governance : Develop standards, practices, and guardrails for Agile adoption across the organization. Implement measures of success to gauge agile maturity. Implement and optimize Agile tools : Drive adoption of agile backlog management and reporting tools (e.g. Azure DevOps, Jira). Define, Track, and Realize Value : Establish best practices and consistency around delivery metrics (predictability, quality, and business value delivery) and partner with key stakeholders to measure ROI and report on benefits realization. Coach through change management : Lead cultural and organizational change to embed Agile mindset and practices. Coach and mentor across all levels (executives, managers, and delivery teams) to embrace Agile mindset and servant leadership. Stakeholder engagement : Align Agile transformation goals with strategic priorities and communicate progress to senior leadership. Continuous improvement : Champion a culture of continuous improvement, ownership, and collaboration across business and technology teams to identify opportunities to enhance processes, tools, and team performance. Qualifications, Skills, and Experience: 15 years of progressive leadership experience in technology strategy, planning, or operations Proven record leading enterprise-wide Agile transformations and modernizing software development practice Deep understanding of portfolio management, governance, and workforce optimization in a global context Excellent communication and interpersonal skills with the ability to influence and collaborate across all levels of the organization Experience managing consultant relationships and implementing scalable sourcing strategies Exceptional change management, organization, and strategic thinking skills Expertise in Agile Frameworks: Deep knowledge of Scrum, Kanban, SAFe, and Lean principles Experience with Behavior Driven Development (BDD) and Gherkin syntax Proficiency in Jira or Azure DevOps: Hands-on experience configuring Agile boards, pipelines, and dashboards for enterprise reporting Strong analytical skills to interpret complex data and make informed decisions Ability to challenge the status quo and inspire followership Preferred Qualifications: Experience in insurance, financial services, or a similarly complex, regulated industry Portfolio/Agile Certifications such as PMP, PMI-ACP, CSP, ICAgile, SAFe, or similar Knowledge of Duck Creek Platform or equivalent P&C system and associated integrations BHSI Offers: A competitive package and exciting growth opportunities for career-oriented teammates. A dynamic, action oriented, and thoughtful environment centered on always doing the right thing for our customers, teammates, and our other stakeholders. A purposely non-bureaucratic organization that embraces simplicity over complexity and emphasizes individual excellence in a team framework. Benefits that support your life and well-being, which include: Comprehensive Health, Dental and Vision benefits Disability Insurance (both short-term and long-term) Life Insurance (for you and your family) Accidental Death & Dismemberment Insurance (for you and your family) Flexible Spending Accounts Health Reimbursement Account Employee Assistance Program Retirement Savings 401(k) Plan with Company Match Generous holiday and Paid Time Off Tuition Reimbursement Paid Parental Leave The base salary range for this position in Boston is $200,000 - $250,000 along with annual bonus eligibility. Total compensation for a candidate is determined by their relevant skills, location, and experience. We value our teammates – both their capabilities and character – as demonstrated by our amazing culture. NOTE: Compensation will be commensurate with experience. This job description is not intended to be all-inclusive. Team Member may perform other related duties as negotiated to meet the ongoing needs of the organization.

Keywords: Berkshire Hathaway Specialty Insurance, Pawtucket , Vice President, Agile Enablement, IT / Software / Systems , Boston, Rhode Island