Vice President, Agile Enablement

Overview

Berkshire Hathaway Specialty Insurance (BHSI) is a strategic and trusted insurance partner providing a broad range of commercial property, casualty and specialty insurance coverages and outstanding service to customers and brokers around the world. We are part of Berkshire Hathaway’s insurance operations, and we bring our solutions to market with our strong brand, top-rated balance sheet, and the expertise of a global team of professionals who exude capability and strong character.

We value diversity and strive to foster an inclusive environment where every teammate can contribute and be recognized.

BHSI has an exciting opportunity for an experienced senior technical leader to join us as Vice President, Agile Enablement, on the Boston-based Technology team. This role sits within the Technology Strategy & Planning team and collaborates with executive and senior leaders across regions and Global Functions. The VP will partner with technology and business stakeholders across Enterprise Architecture, Infrastructure & Digital Services, Cybersecurity, Application Development, and Operations.

The leader will build a high-performing team and leverage partners to transform technology delivery processes.

• Lead Agile transformation:
  Design and execute a comprehensive strategy to transform globally distributed teams from a hybrid/waterfall SDLC to modern agile methodologies, including training/coaching 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 Dev Ops, Jira).
• Define, Track, and Realize Value:
  Establish best practices and consistency around delivery metrics (predictability, quality, and business value delivery) and measure ROI with stakeholders.
• Coach through change management:
  Lead cultural and organizational change to embed Agile mindset and practices. Mentor across all levels 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 to enhance processes, tools, and team performance.

• 15+ years of progressive leadership experience in technology strategy, planning, or operations.
• Proven record leading enterprise-wide Agile transformations and modernizing software development practices.
• 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:
  Scrum, Kanban, SAFe, and Lean principles.
• Experience with Behavior Driven Development (BDD) and Gherkin syntax.
• Proficiency in Jira or Azure Dev Ops:
  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.

• 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 integrations.

• A competitive package and exciting growth opportunities for career-oriented teammates.
• A dynamic, action-oriented, and thoughtful environment centered on doing the right thing for customers, teammates, and stakeholders.
• A non-bureaucratic organization that embraces simplicity over complexity and emphasizes individual…