Vice President, Agile Enablement

Berkshire Hathaway Specialty Insurance•Boston, MA

6d•$200,000 - $250,000•Onsite

About The Position

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.

Requirements

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

Nice To Haves

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

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.