Director, Vendor Strategy

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:

BHSI is seeking an experienced and forward-thinking Director, Strategy & Planning, to lead Technology Vendor Strategy across our global technology organization. This role will build a disciplined, transparent, and outcome-focused approach to how BHSI selects, governs, measures, and evolves our technology vendor ecosystem. This is an individual contributor role with significant cross-functional influence.

This is a high-impact role for someone who brings vendor relationship management, strategic sourcing, workforce planning, financial insight, practical project leadership, and strong operating discipline. This person will help ensure BHSI engages the right partners for the right work, receives measurable value from each relationship, reduces unnecessary dependency risk, and uses external capabilities to accelerate business and technology outcomes without losing internal accountability or knowledge. As a key member of the Technology Strategy & Planning team, this person will manage related department initiatives, assist with department-wide activities, and keep important operational work moving with structure and follow-through.

The ideal candidate is a hands-on, analytical thinker who can move comfortably between vendor relationships, data analysis, project execution, and practical department operations. Success in this role requires excellent communication and relationship building skills, a data-driven mindset, and a high degree of self-awareness and emotional intelligence. This person should be equally comfortable building relationships, following up on details, preparing leadership-ready updates, and helping the Strategy & Planning team stay organized and effective.

Why this role matters: BHSI’s technology organization relies on external partners to extend capability, accelerate delivery, and support global operations. This role will help ensure those partnerships are intentional, well-governed, financially transparent, and connected to measurable business and technology outcomes.

Responsibilities:

• Lead and continuously evolve BHSI’s technology vendor strategy, governance framework, standards, and operating model so vendor decisions are consistent, transparent, and aligned to business and technology objectives.
• Develop vendor segmentation strategies that identify strategic partners, preferred vendors, niche providers, commodity services, and opportunities for consolidation or growth.
• Establish vendor risk and resiliency practices, including dependency management, business continuity considerations, and transition planning.
• Monitor vendor spending and resource utilization to ensure alignment with approved budgets, forecasts, and workforce plans.
• Partner with Technology and Finance leaders to develop annual vendor budgets, workforce forecasts, quarterly reforecasts, and monthly actuals reporting, providing analysis and recommendations to support investment decisions.
• Partner with Emerging Technology leaders to evaluate AI vendors, shape AI sourcing strategies, and support buy, build, partner, and retire decisions across the technology organization.
• Partner with Legal, Contract Management, Security, HR, and business stakeholders to optimize vendor engagement across sourcing, contracting, onboarding, renewals, and transitions.
• Advise Technology leadership on sourcing strategies, workforce models, and decisions regarding internal capabilities, staff augmentation, professional services, and strategic partnerships.
• Provide framework and support for vendor sourcing and selection activities, including market assessments, RFI/RFP processes, proposal evaluations, commercial reviews, and vendor recommendations.
• Develop and maintain strong vendor relationships, establish vendor scorecards and performance measures, facilitate business reviews, and provide recommendations to leadership on cost, quality, delivery, risk, contract compliance, and business outcomes.
• Drive vendor rationalization and consolidation efforts to improve transparency, reduce complexity, optimize spending, and strengthen strategic partnerships.
• Lead strategic initiatives related to vendor management, sourcing strategy, workforce transitions, operating model improvements, and other Technology Strategy & Planning priorities.

Qualifications, Skills and Experience:

• 10+ years of experience in technology vendor management, strategic sourcing, procurement, technology finance, consulting, or a related field, with demonstrated exposure to technology services, vendor governance, commercial analysis, and cross-functional stakeholder management.
• Proven experience developing and executing vendor strategies, governance models, sourcing approaches, and vendor management practices.
• Strong understanding of technology services and commercial models, including staff augmentation, professional services, managed services, and software licensing.
• Experience leading vendor selection activities, including market assessments, RFI/RFP processes, contract negotiations, commercial evaluations, and vendor recommendations.
• Strong financial and analytical skills, including budgeting, forecasting, monthly actuals management, spend analysis, workforce planning, and investment decision support.
• Demonstrated success leading complex cross-functional initiatives involving multiple stakeholders, competing priorities, and organizational change.
• Strong communication, relationship management, negotiation, and influencing skills, with the ability to build partnerships and provide recommendations to senior leaders.
• Ability to operate effectively in a fast-paced environment, bring structure to ambiguity, and balance strategic thinking with hands-on execution.
• Strong project management and operating discipline, with the ability to manage details, follow through on commitments, and keep cross-functional work moving without adding unnecessary bureaucracy.
• Curiosity and learning agility, with the ability to stay current as technology services, AI vendor models, outsourcing trends, commercial practices, and third-party risks evolve.
• Proven ability to lead with self-awareness and emotional intelligence, adapting style based on context and feedback while maintaining accountability.

Preferred Qualifications:

• Experience in insurance, financial services, or other regulated, data-sensitive industry preferred
• Experience with global/offshore technology delivery models (agile, lean) and distributed vendor teams preferred
• Experience with Evisort or similar contract lifecycle tools helpful

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 $160,000 to $185,000, along with annual bonus eligibility; a candidate’s salary is determined by their relevant skills 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.