Director, Vendor Strategy

Berkshire Hathaway Specialty Insurance•Boston, MA

22h•$160,000 - $185,000

About The Position

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.

Requirements

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.

Nice To Haves

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

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.