Director, Strategic Initiative – Claim Technology

Role Overview

• The Director, Strategic Initiatives leads planning & execution functions with accountability to drive effective execution of departmental projects and initiatives enabling successful achievement of Claims' multi-year technology transformation roadmap.
• You will be responsible to plan for the full lifecycle of the investment
• partnering to define scope, benefit and estimating costs, through evaluating sourcing approaches, understanding new technology needs as well as implications with existing technology assets, preparing for and supporting execution to ensure successful implementation and value realization.
• Leading through influence in a matrixed agile environment, you will partner with cross-functional teams and stakeholders throughout the investment lifecycle, making informed trade-offs that optimize business value, technology modernization needs while managing risk.
• Build and maintain strong relationship within business leadership team.
• Partner with other organizations, inclusive of other Strategic Planning & Execution organizations (SP&E), to ensure alignment on purpose, progress, and resource requirements needed to achieve business objectives.
• Partners closely with Business Unit leadership to drive the alignment to strategy/planning for execution of strategic priorities including multi-year planning, resource planning, initiative prioritization and strategic roadmap development.
• Drive effective management and execution of ongoing investment portfolio, close gaps between strategy development and execution and ensure strategy and budget alignment across.
• Design and implement strategic planning infrastructure and ensuring clear processes, documentation and operating model to drive effective direction and ensure alignment of organization to overall goals and vision.
• Establish and implement departmental reporting framework including reporting packages and regular analysis & report out of results, ensuring stakeholders are informed and support leadership in making key decisions.
• Provides strong strategic leadership, direction, and execution focus to Strategy, Planning and Portfolio team, leading with a diverse and inclusive mindset and proactively engaging team members so they reach their full potential.

Requirements

• Bachelor’s degree in a related field
• 5+ years of progressive experience leading complex technology investments in large, regulated organizations (financial services, healthcare, insurance, or similar industries where change requires careful stakeholder management)
• Proven track record owning and managing investment plans through the full lifecycle
• from business case development and cost estimation through sourcing strategy, implementation, and value realization
• 5+ years leading delivery in scaled agile environments (SAFe, LeSS, or similar frameworks)
• Demonstrated success preparing teams for execution through effective planning and dependency management
• Strong capability in identifying, tracking, and mitigating risks throughout the investment lifecycle, escalating appropriately and adjusting plans to maintain progress toward outcomes
• Demonstrated ability to estimate total cost of ownership and track financial performance against estimates throughout the investment lifecycle, managing scope and budget adjustments as needed
• Experience evaluating build vs. buy decisions, sourcing approaches, and vendor partnerships to optimize investment outcomes
• Experience identifying technical dependencies, integration requirements, and migration strategies when introducing modern capabilities alongside legacy systems
• Ability to engage credibly with technical teams on architecture decisions, technical trade-offs, and implementation approaches without requiring hands-on engineering experience
• Demonstrated success preparing teams for execution through effective planning and dependency management
• Analytical mindset with experience making data-driven decisions throughout the investment lifecycle
• Ability to translate technical complexity into business value narratives that resonate with non-technical stakeholders
• 5 years of project management experience.
• Experience working with project-management methodologies and Agile principles.
• Experience in developing strong, trusted partnerships with senior executives and constituent partners.
• Ability to lead and inspire team members to achieve optimal results in a highly collaborative and matrixed organization.
• Systemic thinker with strategic planning expertise, readily sees patterns and connections in a complicated environment.
• Demonstrated ability to put strategic plans into action.
• Strong facilitation and conflict resolution skillset.
• Experience managing multiple complex projects simultaneously.
• Strong analytical and problem-solving skills.
• Understanding and appreciation for business, business intelligence/analytics, and technology components of program/portfolio management.

Benefits

• Health Insurance : Employees and their eligible family members – including spouses, domestic partners, and children – are eligible for coverage from the first day of employment.
• Retirement: Travelers matches your 401(k) contributions dollar-for-dollar up to your first 5% of eligible pay, subject to an annual maximum. If you have student loan debt, you can enroll in the Paying it Forward Savings Program. When you make a payment toward your student loan, Travelers will make an annual contribution into your 401(k) account. You are also eligible for a Pension Plan that is 100% funded by Travelers.
• Paid Time Off: Start your career at Travelers with a minimum of 20 days Paid Time Off annually, plus nine paid company Holidays.
• Wellness Program: The Travelers wellness program is comprised of tools, discounts and resources that empower you to achieve your wellness goals and caregiving needs. In addition, our mental health program provides access to free professional counseling services, health coaching and other resources to support your daily life needs.
• Volunteer Encouragement: We have a deep commitment to the communities we serve and encourage our employees to get involved. Travelers has a Matching Gift and Volunteer Rewards program that enables you to give back to the charity of your choice.