About The Position

Travelers is seeking a Senior Director, Delivery Lead to join our organization as we transform and modernize our technology portfolio. In this position, you will leverage your expertise to develop and evolve a multiyear technology transformation roadmap focused on delivering modern capabilities that enable business strategies . Lead and influence strategic decisions about capability sequencing based on business value, technical dependencies, and organizational readiness. Partnering with multiple stakeholders across lines of business to deliver a portfolio of solutions and capabilities with responsiveness/speed to market, efficiency, predictability, and quality. This role may manage others.

Requirements

  • 4 years of relevant technology experience.
  • 3 years of people management or team leadership experience.
  • 3 years of Program Management in an Agile environment or related experience required
  • Bachelor’s degree.
  • 7+ years of progressive experience in technology strategy, transformation leadership, or related strategic roles.
  • Experience leading technology transformations in financial services, insurance, or other heavily regulated industries where change must be carefully managed.
  • Proven track record driving results through influence in complex organizations - you've successfully shaped senior leader decisions by translating technical complexity into business value narratives.
  • Strategic thinking abilities with track record of translating vision into executable, value-driven roadmaps for technology investments at enterprise or division scale.
  • Understanding of enterprise architecture and how to introduce new capabilities into complex technology ecosystems.
  • Experience determining when to sunset legacy capabilities based on adoption metrics and business value.
  • Strong technical knowledge and a deep strategic mindset.
  • Proven analytical skills and experience making decisions based on hard and soft data.

Nice To Haves

  • Programming/development experience is preferred.

Responsibilities

  • Optimize the flow of valuable solutions in a multi-team environment by reducing dependencies, hand-offs, and systemic waste.
  • Plan and facilitate Program Increment planning events; ensure work is incorporated in Program Increment plans and capacity is reserved for technical and operational enablers, refactoring, and unknowns.
  • Build feedback loops through cross-team reviews and engage all key stakeholders, promoting faster learning cycles.
  • Drive relentless improvement through multi-team retrospectives, metrics, assessment analysis, and other means.
  • Escalate and track risks and impediments to eliminate systemic waste to improve the flow of value.
  • Create transparency into the progress of cross-team work through visible boards, operational metrics, forums, dashboards, etc.
  • Manage cross-team dynamics.
  • Coordinate team building and cross-team communication.
  • Promote and teach effective software delivery practices.
  • Provide input on resourcing to address critical bottlenecks.
  • Perform other duties as assigned.

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.

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What This Job Offers

Job Type

Full-time

Career Level

Director

Number of Employees

5,001-10,000 employees

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