Director of Digital Transformation

Published July 9th, 2024

(Mostly remote- will have to go on site to New Haven occasionally).


The Director of Digital Transformation Office provides oversight of the companies Digital Transformation Office (DTO), establishing the structure to set up and manage multiple strategic initiatives at scale with consistent execution approaches, driving change management efforts and ensuring value delivery.
The DTO Director must have the ability to understand the business capabilities, develop and cultivate stakeholder relationships, and guide successful outcomes across multiple business units and complex programs to meet the organization’s strategic goals and objectives. The DTO Director drives impact and minimizes value leakage by focusing on delivering value through initiatives vs. simply tracking progress. The DTO Director drives the day-to-day processes with relentless focus on fact base to support value delivery and change management.
The DTO will establish and manage a digital transformation roadmap aligned with business priorities, evaluate program health of key initiatives, and intervene in programs to ensure they reduce risks, drive actions, and deliver successfully. The DTO will support dealing with cross-program dependencies, resource constraints, vendor performance, finances and invoicing, reporting, and transitions from transformational states to steady state operations.
The DTO’s objective is to help select programs to be staffed appropriately, negotiate allocations, and minimize distractions on those resources with regards to daily operations and lower priority work efforts. This includes being able to manage in a matrixed environment and collaborating effectively with steady state delivery and support teams.

Core Responsibilities


  • Supports strategic planning with business and IT.
  • Collaborates with Enterprise Strategic Portfolio Management capability and leadership
  • Conducts research to solve complex business and technology challenges.
  • Supports development and presentation of business cases for strategic initiatives.
  • Support the prioritization of requests, scoping efforts, budgeting, staffing, and funding for new digital transformation initiatives.
  • Supports digital transformation roadmap creation and sequencing, and clear communication to realize transformation impacts.


  • Establishes and manages transformation methodology and approaches.
  • Ensures programs are appropriately planned and adhere to the methodology.
  • Monitors, measures and assesses health of key programs identifying immediate actions to improve outcomes.
  • Collaborates with Business and IT leaders as part of a matrixed organization to achieve the goals of stakeholders.

Skills Qualifications


  • Demonstrated experience in problem solving, stakeholder management, business and digital acumen, analytical thinking and communication.
  • Proven track record of leading, managing and developing high performing teams
  • Possesses a full range of application management, strategic management, business process improvement, financial management, strong leadership and influencing skills
  • Expertise with a broad base of digital web and mobile products, technologies, platforms, patterns, frameworks, and methodologies
  • Excellent presentation and communication skills
  • Understands, explains and presents complex ideas to audiences at all levels in a persuasive and convincing manner
  • Has a broad and deep business knowledge, including the activities and practices of other organizations
  • Has a deep understanding of the industry and the implications of emerging technologies for the wider business environment
  • Experienced in application management delivery methodologies (agile, iterative, DevOps, waterfall, testing, micro-services, lean six sigma, etc.)
  • Knowledgeable in IT Service Management and experienced in ITIL Service Design, Service Operation and Service Transition
  • Ability to successfully resolve conflicts
  • Ability to drive and move a team to completion of goals
  • Prove track record of developing staff
  • Experience in a multicultural environment



  • BS or BA in Computer Science or Business Administration
  • 10-15 years of IT and business experience with at least 5 years of leadership experience in managing multiple, large, cross-functional teams or projects and influencing senior level management and key stakeholders or equivalent combination of training and experience
  • PMI / Prince 2 certification desired
  • ITIL Foundation certification desired
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