Director of Digital Transformation

Boston, MA
Customer Technology – Director /
At the Technology Innovation Department (TID), our mission is to apply modern principles of research, design, and technology to make our transit system easy for all riders to use. Effective and equitable public transit is essential to the social, economic, and environmental progress of Greater Boston.
The MBTA Technology Innovation team is working to transform how people get around the Boston area.
We are a team of designers, engineers, product and content specialists charged with bringing novel ideas, modern standards and a user-centered approach to technology at the T. As the MBTA works to reinvent itself, we have a rare opportunity to craft the future of transportation for Boston and communities all around Eastern Massachusetts, as well as pioneer innovations for other transit agencies around the country.
Do you want to improve the daily transportation experience for 4.7 million people in the Boston region? Ready for the challenge? Then read on.

The Technology Innovation Department (TID) is seeking aDirector of Digital Transformation to be a program area lead role on internal-facing (i.e., non-rider-facing) digital work.This director will re-establish the program area into a cohesive team that is a leading example for other transit agencies. The program area’s mission is to apply the modern principles of research, design, and technology to help the MBTA and all of its staff work more efficiently, equitably, and safely. 
TID program area leads sit at the intersection of end users, MBTA stakeholders, and TID’s product development teams. They are responsible for the vision, strategy, partnerships, and execution of TID’s work in their program area. 
The digital transformation program area is currently a collection of modernization projects including instructional design, critical event management and communications, process improvement & digitization, MBTA-wide information & technology strategy, and more. 
While that is the current portfolio, the program area needs strong leadership to shape, structure, and focus what the portfolio of work ought to be and how it ought to be approached by using Service Design methodologies. Other opportunities could include data systems and integrations (e.g., data lake); operations, capital, and/or engineering & maintenance process design; and/or major in-house software builds to address a “job to be done”. 
While the Director of Digital Transformation is being hired to lead the digital transformation program area today, both the scope of the digital transformation program area and the assignment of this director to this program area may change as the needs of TID or the MBTA change.  
As a leader in TID and the MBTA, the Director of DigitalTransformation has an obligation to serve departmental and MBTA-wide goals and objectives. 

Duties and responsibilities:

    • Specifically, the Director of Digital Transformation’s duties and responsibilities are: 

    • To articulate, and advocate for, a vision for the future state of Digital Transformation, and how this furthers the objectives of the MBTA by making the organization more efficient, equitable, and safe. 

    • Develop, articulate, and get institutional buy-in for the vision for the program area 
    • Advocate for that vision—and the “voice of the staff,” generally—with internal and external stakeholders, including partner departments, vendors, & MBTA leadership 
    • Assemble and work as a self-contained “tiger team” across functional (Engineering, Design, Research, Product)disciplines 
    • Establish product and project teams around that vision 

    • To maintain a strategy and plan for the execution of work. 

    • With functional and cross-departmental peers, scope the product (i.e., software) and project (i.e., non-software) work that needs to happen to achieve the vision, and maintain a high-level prioritization 
    • In collaboration with functional (Engineering, Design, Research, Product) leads, create a staffing plan (how many of what types & levels of expertise of staff) that changes as needed over time that ensures the team is set up to successfully execute 
    • In collaboration with finance and administration, create and execute on a long-term budget: ensuring there is the right amount and type(s) (capital and operating) of funding over time. This includes drafting periodic budgets, capital requests, etc. as required. 

    • To manage and lead the execution of work. 

    • Lead the product and project teams responsible for execution in the program area  
    • Set standards for the quality of delivery 
    • Continually identify, escalate, and mitigate risks to successful execution 
    • Execute on projects, procurements, and vendor management as necessary 

    • Manage people toward the outcome of “putting them in a position to be successful,” centered on upholding the working agreements 
    • Directly manage program and project managers, responsible for all non-software development work 
    • Indirectly supervise the work of product teams, partnering with functional peers as needed 

    • Proactively build and maintain relationships with internal stakeholders (i.e., other MBTA departments) and external stakeholders (e.g., vendors, partners, transit agency peers) who are critical to the success of the program area in achieving its vision 

    • Maintain an understanding of approval-chains and executive notification procedures, as any piece of work might require 

    • Proactively identify new ideas, cross-departmental partnerships, and funding opportunities that might further the objectives of the program area 
    • Lead early-stage discovery, scoping, or refinement of new projects, pilots, or partnerships 

    • To serve departmental and MBTA-wide goals in addition to goals of Digital Transformation 

    • Practice and uphold TID’s working agreements, which are essential to the department’s success. 
    • Represent TID's work across the MBTA, and MBTA's work within the industry 
    • Contribute to and advance the overall MBTA technology strategy  
    • Coordinate team responses to competing requests, priorities, and strategic initiatives  
    • Work with the Chief Digital Officer on key digital initiatives  
    • May represent the MBTA and the Technology Innovation Department at external meetings with appropriate authorization (e.g., advocacy groups, rider feedback, media inquiries, industry groups)  
    • Design and implement relevant policies and programs to ensure that the Authority meets or exceeds all federal, state and local laws and regulations governing accessible public transportation, principally the Americans with Disabilities Act (ADA) of 1990, while ensuring that operations are provided in the most cost-effective and appropriate manner possible   
    • Respond to each inquiry, whether from a customers, vendor, or co-workers, in a professional and courteous manner   
    • Collaborate with other departments to improve access efforts within the MBTA  
    • Perform related duties and projects as assigned  


    • Direct supervision of up to 15 employees or contractors such as Deputy Directors, Program Managers, Project Managers, and System Administrators. Responsibilities may include (where appropriate) hire/terminate, performance management, and mentoring.  
    • Indirect supervision of up to 30 employees or contractors who work on products or projects in the program area. These staff report to discipline-specific managers within Customer Technology (e.g., Software Engineering, Design), but the Director of Rider Tools works with these “functional” managers to ensure these staff receive proper guidance.  

Work experience guidelines:

    • Although we're mostly interested in your ability to do the work, here are some guidelines on the capabilities and experience we think might be most suited for this role. Please keep in mind that the experience guidelines are advisory, and not required. 

    • Effective organizational, time management, interpersonal and multi-tasking skills    
    • Excellent customer service skills, with a proven ability to build trusted relationships with clients, internal business customers, or external customers (e.g., riders).   
    • Excellent communication and presentation skills with ability to influence people at all levels of the organization, both vertically and horizontally, as well as outside the organization  
    • A realistic sense of urgency grounded in data and long-term sustainable practices Experience using modern collaboration technologies for task management (we use Asana), document collaboration (we use Office 365), whiteboarding (we use Miro), and team chat (we use Slack primarily and also Microsoft Teams in limited circumstances).   

This role is hybrid. While most activities can be accomplished remotely, an important component of this role requires an in-person element.

As a contracted role for the MBTA, we are unable to hire candidates who would perform their work in California, Connecticut, Washington DC, Hawaii, New Mexico, Pennsylvania, South Dakota, Washington, West Virginia, and Puerto Rico.

At this time, we are only able to hire US residents who will reside in the US for the duration of their employment


Pay rate range is $106 - $124 per hour (W-2), up to 1880 hours per year.

Diversity, Equity, and Inclusion:

TID is dedicated to creating a diverse and inclusive environment—it’s essential to the work we do. In order to effectively partner with MBTA departments and do our best work for riders, our team must reflect the wide variety of people who use the MBTA’s services. We welcome people with different strengths, experiences, and backgrounds who share a passion for improving people's lives. Our team is deeply committed to diversity, inclusion, and continual learning. We strive to foster an environment where each individual is valued, feels a sense of belonging, and is welcomed to bring their best self to work.

Here at TID, we provide equal opportunity for all employees and applicants. We recruit, hire, train, promote, compensate, and manage all personnel without regard to race, color, national origin, cultural identification or expression, socioeconomic background, religion, gender, gender identity or expression, sexual orientation, family status, marital status, learning style, neurodiversity, genetics, disability, age, veteran status, or any other non-merit based or legally protected grounds. 

Research has shown that women and people of color are less likely to apply for roles unless they believe they meet all qualifications. We strongly encourage candidates from marginalized groups to apply, even if you don't believe you meet every one of the job qualifications listed. We’re committed to maximizing the diversity of our team and want to hear from anyone who is passionate about our efforts and interested in supporting our work for riders.