Deputy Director of Digital Workplace and Collaboration at Massachusetts Bay Transportation Authority – Boston, Massachusetts

The Deputy Director of Digital Workplace and Collaboration will lead and evolve MBTA’s digital productivity environment. This pivotal role will oversee two key teams: one focused on the support and adoption of the entire Microsoft 365 (M365) suite and other core productivity applications, and a second team dedicated to managing and enhancing specialized Digital Workplace applications, such as Comply365, Asana, Miro, DocuSign, etc.

Leadership & Strategy

• Strategic Vision:Develop and execute a comprehensive strategy for the Digital Workplace, ensuring alignment with overall business objectives and technology roadmap.
• Team Management:Provide clear direction, mentorship, and performance management to two distinct teams: the M365/Productivity Applications Team and the Digital Workplace Applications Team.
• Roadmap & Portfolio:Own the roadmap for the entire portfolio of digital workplace and collaboration tools, prioritizing projects and initiatives that deliver the highest ROI and user benefit.
• Budget Management:Assist in planning, forecasting, and managing the operational and capital budgets for managed applications and teams.

Microsoft 365 & Core Productivity

• Oversight:Direct the team responsible for the planning, implementation, support, and governance of all M365 applications (e.g., Teams, SharePoint, CoPilot, OneDrive, Power Platform) and other core productivity tools.
• Adoption & Change Management:Drive successful user adoption through effective communication, training strategies, and change management initiatives across the M365 suite.
• Security & Compliance:Ensure M365 and core productivity application environments adhere to the organization's security policies, compliance standards, and data governance frameworks.

Digital Workplace Applications

• Application Management:Oversee the team managing the lifecycle of specialized digital workplace applications, ensuring high availability, performance, and integration with other enterprise systems.
• Process Optimization:Collaborate with business units (e.g., Compliance, Operations) to identify opportunities for leveraging these applications to streamline complex workflows and reporting.
• Vendor Management:Manage relationships, contracts, and service level agreements (SLAs) with key application vendors.

Operational Excellence

• Service Delivery:Ensure high-quality and timely support (Tier 2/3) for all managed applications, establishing and monitoring key performance indicators (KPIs) and SLAs.
• Innovation:Actively research and recommend emerging technologies and features within the digital workplace space to maintain a competitive and efficient operating environment.

Team Development

• Recruit, develop, and retain a high-performing applications team, providing mentorship and career growth opportunities.

• Foster a supportive and collaborative team environment, encouraging professional development and knowledge sharing.

Supervision

• Direct supervision of one or more Managers, Analysts, and Engineers.

• Bachelor’s degree from an accredited institution in Computer Science, Information Technology, Business Administration, or a related field.
• Seven (7) years of progressive experience in Information Technology application support and infrastructure.
• Five (5) years of leadership, managerial, and/or supervisory experience.
• Deep, demonstrated expertise in the Microsoft 365 ecosystem (Teams, SharePoint, OneDrive, Governance, Security, and Compliance features).
• Proven experience managing and supporting specialized commercial or custom off-the-shelf (COTS) applications, with familiarity in highly regulated environments (e.g., knowledge of applications like Comply365 or similar GRC/document management tools).
• Strong ability to lead, motivate, and develop diverse technical teams.
• Exceptional verbal and written communication skills, capable of translating complex technical concepts for executive leadership and end-users.

• A high school diploma or GED with an additional seven (7) years of directly related experience substitutes for the bachelor’s degree requirement.
• An associate’s degree from an accredited institution and an additional three (3) years of directly related experience substitutes for the bachelor’s degree requirement.
• A master’s degree in a related subject substitutes for two (2) years of general experience.
• A nationally recognized certification, or statewide/professional certification in a related field substitutes for one (1) year of experience.

Preferred Experience and Skills

• Direct experience in establishing and enforcing governance policies for key M365 services, particularly SharePoint Online, Teams, and the Power Platform (Power Apps, Power Automate). This includes provisioning, external sharing controls, and lifecycle management.
• Experience with the principles of Enterprise Content Management (ECM) and its application within M365 or with specialized ECM/Compliance platforms like Comply365.
• Knowledge of how to integrate collaboration tools with major enterprise systems like ERP, CRM, and HR platforms, often utilizing API management and middleware.
• Experience defining, tracking, and reporting on key Digital Workplace KPIs, such as user engagement rates, service utilization, adoption progress, and platform ROI.
• Experience or interest in the public transit or transportation industry.