Chief of Digital Services (Program Manager Senior IV)

MD; Baltimore (MD); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Flexible hours

Hybrid teleworking

Paid holidays

Generous leave

State pension

401(k) type plan

Health and dental plans

Flexible Spending Account

Job summary

Maryland Department of Labor seeks a Chief of Digital Services to lead the FAMLI division's digital portfolio. This role supervises Directors of Product, Engineering, and Experience Design, ensuring delivery quality and alignment with state requirements.

Responsibilities include setting an enterprise digital vision, guiding agile delivery, and coordinating cross‑functional teams to implement human-centered design across the program.

Qualifications

• Experience building an enterprise‑level digital services vision and strategy.
• Ability to lead multi-disciplinary teams to deliver iterative digital products.
• Strong decision-making, prioritization, and stakeholder alignment.
• Experience in agile frameworks (scrum/kanban) and vendor management.
• Commitment to human-centered design principles.

Responsibilities

• Provide strategic oversight and direction for FAMLI's overall digital strategy.
• Ensure timely delivery of FAMLI digital products within an agile environment.
• Lead the Digital Services team to build a cohesive culture and operationalize processes.
• Guide the transition from vendor-led to state-owned digital practices post-launch in 2028.
• Represent digital services across the division, department, and IT.

Skills

Digital leadership

Agile methodologies

Stakeholder alignment

Cross-functional leadership

User-centered design

Project management

Strategic vision

Effective communication

Vendor management

Job description

Introduction

Maryland’s Family and Medical Leave Insurance (FAMLI) program makes sure all workers in Maryland have paid time off for medical and family reasons. FAMLI is a social insurance system covering 2.6 million workers and 180,000 employers, delivered as a digitally native, public-facing service. We’re in the early stages of building something as big and as far-reaching as unemployment insurance or a new health department. We know that delivering services primarily through a website, over the Internet, is a new way of doing business in government.

Our Digital Services Team

Our Digital Services team brings a modern and cross-disciplinary approach to creating, launching, and continuously improving the digital services powering paid leave in Maryland. The team is responsible for providing human-centered experiences to workers who need to take paid leave, employers who need to provide paid leave, and FAMLI staff who process claims and provide direct support to the public. This is a rare chance to build a digital service from the ground up for the people of Maryland and a career-defining civic tech opportunity.

You should be

comfortable working in a startup environment where you think independently and operate with a high degree of autonomy. We’re looking for self-starters who are skilled at driving projects forward while communicating and collaborating closely on teams.

GRADE

26

LOCATION OF POSITION

Maryland Department of Labor
100 S. Charles Street
Baltimore, Maryland 21201

Main Purpose of Job

The chief of Digital Services leads the Digital Services Team, which is part of the Family and Medical Leave Insurance (FAMLI) Division of the Maryland Department of Labor (MD Labor). This role operates as the principal digital representative for the State FAMLI team, reporting to and carrying out priorities for the Assistant Secretary of FAMLI. This role serves as a subject matter expert (SME) on technology decisions as it relates to FAMLI's digital systems, and serves as an advisor to the Assistant Secretary. The Chief also acts to hold vendors accountable for deliverables. This role oversees the Directors of Product, Engineering, and Design to ensure quality and timeliness of digital deliverables, and that FAMLI and State requirements and priorities are integrated in the digital build for the program. This role directly supervises FAMLI's digital leadership-including the Director of Product, Director or Engineering, and Director of Experience Design and is responsible for holding directors accountable for managing their staff and ensuring delivery and quality of work is upheld in those areas. This role also serves as a chief point of contact in terms of project management responsibilities and reports and is held accountable for capabilities dependent on digital output.

Position Duties

Duties of this position include but are not limited to:
Provide strategic oversight and direction for FAMLI's overall digital strategy, making critical tradeoffs among competing priorities including security, privacy, delivery timelines, technical constraints, policy decisions, and high-quality service design for the public.
Ensure the timely delivery of FAMLI digital products by balancing technical constraints, oversight requirements, and design considerations within an agile development environment, supporting iterative delivery for a greenfield program with a strong focus on human-centered design.
Lead the Digital Services team to support the needs for the FAMLI program by building and maintaining a cohesive culture of alignment, trust, empowerment, and staff investment while directing the operationalization of Digital Services processes, structures, and initiatives.
Guide the Digital Services team through the transition from vendor-led product management to full state ownership of digital practice areas following full program launch in 2028.
Represent FAMLI's digital services directorates-engineering, design, and product across the FAMLI Division, the Maryland Department of Labor, and the Maryland Department of Information Technology.
Serve as the primary decision-maker for critical tradeoffs shaping FAMLI's digital strategy, ensuring alignment with program goals, operational needs, and effective public service delivery.

Minimum Qualifications

Experience: Experience working iteratively with users of digital products to build out, improve, and maintain those products. Experience developing an enterprise-level digital services vision and strategy and seeing through that vision to completion by leading multi-disciplinary teams. Strong decision-making and prioritization skills. Experience leading multi-disciplinary teams to translate an enterprise-level vision into a smooth and continuous delivery. Knowledge and experience with project management methodologies, principles, and processes. Experience building alignment with stakeholders. A strong understanding of the elements of leading a team on agile projects with agile rituals and ways of working (scrum, kanban, etc.). A history of having generated creative ideas to complex problems and followed through on the implementation of solutions. An ability to communicate effectively with technical and non-technical stakeholders, cross-functional teams, and across business lines. A demonstrated a commitment to human-centered design principles and an iterative approach to product development.

Desired or Preferred Qualifications

You value autonomy in your work, strive to achieve mastery in your field, and are energized by a mission-driven organization. You're a strong and inclusive leader who works well with people. You're an excellent collaborator who has a history of collaborating with non-technical peers and patiently and cheerfully explaining the ins and outs of product development to them. You know how to effectively manage teams who have potentially conflicting incentives. You are excited about both solving interesting technical issues and also complex human and organizational ones. You're an organized person who has experience coordinating complex projects. You're great at delegating ownership to capable people. You've got a tried-and-true approach to coordinating multiple development teams in the same ecosystem. You're on top of modern software development best practices and have contributed in environments where product managers, human-centered designers, user researchers, and software developers all collaborated. You've got strong core product management skills and know how to set an actionable enterprise level vision.

Special Requirements

All candidates are subject to a background check against files maintained by the Division of Unemployment Insurance (Labor/DUI) to determine whether any monies are owed to Labor/DUI as a result of unemployment insurance overpayment/fraud. Any unpaid debt may have an impact on whether or not a candidate is offered employment.

Selection Process

All information concerning the qualifications, including any required documentation (diploma, transcript, certificate, etc.) must be submitted and received by the closing date. Information submitted after this date will not be considered. Applications that meet minimum and/or selective qualifications will be referred to the hiring unit for interview selection. Units will select those candidates most closely demonstrating the qualifications for the interview.

Examination Process

The assessment may consist of a rating of your education, training, and experience related to the requirements of the position. It is important that you provide complete and accurate information on your application.

Benefits

This is a full-time, permanent position and eligible for full State Benefits, which include:

• Flexible hours and hybrid teleworking
• Paid holidays 12-13 per year
• Generous paid leave package (annual, sick, personal and compensatory leave)
• State Pension ('defined benefits' plan)
• Tax-deferred supplemental retirement savings plans (401(k) and 457)
• Comprehensive, subsidized health, dental prescription plans with little to no deductibles, free generic prescriptions, and free preventative health services
• Flexible Spending Account plan for Health Care and Daycare
• State Employees Credit Union