Director of Enterprise Applications - HCM

Millions of people interact with the City of Boston digitally each year to do everything from finding information on City services to paying a parking ticket. We believe these experiences should be easy to navigate and accessible. The Department of Innovation and Technology (DoIT) is focused on partnering with City departments to improve service delivery across the City. We’re a cross‑functional team with a mission to improve the user experience of existing digital services, better engage and communicate with our residents, and build new systems to improve how the City delivers services online.

DoIT provides and maintains mission‑critical technologies for the City’s more than 18,000 employees and the hundreds of thousands of constituents they serve.

DoIT is looking for a Director of Enterprise Applications to lead the technology team that builds and sustains our Human Capital Management (HCM) enterprise platform (currently, PeopleSoft HCM). The Director of Enterprise Applications will serve as the executive owner of the City's Human Capital Management enterprise platform, providing both strategic direction and hands‑on leadership to ensure the successful planning, delivery, operation, and continuous improvement of enterprise HCM solutions that support the City's workforce and business objectives. They’ll develop internal partnerships and work across business functions to keep technology execution aligned with business goals. They’ll inspire and lead their team through change in the continual pursuit of working better and smarter for the people of Boston.

Team Leadership and Practice Building:

• Direct and oversee the strategic and operational activities of the City's HCM enterprise platform team, a diverse team of business analysts, platform developers, and project delivery staff.
• Establish long‑range workforce, succession, and resource strategies to support the continued evolution of the City's enterprise HCM technology system.
• Provide executive oversight of technology contracts, vendor partnerships, service agreements, and operating budgets, ensuring fiscal stewardship, contract compliance, and business outcome achievement.
• Set clear goals, provide regular feedback, and create professional development opportunities for team members.
• Foster an inclusive team culture that encourages innovation, experimentation, and growth.
• Build the product management community of practice along with product leaders across the Cabinet to establish shared tools, processes, and knowledge.

Strategy:

• Lead the strategic vision and governance for enterprise HCM platforms, partnering with executive leadership to align technology roadmaps with overarching City priorities.
• Communicate experience improvement intentions through strategic roadmaps that convey how value will be delivered.
• Seek out opportunities to improve our operations and drive them to successful outcomes.
• Drive technology strategy decisions as the commercial solutions landscape evolves.
• Engage with peer organizations to share practices, advocate to vendors, and represent the City’s interests in our technology ecosystem.

Stakeholder Management:

• Establish and maintain executive‑level partnerships with City leaders and external stakeholders to keep enterprise technology decisions aligned with operational goals and objectives over the long term.

Delivery:

• Direct the successful execution of the enterprise HCM portfolio by establishing operational priorities and trade‑offs, governance practices, performance standards, and resource allocation strategies.
• Leverage agile principles and modern design and development practices, and ensure all work delivers value quickly and continually.
• Ensure compliance with technology and security standards and support periodic audits.
• Identify and escallate risks, delays, or system vulnerabilities; manage high‑priority production support incidents.

User Experience:

• Ensure that our technology decisions are informed by end users and that user research, data and user feedback are considered as the roadmap and product priority choices are made.
• Ensure a consistent, dignified, and ideally delightful end‑to‑end user experience across products and channels.

Product Operations:

• Drive team adoption and optimization of the software development lifecycle process.
• Lead large‑scale system updates.
• Develop and maintain an operating model for production support.
• Perform related work as required.

• At least five (5) years of full‑time, or equivalent part‑time, professional experience with progressive leadership in a software product management or digital service delivery role, or a related field.
• A Bachelor’s degree is required. A Master’s degree in Information Systems, Computer Science, Business Administration, Public Administration, Information Technology, or a related field may be substituted for up to three (3) years of the required experience.
• Excellent analytical and problem‑solving skills.
• Strategic thinking: ability to define and articulate a multi‑year product vision and strategy, along with an ability to build buy‑in across the team, our government partners, and other collaborators.
• Leadership experience among cross‑functional teams that work collaboratively to build new capabilities.
• Experience being accountable for business decisions where ambiguity exists and trade‑off choices must be made.
• Experience delivering enterprise software capabilities within large organizations and ensuring the successful adoption of those capabilities into ongoing operations.
• Organizational skills sufficient to manage a dynamic portfolio of work that spans teams, customers, cultures, and technologies.
• Written and verbal communication skills that generate trust and convey complex technical ideas effectively among diverse audiences, particularly at executive levels.
• A proficiency with standard office productivity applications (e.g., Google Workspace, Microsoft Office), software lifecycle management platforms (e.g., Jira) and visual communication and ideation tools (e.g., Miro, Visio) is required.
• Ability to exercise good judgment and focus on detail as required by the job.

Preferred:

• Deep functional or technical knowledge of PeopleSoft HCM (Core HR, Payroll, Time and Labor, Absence, Benefits, ePerformance).
• Proven ability to manage and lead an enterprise technology platform team through organizational change.
• General knowledge of current Payroll, Benefit, and Human Resource management practices, especially in the public sector.
• Knowledge of public sector regulatory requirements that apply to employer/employee relationships.
• History of successful delivery of projects following an Agile methodology.
• Deep knowledge of industry and market trends and the landscape of commercially available solutions that will affect product direction.
• Understanding of user‑centered design methods and usability best practices.
• Familiarity with database queries and system integration design considerations.

BOSTON RESIDENCY REQUIRED

Terms:

Union/Salary Plan/Grade: Non‑Union/MM2-11

Hours per week: 35