Senior Engineering Program Manager - Remote United States + Apply + + + + About CentralSquare Technologies CentralSquare is a unique enterprise software company whose mission is to build safer, smarter, more connected communities. More than 8,000 public sector agencies trust CentralSquare solutions each and every day. We serve governments of all sizes, from small towns to major cities, to make delivering public services less costly and more efficient. Job Description At CentralSquare, you’ll get the opportunity to work in a collaborative environment within a company that builds complex web-based enterprise applications for our Public Servants across North America. As over 250 Million citizens in the US are impacted by CentralSquare Software, we are on a trajectory to revolutionize the way agencies address citizens’ needs by improving quality of life and building safer, smarter communities...and we need great candidates to do it! Looking to grow your career? That’s great! Hard work should be rewarded, and we are committed to cultivating careers while providing competitive compensation and a great benefits package, including tuition reimbursement, parental leave, paid volunteer hours, and unlimited PTO. Our flexible work environment also enables you to take advantage of an excellent work-life balance whether you are in office or working remotely. The Role We are looking for a seasoned and highly capable Senior Program Manager to lead one of our Agile Release Trains (ARTs) and support the continued rollout of the Scaled Agile Framework (SAFe) across our product development organization. This role combines delivery leadership with agile coaching — ideal for someone who thrives at the intersection of program execution, systems thinking, and organizational change. You’ll be responsible for facilitating ART events, removing impediments, and aligning multiple cross- functional teams toward shared objectives. At the same time, you’ll help mentor and coach teams and leaders as we deepen our SAFe maturity. This is a strategic and influential role that requires both operational precision and a passion for continuous improvement. Key Responsibilities: + Agile Release Train (ART) Leadership + Serve as the Release Train Engineer (RTE) for one or more Agile Release Trains, coordinating all program-level activities and dependencies. + Facilitate key ART ceremonies, including PI Planning, Scrum of Scrums, System Demos, and Inspect & Adapt (I&A) events. + Track progress toward PI objectives, manage risks and dependencies, and drive transparency through reporting and metrics. SAFe Practice Development & Coaching + Partner with agile coaches, engineering managers, and product leaders to guide the organization through the SAFe transformation journey. + Help train teams and leaders on SAFe roles, principles, and practices; support the development of Lean-Agile mindsets. + Recommend improvements and coach teams on adopting SAFe practices in a way that aligns with the company’s culture and goals. Program Execution & Coordination + Coordinate across multiple agile teams, stakeholders, and technical dependencies to ensure timely delivery of high-quality features and services. + Monitor and resolve cross-team blockers, escalate issues where appropriate, and ensure alignment across teams and domains. + Collaborate with product management and architecture to ensure the ART is well aligned to business strategy and technical direction. Metrics, Reporting, and Visibility + Define and report on key performance indicators (KPIs) that reflect ART health, predictability, and flow. + Provide clear, actionable insights to senior leadership on program status, risks, and improvement opportunities. + Support the adoption and effective use of tooling (e.g., Azure DevOps, Jira, Confluence) to manage work and track delivery. Skills & Requirements Qualifications: + 8+ years of experience in program or project management within a software development environment. + 3+ years specifically leading Agile Release Trains or large-scale agile programs, preferably in a SAFe environment. + SAFe RTE certification (or equivalent practical experience leading ARTs). + Strong knowledge of agile frameworks (Scrum, Kanban, SAFe) and the ability to pragmatically apply them across varying team contexts. + Demonstrated success in facilitating complex planning efforts and delivering large, multi-team initiatives. + Exceptional communication, facilitation, and stakeholder management skills. + Experience with agile planning tools such as Azure DevOps, Jira, Aha!, or similar platforms. Nice to Have + Experience mentoring or coaching others in agile roles (e.g., Scrum Masters, Product Owners). + Experience with digital transformation or agile maturity assessments.• + Familiarity with DevOps practices and the intersection of agile and continuous delivery.