Welcome to Frontline Managed Services® – where innovation, technology, and efficiency converge to redefine the landscape of IT, Financial, and Administrative Managed Services for legal and professional service firms. As pioneers in the industry, we are driven by a relentless commitment to excellence.

Position Overview 

The Program Manager, Enterprise Transformation is responsible for leading complex, cross-functional technology and operational initiatives across Frontline Managed Services. The immediate priority of the role is the enterprise migration from ConnectWise and ServiceNow to HaloPSA; however, the role extends beyond a single platform implementation.

This role provides disciplined program and project leadership across strategic initiatives, including data

and reporting architecture, process definition, operational standardization, business-system integrations, and continuous improvement. The position is responsible for organizing ambiguity, driving best practices, aligning business and technical teams, and advancing multiple interdependent initiatives from concept through implementation and measurable business outcomes.

What You’ll Do

Enterprise Transformation & Strategic Initiatives:

·       Serve as the Program Manager for a phased enterprise service management and business operations platform transformation, coordinating workstreams across ITSM, CRM, quote-to-cash, client and contract management, service delivery, billing and financial workflows, platform configuration, data migration, integrations, reporting, testing, training, cutover, hypercare, and legacy-platform retirement.

·       Lead and coordinate phased migrations across multiple business units and operating teams, capturing lessons learned from each phase and applying proven operating models, processes, and delivery approaches to subsequent phases.

·       Manage critical program dependencies including telephony and contact-center technologies, enterprise integrations, data readiness, business process decisions, and operational preparedness, while maintaining alignment with the broader enterprise transformation roadmap.

Stakeholder, Vendor & Change Management:

·       Build alignment across executives, business owners, process owners, technical teams, end users, and external partners by establishing clear responsibilities, commitments, timelines, and communication channels.

·       Manage vendor and implementation-partner deliverables, dependencies, risks, escalations, and accountability while ensuring internal teams remain informed and engaged.

·       Coordinate organizational readiness activities including communications, user acceptance testing, training, adoption, go-live readiness, hypercare, and transition to steady-state support.

Program & Project Leadership:

·       Lead complex enterprise programs and projects from initiation through planning, execution, implementation, stabilization, and transition to operational ownership.

·       Develop and maintain integrated project plans, scope, schedules, milestones, resource requirements, budgets, dependencies, decision logs, action items, and delivery forecasts.

·       Apply consistent project-management standards, tools, governance, documentation, and delivery disciplines while adapting the approach to the size, risk, and complexity of each initiative. 

Governance, Risk & Executive Communication:

·       Establish appropriate governance structures, meeting cadences, status reporting, stage gates, escalation paths, and decision-making forums for assigned programs.

·       Provide clear executive and stakeholder reporting on program health, accomplishments, upcoming milestones, scope, schedule, budget, risks, dependencies, decisions, and required actions.

·       Identify delivery risks and issues early, develop mitigation and recovery plans, clarify ownership, and drive timely resolution across business, technology, and vendor teams. 

Process Definition & Best-Practice Enablement:

·       Facilitate workshops that convert business objectives and operational pain points into clear requirements, decisions, process designs, acceptance criteria, and executable work plans. 

·       Promote practical industry and project management best practices, challenging unnecessary complexity and helping teams standardize, simplify, automate, and continuously improve how work is performed. 

Data, Architecture & Cross-Functional Coordination:

·       Help coordinate the development of Frontline’s enterprise data and reporting architecture, including the future-state Data Warehouse, source-system alignment, data ownership, reporting requirements, dependencies, and delivery sequencing.

·       Work with business, application, data, infrastructure, security, and integration teams to connect architectural decisions to program plans, milestones, dependencies, testing, and operational outcomes.

·       Coordinate cross-functional initiatives involving business systems, integrations, data migration, reporting, analytics, automation, security, finance, CRM, telephony, service-management platforms, and other enterprise technologies. 

What You Bring

Education and Experience:

·       Bachelor’s degree in business, Information Systems, Technology, Project Management, or equivalent practical experience.

·       7+ years of progressive project or program management experience leading complex, cross functional business and technology initiatives.

·       Experience leading enterprise PSA, ITSM, ERP, CRM, data, analytics, or comparable business platform transformation programs.

·       Experience with HaloPSA, ServiceNow, ConnectWise, Autotask, FreshService, or similar enterprise service management platforms.

·       Experience supporting Data Warehouse, business intelligence, reporting, data governance, or enterprise data initiatives.

·       Experience in a managed service, IT services, legal, or professional services environment.

·       Experience managing software vendors, implementation partners, systems integrators, and distributed internal teams.

·       PMP, PgMP, ITIL Foundation, Agile, Scrum, or comparable project/program management certification preferred.

Skills and Abilities

·       Demonstrated ability to manage multiple interdependent workstreams, priorities, stakeholders, schedules, risks, dependencies, and delivery commitments. 

·       Strong knowledge of project and program management disciplines, including: 

o   Scope management

o   Planning and scheduling

o   Budgeting

o   Risk, Assumptions, Issues, and Dependencies (RAID) management

o   Governance

o   Testing and implementation

o   Transition to operations

·       Experience facilitating discovery sessions, requirements gathering, process mapping, future state design, decision-making, and stakeholder alignment workshops. 

·       Experience coordinating business, application, data, architecture, integration, infrastructure, security, and operational teams. 

·       Strong executive communication, facilitation, documentation, negotiation, problem-solving, and change leadership skills. 

·       Working knowledge of ITIL practices and service management.

Not Sure You Meet Every Requirement?

We know that great candidates may not match every qualification listed. If you’re excited about the role and believe you could be a strong fit, we encourage you to apply. We value potential and a growth mindset as much as experience.

Join Us

At Frontline Managed Services, we celebrate different backgrounds, experiences, and perspectives. We are committed to building a team that reflects the clients and communities we serve.

“We are an equal opportunity employer. All applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status.”