Director, Enterprise Program Management

Director, Enterprise Program Management

This is a high-visibility, enterprise-level leadership role responsible for driving the success of a complex, multi-workstream customer implementation at scale. You will own the end-to-end delivery of a strategic program spanning onboarding, configuration, training, data migration, integrations, and rollout across a large multi-location environment.

Accountabilities

• Own end-to-end program delivery for a strategic enterprise customer, from kickoff through go-live and post-launch phases, ensuring alignment on scope, timeline, and success criteria.
• Lead governance across all program workstreams including onboarding, configuration, training, data migration, integrations, rollout execution, and post-launch support.
• Serve as the primary executive point of contact for the customer, managing stakeholder alignment, expectation setting, and resolution of complex or ambiguous issues.
• Chair weekly program stand‐ups, steering committee meetings, and executive reviews, ensuring clear visibility into progress, risks, and dependencies.
• Maintain and actively manage program risk registers, proactively identifying issues and driving mitigation strategies across internal and external teams.
• Lead and coordinate cross‐functional delivery teams across implementation, customer success, training, support, product, and engineering stakeholders.
• Ensure accountability for milestone delivery, including successful multi‐office go‐live, user enablement, integration validation, and transition into Phase II.
• Define and track program success metrics, including adoption, operational readiness, and customer health indicators through post‐go‐live phases.
• Oversee resource planning and execution to ensure delivery capacity aligns with aggressive timelines and scaling demands.
• Position the engagement for long‐term expansion and successful transition into broader enterprise deployment phases.

Requirements

• 10+ years of experience leading complex enterprise SaaS implementations, professional services programs, or customer success delivery functions with program-level accountability.
• Proven experience managing large-scale, multi-location deployments (100+ sites or equivalent) with tight timelines and senior executive stakeholders.
• Strong expertise in program governance, including risk management, dependency tracking, milestone reporting, and executive-level communication.
• Demonstrated ability to lead cross‐functional teams across implementation, customer success, training, and support functions with full accountability for outcomes.
• Exceptional stakeholder management skills, with experience engaging and influencing senior customer executives in high-pressure environments.
• Strong problem-solving skills with the ability to operate effectively in ambiguity and make sound decisions under pressure.
• Excellent written and verbal communication skills, with the ability to adapt messaging between executive steering committees and operational delivery teams.
• Preferred: experience in accounting, professional services, or practice management software environments, or familiarity with multi‐tenant SaaS deployment models.
• Preferred: experience working with large enterprise rollouts involving integrations and complex organizational structures such as franchise or multi-office networks.

Benefits

• Competitive base salary range of $220,000 – $250,000 USD
• Equity eligibility as part of total compensation package
• Fully remote work flexibility across the United States
• Comprehensive health, dental, and vision insurance with employer contributions
• 401(k) retirement plan with company matching
• Flexible time off policy with an encouraged 4-week minimum usage
• Paid parental leave (up to 8 weeks)
• Home office stipend to support remote work setup
• Flexible spending account (FSA) options
• Strong emphasis on learning, development, and internal career progression
• Inclusive, collaborative, and globally distributed work culture