Director, Project Management

Compliance Holdings•Pikesville, MD

3d•Remote

About The Position

Lumelight is an integrated workplace administration and compliance business. We serve the brokers and third-party administrators who support employers in the complex, crucial areas of benefits design, compliance and administration. We handle the complexities of benefits compliance and administration, empowering you to focus on what you do best. We are hiring for an Director, Project Management: The Director, Project Management is ClearFile’s strategic operational partner and is responsible for converting ClearFile's growth strategy into disciplined execution. This executive will lead the transition from a founder-dependent consulting model to a scalable, technology-enabled regulatory operations platform with repeatable delivery, strong client retention, improved margins, and clear accountability across the organization. The Director will initially perform selected responsibilities, including enterprise prioritization, executive follow-through, and management of strategic initiatives.

Requirements

15+ years of progressive leadership experience in healthcare payer operations, regulatory consulting, professional services, managed services, health technology, or a closely related field.
Demonstrated success owning operations, client delivery, transformation programs, and financial performance in a growth-stage or entrepreneurial environment.
Strong knowledge of healthcare payers, regulatory operations, compliance, project delivery, and technology-enabled services preferred.
Executive-level financial acumen, including budgeting, forecasting, pricing, margin management, capacity planning, and P&L accountability.
Ability to operate strategically while remaining hands-on, decisive, and highly accountable during a period of rapid change.
Executive presence and sound judgment
Ability to create clarity, trust, and accountability across a growing organization.
Strong written and verbal communication
Systems thinking and operational discipline
Client orientation and financial rigor
Talent development, change leadership, technology fluency

Responsibilities

Translate the three- to five-year company strategy into annual operating plans, quarterly priorities, measurable objectives, and accountable owners.
Partner with the CEO on organizational design, capital allocation, pricing, service expansion, technology investment, and market-entry decisions.
Establish an executive operating cadence, including leadership meetings, KPI reviews, risk escalation, and decision tracking.
Lead major cross-functional initiatives scheduled for implementation between August 2026 and January 2027, including the new 2027 operating model and P&L budget.
Own end-to-end delivery across ClearFile's regulatory filing, licensing, compliance, project management, and managed-portfolio.
Build a scalable PMO with consistent intake, scoping, staffing, scheduling, quality assurance, escalation, and client standards.
Implement capacity planning, utilization, project profitability, delivery forecasting, and resource-allocation disciplines.
Standardize workflows across U.S. and offshore teams while preserving high-quality, client-specific regulatory expertise.
Serve as executive sponsor for strategic accounts and ensure early intervention on delivery, relationship, or financial risks.
Partner with business development on solution design, pricing, proposals, implementation, and readiness for new sales.
Increase recurring revenue through standardized managed-service offerings, annual retainers, and cross-selling across health plan, PBM, TPA, and adjacent markets.
Lead adoption of AI-assisted filing workflows, knowledge management, project automation, CRM discipline, and regulatory tools.
Identify work that should be automated, standardized, centralized, outsourced, or discontinued.
Partner with technology resources to develop ClearFile's long-term regulatory operations platform and supporting data architecture.
Build and develop the next level of leadership across operations, client services, project management, regulatory delivery, and business support.
Implement performance management, role clarity, succession planning, professional development, onboarding, and workforce planning.
Create an accountable, collaborative culture that can scale from a specialized consulting organization into a national healthcare services and technology company.
Launch a standardized PMO and client-success operating model across all major engagements.
Improve visibility into project margin, capacity, utilization, revenue forecasting, and account risk.
Reduce CEO dependency for daily operations, issue resolution.
Implement an initial AI and workflow-automation roadmap tied to measurable productivity and margin improvements.