Chief of Staff, Strategy & PMO Leader

Cornerstone Practice Management LLC; Annapolis (MD); On-site; USD 140,000 - 210,000; Full time

Benefits offered by this job

Health/Dental/Vison insurance

PTO

401K

Breakfast/Lunch provided daily

Job summary

Frost Law in Annapolis seeks a Chief of Staff to operationalize the COO’s priorities. You will own the initiative portfolio end to end, drive PMO standards, and coordinate across HR, technology, operations, and strategy to deliver measurable impact.

Key responsibilities include shaping the strategic initiative pipeline, implementing tech and AI-enabled solutions, and building adoption plans with clear metrics. Strong communication and consulting background required.

Qualifications

• Experience in management consulting (strategy, operations, or technology).
• Proven ownership of end-to-end initiatives from problem definition to adoption.
• Track record leading at least one technology implementation through adoption.
• Strong analytical and quantitative skills for business-case rigor.
• Executive-grade written and visual communication abilities.

Responsibilities

• Lead strategic initiative & PMO leadership for the COO’s portfolio with charters, milestones, and status reporting.
• Map and optimize workflows across processes like intake, billing, and HR to improve utilization and cost.
• Oversee technology implementation, vendor coordination, and adoption tracking.
• Design change management plans, stakeholder maps, and training to ensure uptake.
• Produce decision-ready analyses, business cases, market scans, and financial models.
• Maintain an operating cadence with leadership through weekly reviews and dashboards.

Skills

Strategy execution

End-to-end initiative ownership

Analytical reasoning

Executive communication

Change management

Technology implementation

PMO leadership

Tools

Clio

HubSpot

Generative AI tools

EOS (Operating System)

Job description

Frost Law in Annapolis seeks a Chief of Staff to operationalize the COO’s priorities. You will own the initiative portfolio end to end, drive PMO standards, and coordinate across HR, technology, operations, and strategy to deliver measurable impact.

Key responsibilities include shaping the strategic initiative pipeline, implementing tech and AI-enabled solutions, and building adoption plans with clear metrics. Strong communication and consulting background required.