Chief of Staff

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 is a growing Annapolis-based law firm with more than 40 attorneys, nationally recognized for our work in tax, estate, bankruptcy, and business law.

The Chief of Staff is the COO’s force multiplier: a consulting-trained operator who turns the COO’s priorities into scoped, staffed, and delivered initiatives. The role owns the firm’s strategic initiative portfolio end to end, from problem definition through implementation and adoption, across process improvement, technology, change management, and corporate strategy.

Why this role exists:

The COO’s portfolio has outgrown one person’s execution bandwidth. The COO spans HR, technology, operations, compliance, business development, and strategy, while running multiple concurrent transformation efforts. Without dedicated capacity, initiatives stall between decision and adoption, and the COO’s time goes to coordination instead of judgment.

This role closes that gap. It gives the COO a single owner for initiative delivery, a consistent operating cadence, and decision-ready analysis on demand.

Year-one success looks like:

• A single, prioritized initiative portfolio with owners, milestones, and status visible to leadership at all times
• At least three major initiatives moved from pilot or plan to full adoption, with measured business impact
• Measurable improvement in firm profitability levers the COO owns: utilization, realization, and expense
• The COO reclaims 8 to 10 hours per week from coordination, follow-up, and first-draft work
• Partners and department heads see the Office of the COO as faster and more predictable to work with

Key responsibilities:

The role splits across five workstreams. Time allocations are targets and will flex with the portfolio.

Strategic initiative & PMO leadership

30%

Run the COO’s initiative portfolio: charters, workplans, RACI, milestone tracking, risk and issue logs. Stand up a lightweight PMO standard (intake, prioritization, status reporting) and drive initiatives to closure.

Process improvement & operational excellence

20%

Map current-state workflows in intake, billing, collections, matter management, and HR. Identify bottlenecks and leakage, design future state, and quantify impact on utilization, realization, cycle time, and cost.

Technology implementation & AI enablement

20%

Lead business-side implementation of new systems and AI tools: requirements, vendor coordination, configuration decisions, testing, rollout, and adoption tracking. Act as the bridge between partners, staff, and IT/vendors.

Change management & adoption

15%

Build stakeholder maps, communication plans, training, and feedback loops for every major change. Track adoption metrics and intervene early where uptake lags. Manage partner and practice-group alignment.

Corporate strategy & COO office support

15%

Produce decision-ready analysis: business cases, market and competitive scans, pricing and financial models, board/partner materials. Prepare and run the COO’s operating cadence (leadership meetings, scorecards, follow-ups) and handle confidential special projects.

Initial portfolio and first 90 days

The hire inherits live initiatives on day one.

Likely initial portfolio:

• Ajax AI timekeeping implementation: drive rollout, adoption metrics, and change management
• Firm-wide AI enablement: governance, training program, and use‑case pipeline
• Cornerstone MSO platform repositioning: business case, pricing model, and governance design
• Performance Snapshot redesign: rollout of the quarterly pulse and post‑project snapshots
• Productivity and realization analytics
• Firmwide KPI definition, tracking, and analysis

First 90 days:

• Days 1–30, learn and diagnose: meet every partner and department head; inventory all open initiatives; build the first consolidated portfolio view with status and owners.
• Days 31–60, prioritize and structure: agree the top five priorities with the COO; charter each with scope, success metrics, and owners; install a weekly COO operating rhythm.
• Days 61–90, deliver: land at least one visible win; present a 12‑month initiative roadmap to the COO and other members of the Executive Team.

Qualifications:

Required

• Experience in management consulting (strategy, operations, or technology practice)
• Demonstrated ownership of end‑to‑end initiatives: problem definition, analysis, recommendation, and hands‑on implementation
• Track record leading at least one technology implementation through adoption, not just selection
• Strong analytical skills and can quantify the business case for a change
• Executive‑grade written and visual communication: synthesizes complex issues into a one‑page recommendation or a short deck
• Digs deep to solve for the root cause, not just a symptom of an issue

Preferred

• Post‑consulting operating role (Chief of Staff, strategy and operations, PMO lead) in a professional services, PE‑backed, or multi‑site business
• Exposure to law firm or professional services economics: utilization, realization, leverage, and billing
• Familiarity with practice management and CRM platforms (e.g., Clio, HubSpot) and practical use of generative AI tools
• Experience with EOS or a similar operating system
• MBA or equivalent graduate degree

Benefits:

• Health/Dental/Vison insurance
• PTO
• 401K
• Breakfast/Lunch provided daily