Controller

Company Overview:
Stouffer Legal is a woman-owned Estate Planning firm based in Maryland, preparing for and exciting phase of expansion. As our footprint, team, and operational complexity increase, we are investing in experienced financial leadership to strengthen our forecasting, improve margins, and support responsible, data-backed growth.

We value clarity, discipline, and proactive decision-making, and we are building the financial systems and leadership capacity to match our ambitions.

Position Overview:

We are seeking an experienced Controller to provide hands-on financial leadership and strategic insights as the firm continues to scale.

The Controller's primary responsibility is to ensure strong financial visibility and predictability, particularly around cash flow, margins, and timing, so leadership can make informed decisions with confidence. This role blends technical accounting expertise with forward-looking analysis, systems ownership, and close partnership with leadership. The Controller sits above the firm's three Accounting Managers (who own AR/collections/payroll, AP/cash operations, and close/reconciliation/reporting respectively) and focuses on balance sheet architecture, forecasting, scenario planning, and cross-functional decision partnership rather than day-to-day transactional execution.

This is a high-impact role for someone who enjoys building structure, improving financial discipline, and translating data into clear recommendations.

Location: Towson, Maryland (preferred in-office; remote considered)

Core Job Duties:

Cash Flow Management and Forecasting

• Build and maintain rolling 13-week cash forecast

• Ensure leadership has reliable daily and weekly cash visibility through the accounting team's reporting rhythms

• Analyze cash inflow and outflow patterns surfaced by the accounting team and translate them into working-capital strategy

• Align hiring and expansion decisions with cash availability and forecasted liquidity

Success looks like:

• Reliable, accurate cash forecasts

• Strong visibility into near-term and mid-term cash needs

• Leadership confidence in cash-related decision-making

Financial Reporting and Decision Support

• Review financial reporting produced by the Accounting Manager team and own the analytical narrative, variance commentary, and decision frameworks layered on top

• Translate financial results into clear insights and recommendations for leadership

• Highlight risks, trends, and tradeoffs proactively

• Lead scenario planning (best / base / worst case) and stress-test expansion, hiring, and investment assumptions

• Own balance sheet structure, working-capital targets, operating-reserve policy, and owner-distribution planning

Success looks like:

• Leadership can confidently answer:

• What is happening

• Why it is happening

• What decision should be made as a result

• Variances, trends, and risks are surfaced proactively, not discovered after the fact

• Leadership is able to understand the impact of decisions before they are made

Margin and Performance Analysis

• Develop visibility into contribution margins by office, service line, and referral source

• Identify cost drivers, pricing opportunities, and efficiency improvements

• Architect the annual budget and rolling-forecast model, and partner with the Accounting Manager team who owns budget-vs-actual tracking and variance surfacing

• Partner with AR leadership to analyze structural revenue-cycle trends (write-offs, refunds, payment-plan performance) and convert them into pricing, policy, and collections decisions

Success looks like:

• Leadership understands what is driving margin changes month over month

• Budgeting and forecasting are tied to realistic demand, staffing, and capacity assumptions

• Margin improvement efforts are data-backed and measurable over time

Multi-Location Financial Oversight

• Build scalable financial models and reporting for new and existing offices

• Develop standardized location-level P&Ls and ramp models

• Support expansion planning with data-backed projections

Systems, Controls, and Process Improvement

• Own financial systems and data integrity

• Set the systems roadmap that reduces the accounting team's reliance on spreadsheets and manual reconciliations

• Improve system integrations and reporting automation

• Establish and maintain internal controls and financial standards

Finance Team Leadership and Oversight

• Review month-end close outputs with the Accounting Manager responsible for close to validate materiality, accuracy of narrative, and strategic relevance (close execution is owned by the accounting team)

• Escalate structural AP and AR trends surfaced by the Accounting Manager team into leadership decisions and policy changes

• Ensure trust accounting controls are functioning through periodic review and compliance oversight (IOLTA reconciliations executed by the accounting team)

• Coach, prioritize, and develop members of the finance team

• Identify and eliminate inefficiencies in finance workflows

Leadership Partnership and External Coordination

• Serve as a thought partner to leadership on financial matters

• Support strategic planning and compliance readiness

• Coordinate with banks, auditors, CPAs, and other external partners

• Oversee payroll and benefits audits and compliance posture (payroll and benefits operations are owned by the Accounting Manager team)

• Monitor tax liabilities and support tax planning

Strategic Finance and Cross-Functional Partnership

• Build financial business cases for new offices, major hires, marketing investments, pricing changes, and capital expenditures

• Partner with operations, marketing, and practice leaders to translate business strategy into financial targets, unit economics, and capacity models

• Develop and maintain a long-range (3–5 year) financial model aligned with the firm's growth ambitions

• Define and govern the KPI architecture used across the firm, ensuring finance and operating metrics reconcile and tell a coherent story

• Serve as the finance point of contact for intercompany matters across Stouffer Legal, Callow Consulting, and other affiliated entities

Preferred Qualifications:

• 8 - 15 years of accounting and finance experience

• 3 - 7 years of experience leading and managing a finance team

• Strong ownership of month-end close, budgeting, forecasting, and cash management

• Experience in professional services and multi-location environments

• Experience with multi-entity and multi-state operations

• CPA strongly preferred

• Proven ability to build, improve, and scale finance processes

Career Path:

This role offers meaningful growth potential and may evolve into a Head of Finance or CFO role as the organization continues to scale.

Why Join Us:

At Stouffer Legal, we are more than a law firm-we are a mission-driven team dedicated to protecting families and preserving legacies. As our Controller, you will help steward the firm's financial health so we can serve clients with confidence and care. Through strong forecasting, clear reporting, and disciplined financial leadership, you'll help ensure the stability that allows our mission to thrive.

• High-impact role with direct exposure to leadership

• Opportunity to shape financial systems during a key growth phase

• Collaborative leadership team that values data-driven decisions

• Ability to build structure, discipline, and clarity across the organization

Compensation & Benefits:

• Salary range: $160,000 - $200,000

• Competitive benefits package

• Performance-based incentives aligned with company success

• Health Insurance (CareFirst) with 50% company contribution

• Dental and Vision Insurance

• Company-paid Short-term and Long-term Disability Insurance

• Company-paid Group-Term Life Insurance

• 401(k) with a match of 3%, plus 50% of the next 2%, totaling a 4% employer match, immediate vesting

• Generous PTO (Paid Time Off) starting at 20 days annually, scaling with tenure

• 7 paid holidays per year

• 3 weeks of paid parental leave

Application Process:

1. Application Submission and Screening

2. Initial Phone Screening Interview (15 minutes)

3. Virtual Interview (Microsoft Teams; 30 minutes)

4. Candidate Assessments (Skills and Cultural Fit)

5. In-Person Interview at Towson Office (1 hour; includes office tour)

6. Job Offer and Reference/Background Checks

7. Orientation and Onboarding

Salary : $160,000 - $200,000