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: $140,000 - $170,000
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