AI-Driven Controller | Scale Finance & Compliance

Trust & Will; Maryland; Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

PTO and holidays

Health, dental, vision, life insurance

401(k) with company matching

Learning & development reimbursement

Job summary

Trust & Will, a leading remote-first estate planning platform, seeks a Controller to steer accounting operations, internal controls, and AI-driven automation across the finance stack. You will lead a fast-growing team, shape financial strategy with the CFO, and ensure scalable, compliant processes for a national footprint.

The role emphasizes ERP/AI-enabled workflows, strong leadership, and collaboration with FP&A to optimize costs while guiding growth in a startup-friendly environment.

Qualifications

• Minimum of 10 years accounting experience with at least 4-5 years in a Controller or similar leadership role within a high-growth environment
• CPA certification is preferred; strong track record in financial reporting, compliance and implementing financial controls
• Hands-on experience applying AI or automation (e.g., LLM tools, reconciliation or close-management software, scripting) to accounting workflows
• Experience designing internal controls for automated or AI-assisted processes
• Proficiency in accounting software (e.g., Ramp, Rillet) as well as Google Sheets & Excel
• Familiarity with financial regulations and reporting requirements, particularly startups and IPO preparation

Responsibilities

• Own accounting operations for Trust & Will and its subsidiaries; manage the month-end closing cycle, tax compliance, and accounts payable/receivable
• Develop and maintain internal controls that safeguard assets and enable scaling of operations
• Lead audits and reconciliations to ensure accuracy down to the last detail
• Manage accounting technology stack and collaborate with FP&A to keep systems integrated and efficient
• Partner with the CFO on financial strategy and cost analysis with FP&A to identify optimization opportunities
• Oversee vendor relationships and ensure compliance with company policies

Skills

Leadership experience

AI/automation in accounting

Strong communication

Analytical mindset

Strategic finance

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Scripting for automation

Job description

Trust & Will, a leading remote-first estate planning platform, seeks a Controller to steer accounting operations, internal controls, and AI-driven automation across the finance stack. You will lead a fast-growing team, shape financial strategy with the CFO, and ensure scalable, compliant processes for a national footprint.

The role emphasizes ERP/AI-enabled workflows, strong leadership, and collaboration with FP&A to optimize costs while guiding growth in a startup-friendly environment.