AI-Driven Controller — Remote, High-Growth Startup

Trust & Will; Annapolis (MD); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

Health benefits

401(k) with company match

Remote-friendly / Flexible schedule

Learning & development reimbursement

Work from home stipend

Company events/travel

Job summary

Trust & Will, a remote-first digital estate planning leader, seeks a Controller to drive financial operations as the company scales. Reporting to the CFO, you will own accounting across subsidiaries, elevate internal controls, and partner with FP&A on cost analysis and strategic planning.

With 10+ years in accounting and 4–5 in leadership, you’ll lead month-end close, tax compliance, audits, and the tech stack (Ramp, Rillet, Excel/Sheets).

Qualifications

• Minimum 10 years of accounting experience with 4–5 years in a Controller role in a high-growth environment.
• CPA certification preferred.
• Proven track record in financial reporting, compliance, and internal controls.
• Hands-on AI/automation experience in accounting workflows.
• Experience designing internal controls for automated or AI-assisted processes.
• Proficiency in Ramp and Rillet; strong Excel/Sheets skills.
• Familiarity with startup and IPO-related reporting requirements.
• Experience managing and developing direct reports.
• Excellent communication and analytical skills.

Responsibilities

• Own accounting operations and month-end close for Trust & Will and subsidiaries.
• Develop and maintain internal controls to safeguard assets and scale operations.
• Lead audits and reconciliations with attention to detail.
• Manage accounting technology stack and integrate with FP&A.
• Partner with CFO and FP&A on cost analysis and strategic planning.
• Oversee vendor relationships and ensure policy compliance.

Skills

Accounting leadership

AI/Automation in accounting

Communication skills

Analytical mindset

Adaptability

Education

CPA certification

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first digital estate planning leader, seeks a Controller to drive financial operations as the company scales. Reporting to the CFO, you will own accounting across subsidiaries, elevate internal controls, and partner with FP&A on cost analysis and strategic planning.

With 10+ years in accounting and 4–5 in leadership, you’ll lead month-end close, tax compliance, audits, and the tech stack (Ramp, Rillet, Excel/Sheets).