AI-Driven Controller — Remote + Equity

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

Benefits offered by this job

Salary + Equity

Employee equity package

PTO and flexible time off

Generous holidays and breaks

Health, dental, vision, life and short

Mental health support with Spring/One

401(k) with company match up to 4%

Learning & development reimbursement

Work from home stipend + Apple gear

Job summary

Trust & Will is a remote-first, fast-growing digital estate planning platform seeking a Controller to lead accounting for the company and its subsidiaries. You will own the month-end close, tax compliance, and AP/AR, while shaping internal controls and the tech stack used by finance.

You will partner with the CFO and FP&A to analyze costs, drive automation, and scale processes. A CPA is preferred, with 10+ years in accounting and leadership in startups or high-growth settings.

Qualifications

• 10+ years in accounting with 4–5 years in a Controller role in a high-growth environment.
• CPA certification preferred; strong track record in financial reporting and controls.
• Experience applying AI/automation in accounting workflows (LLMs, scripting, etc.).
• Proficiency with Ramp, Rillet, Google Sheets and Excel.

Responsibilities

• Own accounting for Trust & Will and its subsidiaries; manage month-end close, tax compliance, and AP/AR.
• Develop and maintain internal controls to scale operations.
• Lead audits and reconciliations with high accuracy.
• Manage accounting technology stack and integrate with FP&A.

Skills

Leadership in accounting

AI in accounting

Communication

Analytical mindset

Adaptable to fast-paced environments

Education

CPA preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will is a remote-first, fast-growing digital estate planning platform seeking a Controller to lead accounting for the company and its subsidiaries. You will own the month-end close, tax compliance, and AP/AR, while shaping internal controls and the tech stack used by finance.

You will partner with the CFO and FP&A to analyze costs, drive automation, and scale processes. A CPA is preferred, with 10+ years in accounting and leadership in startups or high-growth settings.