Controller: AI-Driven Finance Leader (Remote)

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

Benefits offered by this job

Equity included

Health benefits

401(k) with company match

Learning & development reimbursement

Remote-friendly environment

Job summary

Trust & Will, a remote-first digital estate planning leader, is seeking a Controller to guide financial operations during a growth phase. You will own accounting for Trust & Will and its subsidiaries, manage the month-end close, tax compliance, and payables/receivables, ensuring timely, accurate data.

The role emphasizes internal controls, audits, and optimizing the accounting tech stack with AI-enabled workflows.

Qualifications

• Minimum of 10 years of accounting experience, with at least 4-5 years in a Controller or similar leadership role within a high-growth environment.
• Hands-on experience applying AI or automation to accounting workflows.
• Experience designing internal controls for automated or AI-assisted processes.
• Proficiency in accounting software (Ramp, Rillet) as well as Google Sheets & Excel.
• Familiarity with startups, IPO prep, and financial regulations.

Responsibilities

• Own accounting at Trust & Will and its subsidiaries. Manage month-end close, tax compliance, and AP/AR.
• Develop and maintain internal controls to safeguard assets and scale operations.
• Lead audits and reconciliations to ensure accuracy.

Skills

Leadership

AI/Automation

Financial reporting

Communication

Analytical thinking

Education

CPA certification

Tools

Ramp

Rillet

Job description

Trust & Will, a remote-first digital estate planning leader, is seeking a Controller to guide financial operations during a growth phase. You will own accounting for Trust & Will and its subsidiaries, manage the month-end close, tax compliance, and payables/receivables, ensuring timely, accurate data.

The role emphasizes internal controls, audits, and optimizing the accounting tech stack with AI-enabled workflows.