Remote AI-Driven Controller for Growth-Phase Finances

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

Benefits offered by this job

Salary + Equity

Health benefits + 401(k) with company

Learning & development reimbursement

Flexible work schedule

Job summary

Trust & Will, a remote-first, US-based leader in digital estate planning, seeks a seasoned Controller to steer financial operations amid growth. You will own the accounting for Trust & Will and subsidiaries, drive month-end close, tax compliance, and vendor management while building scalable controls and processes.

You will lead an experienced team, implement AI-driven automation, and partner with FP&A to optimize costs and strategic planning in a fast-paced environment with a strong emphasis on

Qualifications

• 10+ years of accounting experience with 4–5 years in a Controller or leadership role in high-growth environments.
• CPA certification is preferred.
• Hands-on experience applying AI or automation to accounting workflows.
• Experience designing internal controls for automated or AI-assisted processes.

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 enable scale.
• Lead audits and ensure exactness of accounts down to the last detail.
• Manage and optimize the accounting tech stack; collaborate with FP&A on systems integration.

Skills

Leadership

AI automation

Communication

Analytical thinking

Adaptability

Education

CPA preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first, US-based leader in digital estate planning, seeks a seasoned Controller to steer financial operations amid growth. You will own the accounting for Trust & Will and subsidiaries, drive month-end close, tax compliance, and vendor management while building scalable controls and processes.

You will lead an experienced team, implement AI-driven automation, and partner with FP&A to optimize costs and strategic planning in a fast-paced environment with a strong emphasis on