AI-Driven Controller for Growth & Automation

Trust & Will; Montpelier (VT); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

Remote-friendly environment

Learning & development reimbursement

Work from home stipend

Job summary

Trust & Will, a remote-first digital estate planning company, seeks a Controller to lead accounting operations and internal controls while scaling with growth. You will oversee month-end closes, audits, vendor management, and systems integration in collaboration with FP&A and the CFO.

The role requires 10+ years in accounting, 4–5 in leadership, and a CPA is preferred. Strong communication and analytical skills are essential in a fast-paced environment with equity compensation.

Qualifications

• 10+ years in accounting with 4–5 years in a controller/leadership role in a high-growth setting.
• CPA certification preferred and strong track record in financial reporting and controls.
• Hands-on AI/automation in accounting workflows and automated close processes.

Responsibilities

• Own accounting for Trust & Will and subsidiaries; manage month-end close and tax compliance.
• Develop internal controls and lead audits to ensure accuracy and compliance.
• Oversee accounting tech stack; collaborate with FP&A to keep systems integrated.
• Analyze costs with CFO and FP&A to identify opportunities and optimize spend.
• Manage vendor relationships and ensure policy compliance.

Skills

AI/automation

Leadership

Communication

Analytical

Adaptable

Big 4 experience

Education

CPA

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first digital estate planning company, seeks a Controller to lead accounting operations and internal controls while scaling with growth. You will oversee month-end closes, audits, vendor management, and systems integration in collaboration with FP&A and the CFO.

The role requires 10+ years in accounting, 4–5 in leadership, and a CPA is preferred. Strong communication and analytical skills are essential in a fast-paced environment with equity compensation.