AI-Driven Controller for Fast-Growth Platform

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

Benefits offered by this job

Compensation: Salary + Equity

PTO and holidays

Health benefits and wellness stipend

Flexible schedule

Job summary

Trust & Will is a remote-first digital estate planning platform seeking a Controller to lead accounting across the company and its subsidiaries. You will own the month-end close, tax compliance, and AP/AR while building scalable internal controls as the business grows.

You will lead the accounting team, collaborate with FP&A, and implement AI-driven automation to streamline workflows while ensuring accurate financial reporting and regulatory compliance across the US.

Qualifications

• 10+ years of accounting experience with leadership in a high-growth environment.
• CPA certification preferred; strong financial reporting background.
• Hands-on use of AI/automation in accounting workflows.
• Experience designing internal controls for automated processes.

Responsibilities

• Own accounting operations for Trust & Will and subsidiaries.
• Manage month-end close, tax compliance, and AP/AR.
• Develop and maintain internal controls for scale.
• Lead audits and reconciliations with accuracy.
• Manage accounting tech stack; collaborate with FP&A.
• Cost analysis and optimization with CFO and FP&A.
• Vendor management and policy compliance.

Skills

Leadership

AI automation

Financial analysis

Communication

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will is a remote-first digital estate planning platform seeking a Controller to lead accounting across the company and its subsidiaries. You will own the month-end close, tax compliance, and AP/AR while building scalable internal controls as the business grows.

You will lead the accounting team, collaborate with FP&A, and implement AI-driven automation to streamline workflows while ensuring accurate financial reporting and regulatory compliance across the US.