Remote Controller - AI-Driven Finance Leader

Trust & Will; Springfield (IL); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Equity included

Remote-first

Paid time off

Professional development

Job summary

Trust & Will, a remote-first estate planning platform, seeks a Controller to lead accounting operations, internal controls, and system improvements across the company and its subsidiaries. The role reports to the CFO and partners with FP&A to scale finance during growth.

The ideal candidate has 10+ years in accounting, with 4–5 years in leadership, CPA preferred, and a track record in financial reporting, governance, and AI-enabled workflows.

Qualifications

• 10+ years accounting experience with 4–5 years in a Controller or leadership role in a high-growth environment.
• CPA certification preferred.
• Experience in financial reporting, compliance, and internal controls.
• Hands-on AI/automation experience in accounting workflows.
• Experience designing internal controls for automated/AI-assisted processes.
• Familiar with Ramp and Rillet and standard spreadsheet tools.

Responsibilities

• Own accounting for Trust & Will and subsidiaries, including month-end close, tax compliance, and accounts payable/receivable.
• Develop and maintain internal controls to safeguard assets and scale operations.
• Lead audits and maintain accurate accounts.
• Manage accounting technology stack and integrate with FP&A.
• Collaborate with CFO and FP&A on cost analysis and financial planning.
• Oversee vendor relationships and ensure policy compliance.

Skills

Leadership experience

AI/Automation in accounting

Communication skills

Analytical mindset

Adaptability

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first estate planning platform, seeks a Controller to lead accounting operations, internal controls, and system improvements across the company and its subsidiaries. The role reports to the CFO and partners with FP&A to scale finance during growth.

The ideal candidate has 10+ years in accounting, with 4–5 years in leadership, CPA preferred, and a track record in financial reporting, governance, and AI-enabled workflows.