Controller - AI-Driven Finance Leader (Remote) with Equity

Trust & Will; Tallahassee (FL); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Equity compensation

Flexible work schedule

Generous holiday time and PTO

Learning & development reimbursement (

Annual work-from-home stipend

Job summary

Trust & Will, a remote-first estate planning platform, seeks a seasoned Controller to lead accounting across the company and its subsidiaries. Reporting to the CFO, you will own month-end close, tax compliance, and internal controls while driving automation and an AI-enhanced finance function in a fast-growing startup environment.

You will build and mentor a high-performing team, partnering with FP&A to analyze costs, manage vendors, and ensure regulatory compliance as the business scales

Qualifications

• Significant accounting leadership in high-growth environments (Controller or similar).
• Experience with financial reporting, compliance, and internal controls.
• Hands-on AI/automation in accounting workflows (LLM tools, scripting).

Responsibilities

• Own accounting at Trust & Will and subsidiaries including month-end close and tax compliance.
• Develop and maintain internal controls to safeguard assets and enable scale.
• Lead audits and ensure accuracy of financial data down to the last detail.
• Manage accounting tech stack and integrate with FP&A for efficiency.
• Partner with CFO on cost analysis and financial strategy with FP&A.
• Oversee vendor relationships and ensure policy compliance.

Skills

Dynamic and Experienced

AI-Native Operator

Communicative Leader

Analytically Inclined

Adaptable

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first estate planning platform, seeks a seasoned Controller to lead accounting across the company and its subsidiaries. Reporting to the CFO, you will own month-end close, tax compliance, and internal controls while driving automation and an AI-enhanced finance function in a fast-growing startup environment.

You will build and mentor a high-performing team, partnering with FP&A to analyze costs, manage vendors, and ensure regulatory compliance as the business scales