AI-Driven Controller for Growth, Controls & Compliance

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

Benefits offered by this job

Salary + Equity

PTO & holidays

Medical, dental, vision

401(k) match

Learning & development reimbursement

Job summary

Trust & Will, a remote-first digital estate planning platform, seeks a Controller to lead accounting for the company and its subsidiaries. You will own month-end close, controls, audits, and the accounting tech stack, collaborating with FP&A and the CFO on cost analysis and strategic planning.

You should bring 10+ years of accounting experience, (CPA preferred), and a track record of building scalable processes in fast-growing settings. This role offers salary, equity, and strong benefits.

Qualifications

• Minimum 10 years of accounting experience, with at least 4-5 years in a Controller or senior leadership role in a high-growth environment.
• CPA certification preferred.
• Hands-on experience applying AI or automation to accounting workflows.

Responsibilities

• Own accounting operations for Trust & Will and subsidiaries.
• Manage month-end close, tax compliance, and payables/receivables.
• Develop and maintain internal controls to scale operations.
• Lead audits and reconciliations to ensure accuracy.
• Manage accounting tech stack and partner with FP&A to keep systems integrated.
• Partner with CFO on cost analysis and optimize expenditures.

Skills

Leadership

AI/Automation

Communication

Analytical thinking

Adaptability

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first digital estate planning platform, seeks a Controller to lead accounting for the company and its subsidiaries. You will own month-end close, controls, audits, and the accounting tech stack, collaborating with FP&A and the CFO on cost analysis and strategic planning.

You should bring 10+ years of accounting experience, (CPA preferred), and a track record of building scalable processes in fast-growing settings. This role offers salary, equity, and strong benefits.