Remote Controller | AI-Driven Finance Leader

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

Benefits offered by this job

Salary + Equity

PTO & Holidays

Health benefits

401(k) with company match

Learning & development

Job summary

Trust & Will is a remote-first digital estate planning platform seeking a senior Controller to lead accounting operations, close cycles, and ensure compliance as the company scales.

You will own internal controls, work with FP&A on cost analysis, and drive AI-enabled automation across the finance stack while mentoring the accounting team.

Qualifications include 10+ years in accounting, 4–5 years in leadership, CPA preferred; residency states list includes VT.

Qualifications

• 10+ years of accounting experience with 4–5 years in a Controller or similar leadership role in a high-growth environment.
• CPA certification preferred.
• Hands-on experience applying AI or automation to accounting workflows.
• Experience designing internal controls for automated or AI-assisted processes.

Responsibilities

• Own accounting at Trust & Will and its subsidiaries; manage month-end close, tax compliance, and payables/receivables.
• Develop and maintain internal controls to scale operations.
• Lead audits and reconciliations with an emphasis on accuracy.
• Manage and optimize the accounting technology stack; collaborate with FP&A.
• Partner with CFO on financial strategy and cost analyses; oversee vendor relationships.

Skills

Leadership experience

AI automation

Communication

Analytical thinking

Adaptability

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will is a remote-first digital estate planning platform seeking a senior Controller to lead accounting operations, close cycles, and ensure compliance as the company scales.

You will own internal controls, work with FP&A on cost analysis, and drive AI-enabled automation across the finance stack while mentoring the accounting team.

Qualifications include 10+ years in accounting, 4–5 years in leadership, CPA preferred; residency states list includes VT.