Remote Senior Controller — AI-Driven Finance & Compliance

Trust & Will; Colorado Springs (CO); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

Employee equity package

Flexible work schedule

Work from home stipend

Learning & development reimbursement

Company events and travel

Paid time off

Job summary

Trust & Will is seeking a senior Controller to lead accounting operations, internal controls, and tech stack optimization. The role partners with the CFO and FP&A to drive cost analysis, compliance, and scalable processes in a remote-first, nationwide capacity.

Requirements include 10+ years of accounting experience with 4–5 years in a leadership role, CPA preferred, and hands-on AI/automation work in finance workflows.

Qualifications

• 10+ years accounting experience with 4–5 years in a controller/leadership role in high-growth environments.
• CPA certification preferred.
• Proven track record in financial reporting, compliance, and internal controls.
• Hands-on AI/automation experience in accounting workflows.
• Experience designing internal controls for automated/AI-assisted processes.
• Proficient with Ramp and Rillet; skilled in Google Sheets & Excel.

Responsibilities

• Own accounting at Trust & Will and subsidiaries; manage month-end close and tax compliance.
• Develop and maintain internal controls to safeguard assets and scale operations.
• Lead audits and ensure accuracy of accounts down to the last detail.
• Manage accounting tech stack; collaborate with FP&A for integrated systems.
• Partner with CFO on cost analysis and strategic planning with FP&A.
• Oversee vendor relationships and ensure policy compliance.

Skills

Leadership experience

AI automation

Communication

Analytical thinking

Adaptability

Education

CPA certification

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will is seeking a senior Controller to lead accounting operations, internal controls, and tech stack optimization. The role partners with the CFO and FP&A to drive cost analysis, compliance, and scalable processes in a remote-first, nationwide capacity.

Requirements include 10+ years of accounting experience with 4–5 years in a leadership role, CPA preferred, and hands-on AI/automation work in finance workflows.