AI-Driven Controller & Finance Strategy Leader (Remote)

Trust & Will; Maryland City (MD); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

Generous PTO

Comprehensive health benefits

401(k) with company match

Learning & development reimbursement

Work from home stipend

Job summary

Trust & Will is a remote-first digital estate planning platform seeking a senior Controller to oversee accounting operations, controls, audits, and system optimizations across the company and its subsidiaries.

Reporting to the CFO, you will lead a fast-growing finance team, drive AI-enabled automation in closing and reporting, and partner with FP&A to shape financial strategy while ensuring regulatory compliance and scalable processes.

Qualifications

• Minimum of 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 is preferred; experience with AI/automation in accounting workflows is a plus.
• Proficiency in Ramp, Rillet, Google Sheets and Excel.

Responsibilities

• Own accounting operations for Trust & Will and subsidiaries; manage month-end close, tax compliance, and AP/AR.
• Develop and maintain internal controls to scale operations and safeguard assets.
• Lead audits and reconciliations with accuracy and timeliness.
• Manage accounting technology stack; collaborate with FP&A to keep systems integrated.
• Partner with CFO on cost analysis and budgeting; drive cost optimization.
• Oversee vendor relationships and ensure policy compliance.

Skills

Accounting leadership

AI-enabled accounting

Communicative leadership

Analytical mindset

Adaptable

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 oversee accounting operations, controls, audits, and system optimizations across the company and its subsidiaries.

Reporting to the CFO, you will lead a fast-growing finance team, drive AI-enabled automation in closing and reporting, and partner with FP&A to shape financial strategy while ensuring regulatory compliance and scalable processes.