Controller, AI-Driven FinOps Leader (Remote + Equity)

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

Benefits offered by this job

Salary + Equity

PTO

Flexible time off

Company holidays

Health benefits

401(k) with company match

Work from home stipend

Job summary

Trust & Will, a leading digital estate planning platform, is seeking a Controller reporting to the CFO. You will own accounting for the company and subsidiaries, drive month-end close, tax compliance, and internal controls in a high-growth environment.

You will lead the accounting team, implement AI-enabled workflows, and collaborate with FP&A to optimize costs and strategy. This remote-first role supports teams nationwide, with a strong emphasis on governance and scalability.

Qualifications

• 10+ years of accounting experience, with 4–5 years in a Controller or leadership role in a high-growth environment.
• CPA certification preferred.
• Hands-on AI/automation experience in accounting workflows.
• Experience designing internal controls for automated/AI-assisted processes.
• Proficiency with Ramp, Rillet, Google Sheets & Excel.
• Familiarity with startup/IPOs and regulatory reporting.
• Experience managing and developing direct reports.
• Excellent communication for non-finance stakeholders.

Responsibilities

• Own accounting for Trust & Will and subsidiaries, including month-end close and tax compliance.
• Manage accounts payable/receivable and ensure timely financial data.
• Develop and maintain internal controls to scale operations.
• Lead audits and reconciliations with attention to detail.
• Oversee accounting tech stack and coordinate with FP&A.
• Partner with CFO on cost analysis and financial strategy.
• Oversee vendor relationships and policy compliance.

Skills

Accounting leadership

AI/automation in finance

Financial analysis

Communication

Strategic mindset

People management

Adaptability

Education

CPA preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a leading digital estate planning platform, is seeking a Controller reporting to the CFO. You will own accounting for the company and subsidiaries, drive month-end close, tax compliance, and internal controls in a high-growth environment.

You will lead the accounting team, implement AI-enabled workflows, and collaborate with FP&A to optimize costs and strategy. This remote-first role supports teams nationwide, with a strong emphasis on governance and scalability.