Controller (AI-Driven) — Remote + Equity

Trust & Will; Maryland City (MD); 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 reimbursement

Work from home stipend

Job summary

Trust & Will, a remote-first digital estate planning platform, seeks a Controller to steer financial operations during growth. You will oversee month-end close, tax compliance, and vendor management while driving internal controls and automation with AI.

Lead a high-growth accounting team and collaborate with FP&A on strategic cost analysis. The role emphasizes leadership, technical accounting excellence, and the ability to scale processes in a fast-paced environment.

Qualifications

• 10+ years in accounting with 4–5 years in a leadership role.
• CPA preferred; strong track record in financial reporting and controls.
• Experience with AI/automation to optimize accounting workflows.

Responsibilities

• Own accounting for Trust & Will and subsidiaries, month-end close, tax compliance, AP/AR.
• Build and maintain internal controls; scale operations.
• Lead audits and reconciliations; ensure accuracy to the last detail.
• Manage accounting tech stack; partner with FP&A for integrated systems.
• Analyze costs with CFO and FP&A to identify optimization opportunities.
• Oversee vendor relationships and policy compliance.

Skills

Leadership experience

AI/Automation in accounting

Financial reporting

Communication skills

Analytical thinking

Vendor management

IPO readiness

Big 4 background

Startup experience

Education

CPA certification

Tools

Rillet

Ramp

Google Sheets

Excel

Job description

Trust & Will, a remote-first digital estate planning platform, seeks a Controller to steer financial operations during growth. You will oversee month-end close, tax compliance, and vendor management while driving internal controls and automation with AI.

Lead a high-growth accounting team and collaborate with FP&A on strategic cost analysis. The role emphasizes leadership, technical accounting excellence, and the ability to scale processes in a fast-paced environment.