Remote AI-Driven Controller for High-Growth Finances

Trust & Will; Pennsylvania; Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

Flexible time off

Generous holidays

Friends & family day

Volunteer time off

Medical/dental/vision insurance

Mental health support

401(k) with company match

Flexible schedule

Remote-friendly environment

Learning & development reimbursement

Work from home stipend + Apple gear

Job summary

Trust & Will is seeking a senior Controller to lead accounting across the company and its subsidiaries. You will own the close cycle, tax compliance, internal controls, and the evolving finance tech stack, partnering closely with FP&A and the CFO.

You should bring 10+ years in accounting, including leadership in high-growth environments, with CPA preferred, and a proven ability to implement AI-driven automation and strong governance.

Qualifications

• 10+ years in accounting with 4–5 years in a controller/leadership role in high-growth startups.
• CPA preferred; experience with financial reporting, compliance, and internal controls.
• Hands-on use of AI/automation to streamline close processes.
• Experience designing controls for automated or AI-assisted workflows.

Responsibilities

• Own accounting for Trust & Will and subsidiaries; manage month-end close, tax compliance, AP/AR.
• Develop and maintain internal controls to scale operations and safeguard assets.
• Lead audits and reconciliations with accuracy and timeliness.
• Oversee accounting tech stack; collaborate with FP&A to keep systems integrated.

Skills

AI & automation in accounting

Leadership experience

Communication skills

Analytical thinking

Adaptability

Education

CPA preferred

Tools

Ramp

Rillet

Google Sheets

Excel

LLM tooling

Job description

Trust & Will is seeking a senior Controller to lead accounting across the company and its subsidiaries. You will own the close cycle, tax compliance, internal controls, and the evolving finance tech stack, partnering closely with FP&A and the CFO.

You should bring 10+ years in accounting, including leadership in high-growth environments, with CPA preferred, and a proven ability to implement AI-driven automation and strong governance.