Controller - AI-Driven Finance Leader (Remote)

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

Benefits offered by this job

Salary + Equity

PTO and holidays

Health benefits, dental and vision

401(k) with company match

Menta health support

Learning & development reimbursement

Remote-friendly with flexible schedule

Work from home stipend

Job summary

Trust & Will, a remote-first digital estate planning platform, is seeking a Controller to lead accounting operations, internal controls, and financial strategy across the company and its subsidiaries. You will drive month-end close, tax compliance, and optimize technology stacks with FP&A collaboration.

Ideal candidates bring 10+ years in accounting with leadership experience, CPA preferred, and a track record in high-growth environments, including AI-enabled finance workflows and startup

Qualifications

• 10+ years accounting experience, with at least 4–5 years in a Controller or leadership role in a high-growth environment.
• CPA certification is preferred.
• Proven track record in financial reporting, compliance, and implementing financial controls.
• Hands-on experience applying AI or automation to accounting workflows.
• Experience designing internal controls for automated or AI-assisted processes.
• Proficiency in Ramp and Rillet as well as Google Sheets & Excel.
• Familiarity with startup financing, IPO preparation, and regulatory requirements.
• Proven experience managing and developing direct reports.
• Excellent communication and interpersonal skills, capable of explaining complex financial information to non-finance stakeholders.
• Strong analytical skills with a strategic mindset to support business decisions.

Responsibilities

• Own accounting at Trust & Will and its subsidiaries; manage month-end close, tax compliance, and accounts payable/receivable.
• Develop and maintain internal controls to safeguard assets and scale operations.
• Lead audits and ensure accuracy of accounts down to the last detail.
• Manage and optimize the accounting tech stack; coordinate with FP&A for integrated systems.
• Partner with the CFO on cost analysis and financial planning with FP&A support.
• Oversee vendor relationships and ensure compliance with company policies.

Skills

Leadership

Analytical thinking

Communication

AI/Automation mindset

Strategic mindset

Education

CPA preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first digital estate planning platform, is seeking a Controller to lead accounting operations, internal controls, and financial strategy across the company and its subsidiaries. You will drive month-end close, tax compliance, and optimize technology stacks with FP&A collaboration.

Ideal candidates bring 10+ years in accounting with leadership experience, CPA preferred, and a track record in high-growth environments, including AI-enabled finance workflows and startup