AI-Driven Controller — Remote + Equity

Trust & Will; Clayton (NC); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary plus equity

Paid time off

Health benefits

401(k) with company match

Learning & development reimbursement

Remote-friendly culture

Work from home stipend

Job summary

Trust & Will, a remote-first digital estate planning platform, seeks a seasoned Controller to lead accounting for the company and its subsidiaries. You will drive month-end close, tax compliance, and the AP/AR cycles while building scalable controls and a robust tech stack.

You’ll partner with FP&A on cost analysis and strategic planning to support rapid growth. The role requires 10+ years in accounting with 4–5 years in leadership, CPA preferred, and a track record of implementing AI-enabled

Qualifications

• Minimum of 10 years of accounting experience, with at least 4-5 years in a Controller or similar leadership role within a high-growth environment.
• Proven track record in financial reporting, compliance, and implementing financial controls.
• Hands-on experience applying AI or automation (e.g., LLM tools, reconciliation or close-management software, scripting) to accounting workflows.
• Experience designing internal controls for automated or AI-assisted processes.
• Proficiency in accounting software (e.g., Ramp, Rillet) as well as Google Sheets & Excel.
• Familiarity with financial regulations and reporting requirements, particularly those relevant to startups and IPO preparation.
• 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, able to contribute to business strategy and support decision-making processes.

Responsibilities

• Own accounting at Trust & Will and its subsidiaries; manage the month-end closing cycle, tax compliance, and accounts payable/receivable.
• Develop and maintain internal controls that keep us on track, safeguard assets, and position us to scale our operations.
• Lead audits and keep our accounts in check, ensuring accuracy down to the last detail.
• Manage and optimize our accounting tech stack; work closely with FP&A to keep our financial systems running, fully integrated, and efficient.
• Partner with the CFO on financial strategy and planning, and work closely with FP&A to analyze costs and expenditures to identify opportunities.
• Oversee vendor relationships and manage compliance with company policies.

Skills

Leadership

AI automation

Analytical thinking

Strong communicator

Adaptability

Big 4 experience

Education

CPA certification

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will, a remote-first digital estate planning platform, seeks a seasoned Controller to lead accounting for the company and its subsidiaries. You will drive month-end close, tax compliance, and the AP/AR cycles while building scalable controls and a robust tech stack.

You’ll partner with FP&A on cost analysis and strategic planning to support rapid growth. The role requires 10+ years in accounting with 4–5 years in leadership, CPA preferred, and a track record of implementing AI-enabled