Remote-First Controller: AI-Driven Accounting Leader

Trust & Will; Montpelier (VT); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

Equity package

Health benefits

401(k) with company match

Flexible work schedule

Remote-first company

Learning & development reimbursement

Work from home stipend

Job summary

Trust & Will is seeking a seasoned Controller to own accounting operations, controls, and the evolution of our financial systems in a remote-first, fast‑growing company.

Reporting to the CFO, you will lead month‑end closes, tax compliance, audits, and cost analysis while partnering with FP&A to drive strategic planning and scalable processes. We offer a salary range and equity as part of a comprehensive package.

Qualifications

• 10+ years accounting experience with 4–5 years in a Controller/leadership role.
• Experience with financial reporting, compliance, and internal controls.
• Hands-on AI/automation experience in accounting workflows.
• CPA preferred; familiarity with startups and IPO prep.
• Proven capability to develop and manage direct reports.

Responsibilities

• Own accounting operations for Trust & Will and subsidiaries.
• Lead month-end close, tax compliance, A/P and A/R.
• Develop internal controls and oversee audits and reconciliations.
• Manage accounting tech stack and collaborate with FP&A.
• Partner with CFO on financial strategy and cost optimization.
• Oversee vendor management and policy compliance.

Skills

Accounting leadership

AI automation

Communication

Analytical mindset

Adaptability

Startup experience

Big 4 experience

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

LLM tools

Job description

Trust & Will is seeking a seasoned Controller to own accounting operations, controls, and the evolution of our financial systems in a remote-first, fast‑growing company.

Reporting to the CFO, you will lead month‑end closes, tax compliance, audits, and cost analysis while partnering with FP&A to drive strategic planning and scalable processes. We offer a salary range and equity as part of a comprehensive package.