Controller - AI-Driven Finance Leader (Remote + Equity)

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

Benefits offered by this job

Salary + Equity

PTO & Holidays

Health Benefits

Remote work

Learning & Development

Work from home stipend

Job summary

Trust & Will is seeking a seasoned Controller to lead accounting operations, drive internal controls, and scale finance as the company grows. You will oversee month-end close, audits, and the integration of AI-enabled workflows with the finance tech stack.

The role requires 10+ years in accounting, 4–5 years in leadership, and a CPA is preferred. Remote-first company with strong benefits and equity, open to many US states including VT.

Qualifications

• Minimum of 10 years of accounting experience, with at least 4–5 years in a Controller or similar 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 regulations for startups and IPO preparation.
• Proven experience managing and developing direct reports.
• Excellent communication and interpersonal skills for cross-functional stakeholders.
• This position is available to candidates residing in CA, CO, FL, GA, ID, IL, MD, NJ, NY, NC, PA, TX, VT, NV, UT.

Responsibilities

• Own accounting operations for Trust & Will and subsidiaries; manage month-end close, tax compliance, AP/AR.
• Develop and maintain internal controls to safeguard assets and scale operations.
• Lead audits and reconciliations to ensure accuracy.
• Manage and optimize accounting tech stack; collaborate with FP&A for integrated systems.
• Partner with CFO on cost analysis and strategic planning with FP&A.
• Oversee vendor relationships and ensure policy-compliant processes.

Skills

Dynamic leadership

AI automation

Communication

Analytical thinking

Adaptability

Education

CPA preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will is seeking a seasoned Controller to lead accounting operations, drive internal controls, and scale finance as the company grows. You will oversee month-end close, audits, and the integration of AI-enabled workflows with the finance tech stack.

The role requires 10+ years in accounting, 4–5 years in leadership, and a CPA is preferred. Remote-first company with strong benefits and equity, open to many US states including VT.