Remote Controller — AI-Driven Finance Leader with Equity

Trust & Will; Colorado Springs (CO); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

PTO & Flexible time off

Holiday breaks and wellness programs

Health, dental, vision, life, and long

401(k) with 4% company match

Work from home stipend

Job summary

Trust & Will, a remote-first digital estate planning leader, seeks a Controller to lead accounting across the company and subsidiaries. The role focuses on month-end close, tax compliance, and efficient AP/AR, while building scalable controls and automating processes with AI.

The ideal candidate has 10+ years of accounting experience, 4–5 in a leadership role, and a background in fast-scaling environments. CPA preferred; remote work option with competitive compensation.

Qualifications

• 10+ years of accounting experience, with 4–5 years in a Controller or leadership role.
• Big 4 background plus startup experience is a plus.
• Hands-on in AI/automation applied to accounting workflows.
• Experience designing internal controls for automated/AI-assisted processes.
• Proficiency with Ramp and Rillet; strong Google Sheets & Excel skills.

Responsibilities

• Own accounting at Trust & Will and subsidiaries; manage month-end close; ensure tax compliance and AR/AP.
• Develop and maintain internal controls to safeguard assets and enable scale.
• Lead audits and reconciliations to ensure accuracy.
• Manage accounting technology stack and integrate with FP&A.
• Partner with CFO on cost analysis and financial planning.
• Oversee vendor relationships and ensure policy compliance.

Skills

Leadership

Analytical thinking

Communication

Adaptability

Strategic thinking

AI automation mindset

Education

CPA (preferred)

Tools

Ramp

Rillet

Job description

Trust & Will, a remote-first digital estate planning leader, seeks a Controller to lead accounting across the company and subsidiaries. The role focuses on month-end close, tax compliance, and efficient AP/AR, while building scalable controls and automating processes with AI.

The ideal candidate has 10+ years of accounting experience, 4–5 in a leadership role, and a background in fast-scaling environments. CPA preferred; remote work option with competitive compensation.