Controller - AI-Driven, Remote, Equity Eligible

Trust & Will; Philadelphia (Philadelphia County); Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Salary + Equity

Remote-first company culture

Excellent health benefits and 401(k)

Job summary

Trust & Will is seeking a Controller to lead accounting operations across our fast-growing platform. You will own the month-end close, tax compliance, and AR/AP while building scalable controls and a high-performing team. Collaboration with FP&A and CFO on strategy will be key.

Ideal candidates bring 10+ years in accounting with leadership, experience at a Big 4 or startup, and a track record applying automation to workflows. This remote-first role supports flexible work in a national scope.

Qualifications

• Minimum 10 years of accounting experience, with 4–5 years in a Controller/senior leadership role.
• CPA certification preferred.
• Experience applying AI/automation to accounting workflows.
• Experience designing internal controls for automated processes.
• Proficiency with Ramp, Rillet, Google Sheets and Excel.
• Knowledge of startups/IPO prep and regulatory reporting.

Responsibilities

• Own accounting operations for Trust & Will and subsidiaries; manage month-end close, tax compliance, AP/AR, and data integrity.
• Develop and maintain internal controls for scalability and risk management.
• Lead audits and reconciliations with accuracy down to the last detail.
• Manage accounting technology stack; collaborate with FP&A for integrated systems.
• Partner with CFO on financial strategy and cost analysis; drive optimization.
• Oversee vendor relationships and ensure policy compliance.

Skills

Accounting leadership

AI/Automation in accounting

Communication

Strategic mindset

Adaptability

Big 4/Startup experience

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will is seeking a Controller to lead accounting operations across our fast-growing platform. You will own the month-end close, tax compliance, and AR/AP while building scalable controls and a high-performing team. Collaboration with FP&A and CFO on strategy will be key.

Ideal candidates bring 10+ years in accounting with leadership, experience at a Big 4 or startup, and a track record applying automation to workflows. This remote-first role supports flexible work in a national scope.