AI-Driven Controller for Rapid-Growth FinOps (Remote)

Trust & Will; Florida; Remote; USD 165,000 - 185,000; Full time

Benefits offered by this job

Health benefits including medical, 
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100% premiums covered for employees &/

401(k) with up to 4% company match

Flexible work schedule

Generous PTO and holidays

Learning & development reimbursement

Work-from-home stipend

Job summary

Trust & Will is seeking a Controller to lead accounting and financial operations during a growth phase. You will own month-end close, tax compliance, and AP/AR while advancing internal controls and automation. The role collaborates with FP&A and reports to the CFO.

We value AI-native operators who can design repeatable workflows, mentor staff, and communicate complex financials to non-finance stakeholders. This remote-friendly role requires leadership in a fast-paced startup environment.

Qualifications

• 10+ years of accounting experience with 4–5 years in a Controller or leadership role.
• CPA certification preferred; strong financial reporting and controls.
• Hands-on AI/automation experience in accounting workflows.
• Internal controls for automated/AI-assisted processes.
• Proficiency in Ramp, Rillet, Google Sheets and Excel.
• Experience with startup/IPO-relevant regulations and reporting.

Responsibilities

• Own accounting for Trust & Will and subsidiaries; close monthly books.
• Develop and maintain internal controls to scale operations.
• Lead audits and ensure accuracy in accounts.
• Manage accounting tech stack; collaborate with FP&A.
• Partner with CFO on cost analysis and financial planning.
• Oversee vendor relationships and policy compliance.

Skills

Dynamic experience

AI automation

Effective communicator

Analytical thinker

Adaptability

Education

CPA certification preferred

Tools

Ramp

Rillet

Google Sheets

Excel

Job description

Trust & Will is seeking a Controller to lead accounting and financial operations during a growth phase. You will own month-end close, tax compliance, and AP/AR while advancing internal controls and automation. The role collaborates with FP&A and reports to the CFO.

We value AI-native operators who can design repeatable workflows, mentor staff, and communicate complex financials to non-finance stakeholders. This remote-friendly role requires leadership in a fast-paced startup environment.