Remote AI-Driven Controller: Automate Close & Elevate Finance

Trailhead Media LLC; Laurel (MS); Remote; USD 155,000 - 185,000; Full time

Benefits offered by this job

Medical benefits

Dental benefits

Vision benefits

HSA contribution

401k

Paid time off

Fully remote

Job summary

Trailhead Media LLC is seeking a Controller to own the accounting function end-to-end in a remote U.S. role with HQ in Laurel, MS. You will drive automation of the close, implement AI-driven workflows, and elevate the team’s AI fluency across finance processes.

You bring 7+ years of accounting, US GAAP expertise, and a track record of automating manual tasks using modern tools. Reports to CFO; fully remote with leadership access.

Qualifications

• 7+ years of progressive accounting experience.
• Strong technical accounting (US GAAP; ASC 606 a plus).
• Automation-first mindset with AI/tools experience.
• Ability to mentor and coach a remote team.
• Experience with debt covenant / lender reporting.
• Media/advertising or asset-intensive background preferred.

Responsibilities

• Own the full monthly close, financial statements, and the general ledger.
• Prepare covenant reporting for our senior credit facility and coordinate with auditors.
• Take manual processes and turn them into automated routines using AI.
• Build and extend the AI-driven finance stack for close, reconciliations and reporting.
• Coach the finance team on AI-first workflows and document playbooks.
• Own forecast and budget-to-actual variance analysis and business partnership.
• Serve as finance system owner across Sage Intacct, Datarails and Apparatix.

Skills

Automation

US GAAP

Debt covenants

Financial close

Leadership

Remote work

Tools

Sage Intacct

Datarails

Apparatix

Claude AI

Python

SQL

Job description

Trailhead Media LLC is seeking a Controller to own the accounting function end-to-end in a remote U.S. role with HQ in Laurel, MS. You will drive automation of the close, implement AI-driven workflows, and elevate the team’s AI fluency across finance processes.

You bring 7+ years of accounting, US GAAP expertise, and a track record of automating manual tasks using modern tools. Reports to CFO; fully remote with leadership access.