Controller (AI-Forward)

Job overview

The Controller (AI-Forward) role is remote in the United States; Trailhead Media is headquartered in Laurel, MS. Compensation is $155,000–$185,000 per year base, plus an annual bonus of 10%–20%. Trailhead Media operates out-of-home advertising structures across multiple markets. The Controller owns the accounting function and monthly close while improving and automating finance processes. The role also maintains reliable financial reporting and controls, supports forecasting and covenant reporting, and helps the finance team adopt repeatable AI-enabled workflows.

What you'll do

• Own the monthly close, financial statements, general ledger, management reporting, and supporting schedules
• oversee revenue recognition, AP/AR, cash, reconciliations, fixed assets, and lease accounting
• prepare debt covenant reporting and support audits
• automate manual finance processes and extend AI-driven tools
• document controls and workflows
• coach the finance team on AI-first practices
• own forecasts and variance analysis
• administer Sage Intacct, Datarails, Apparatix, and connected automation.

What we're looking for

Skills & competencies

controller

ai-forward finance

remote us

trailhead media

full-time

$155k–$185k base

annual bonus

accounting

monthly close

financial automation

ai workflows

debt covenant reporting

sage intacct

out-of-home advertising

Work arrangement

• Weekend coverage required

Benefits & perks

• Medical, dental, and vision coverage
• employer-contributed HSA
• company-paid telehealth
• 401(k) with Safe Harbor match
• four weeks of paid time off
• 14 paid company holidays.

Why this role

Fully remote U.S. role; CPA is not required. Requires 7+ years of progressive accounting experience, including ownership of a month-end close.

About the employer

Trailhead Media LLC is hiring for this role. Industry: Indoor and Outdoor Display Advertising. Sector: 54.