Controller (AI-Forward) — Remote

Company: Trailhead Media

Location: Remote (U.S.) · HQ in Laurel, MS

Reports to: Chief Financial Officer (CFO)

Compensation: $155,000–$185,000 base + annual bonus (10–20%)

Employment type: Full-time

About Trailhead Media

Trailhead Media is a growing out-of-home advertising company. We own and operate advertising structures across multiple markets and run a real, complex finance function — a senior credit facility with covenant reporting, ASC 606 revenue recognition, asset retirement obligations, and a monthly close driven by workpapers, not guesswork.

What makes us unusual: we’ve already built an AI-first finance operation. Our close, forecasting, revenue reconciliation, commission reporting, and covenant compliance run on custom automation (Sage Intacct, Datarails, Apparatix, and a library of AI-driven routines built on Claude). We’re not “exploring AI” — we’re running on it, and we’re looking for a Controller who can own that system, push it further, and bring the rest of the team along with them.

The Opportunity

This is a do-the-work, build-the-machine seat — not a review-and-approve one. You’ll own the accounting function end to end, rebuild and automate it as you go, and help raise the whole team’s AI fluency so the way we work spreads beyond any one person. If you’re an experienced controller who is genuinely energized by replacing manual close steps with automation — and by teaching others to do the same — this role is built for you.

You’ll have unusual leverage: a finance environment already wired for automation, direct access to leadership, and a mandate to modernize rather than maintain.

What You’ll Own

Controllership & the close

• Own the full monthly close, financial statements, and the general ledger

• Management reporting and the supporting schedules behind every P&L and balance-sheet line

• Revenue recognition (ASC 606), prepaids, accruals, fixed assets & depreciation, ARO accretion, and lease accounting

• AP/AR oversight, cash, and account reconciliations

Debt covenant & external reporting

• Prepare covenant compliance reporting for our senior credit facility (leverage ratio, Adjusted EBITDA, quarterly deliverables)

• Support the annual audit and coordinate with external accountants and lenders

Rebuild & automate (the core of this role)

• Take manual, spreadsheet-bound processes and turn them into reliable, automated routines

• Own and extend our AI-driven finance stack — close automation, reconciliations, variance monitoring, and reporting

• Build controls and documentation so the automated function is auditable and durable, not fragile

Teach & elevate the team’s AI-first process

• Coach the finance team on our AI-first ways of working — turning one-off automations into shared, repeatable practice

• Translate AI and automation concepts for non-technical teammates so tools actually get adopted, not shelved

• Create the documentation, playbooks, and training that let the team run and extend the automated processes without you in the room

• Champion a culture of continuous improvement, where the team looks for the next thing to automate

FP&A & business partnership

• Own the forecast and budget-to-actual variance analysis

• Deliver the numbers leadership needs to make decisions, on time and without a fire drill

Systems

• Serve as the finance system owner across our ERP (Sage Intacct), Datarails, and Apparatix, and the automation layer connecting them

Who You Are

• 7+ years of progressive accounting experience, including running or effectively owning a month-end close

• Strong technical accounting (US GAAP; ASC 606 a plus)

• You automate. You’ve replaced manual work with tools, scripts, or AI — and you reach for automation by instinct, not as an afterthought. Comfort with AI tools (e.g., Claude), Python, SQL, or building workflows is a major plus

• You bring people with you. You can teach and mentor a team, explain AI and automation to non-technical colleagues, and turn what you build into something others can run

• Self-directed and execution-focused — you can own deliverables independently in a remote role

• Clear communicator who can explain the numbers to non-accountants

A CPA is not required. We care that you have the knowledge and experience to orchestrate this function and modernize it — not the letters after your name.

Bonus points

• Experience with debt covenant / lender reporting

• Media, advertising, real estate, or asset-intensive industry background

• Sage Intacct, Datarails, or Apparatix experience

• A track record of deploying AI or automation in a production finance setting — and of teaching others to use it

What We Offer

• Competitive cash compensation ($155K–$185K base) plus annual bonus

• Comprehensive medical, dental, and vision coverage

• Health Savings Account (HSA) with an employer contribution

• Company-paid telehealth

• 401(k) with a Safe Harbor employer match

• 4 weeks of paid time off, plus 14 paid company holidays

• Fully remote, with real ownership and direct access to leadership

Requirements

• 7+ years of progressive accounting experience, including running or effectively owning a month-end close

• Strong technical accounting (US GAAP; ASC 606 a plus)

• You automate. You’ve replaced manual work with tools, scripts, or AI — and you reach for automation by instinct, not as an afterthought. Comfort with AI tools (e.g., Claude), Python, SQL, or building workflows is a major plus

• You bring people with you. You can teach and mentor a team, explain AI and automation to non-technical colleagues, and turn what you build into something others can run

• Self-directed and execution-focused — you can own deliverables independently in a remote role

Clear communicator who can explain the numbers to non-accountants