Chief Accountant, Trilogy (Remote) - $100,000/year USD

Most Chief Accountants gradually stop doing accounting. Their calendars fill with status meetings, task chasing, and people administration while their technical skills go stale. This role takes the opposite path.

You will run global finance operations through a team of Senior Accountants while staying close enough to the work to know whether it is actually right. You'll inspect invoices, payments, reconciliations, allocations, and other finance outputs; diagnose the accounting or process failures behind errors; and turn those findings into written coaching that prevents the same mistakes from happening again. When a critical deadline or difficult finance problem demands it, you will still be capable of getting hands-on yourself.

Trilogy's Central Finance team operates differently from a traditional accounting organization. We automate routine coordination and continuously look for ways AI and automation can eliminate manual work, leaving finance professionals focused on judgment, quality, and improvement. You'll get exposure to complex global finance operations while retaining the technical edge that many managers lose as they advance. If you want management responsibility without becoming a professional meeting-attendee, this is where your accounting expertise becomes leverage.

What You Will Be Doing

• Run day-to-day finance operations through Senior Accountants, continuously prioritizing work based on deadlines, business impact, dependencies, and financial risk.
• Inspect finance dashboards and completed work to ensure bills, invoices, payments, bank transactions, reconciliations, control accounts, revenue, and spend allocations are accurate and current.
• Diagnose quality failures using your own accounting expertise, identifying whether the root cause is incorrect data, system configuration, accounting treatment, or process execution.
• Write evidence-based coaching that explains what went wrong, how to correct it, and how to prevent it from happening again.
• Identify opportunities to use AI, LLMs, and automation to eliminate manual work and improve the speed and accuracy of finance operations.
  
  

What You Won’t Be Doing

• Spending your week chasing status updates, assigning routine tasks, or sitting in project-management meetings.
• Personally processing every transaction because delegating is easier than developing a strong accounting team.
• Giving generic performance feedback disconnected from actual invoices, payments, reconciliations, reports, or other finance outputs.
• Accepting recurring errors and inefficient manual processes as “just how finance works.”
  
  

Chief Accountant Key Responsibilities

Build a high-performing finance operations team that consistently produces accurate, timely finance deliverables while continuously improving quality and reducing unnecessary manual work.

Basic Requirements

• A degree in Accounting or Finance.
• A recognized professional accounting qualification such as CPA, ACA, ACCA, CIMA, or equivalent.
• Experience on at least five audits involving a Big 4 accounting firm, either as the auditor or the client.
• Accounting or finance experience within an organization with at least $100M USD in revenue.
• People-management experience with direct responsibility for finance or accounting professionals.
• Hands-on experience across AP, AR/customer invoicing, bank and control-account reconciliations, and revenue and spend allocation.
• Experience prioritizing and allocating operational finance work across a team while managing deadlines and resolving blockers.
• Experience embedding AI or LLM tools into a recurring, high-volume finance transaction-processing workflow, beyond ad hoc prompting or reporting-only analysis, with a clear impact on efficiency or accuracy.
• Ability to work US business hours.
  
  

Nice-to-have Requirements

• Experience designing or building finance workflow automations using tools such as n8n, Lovable, Claude Code, or similar platforms.
• Experience managing finance operations across multiple business lines or international entities.
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, innovating new technology, and incubating new businesses.

Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack.

Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career in leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $50 USD/hour, which equates to $100,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-3147-PK-FederalC-ChiefAccountan