Assistant Controller

ParentSquare

9d•Remote

About The Position

ParentSquare is looking for a hands-on, AI-forward Assistant Controller to build a scalable finance function. Reporting to the VP of Accounting, you won’t just oversee the books—you’ll evolve our systems, integrate AI into our workflows, and mentor a growing team. We need a "fixer" who loves digging into the numbers to build a more efficient system. You’ll be joining a mission-driven team dedicated to improving student lives through better communication. If you're "scrappy," curious, and ready to build a modern finance org, let’s talk.

Requirements

8+ years of progressive experience, starting with Big 4 audit.
CPA required.
Deeply fluent in ASC 606 and the nuances of recurring revenue models.
Experience with ERP/Billing migrations.
Knowledge of what a "clean" data environment looks like.
Energized by the potential of AI in finance and desire to lead its thoughtful adoption.
Willingness to reconcile an account yourself to teach junior team members.
Detail-oriented; ensures numbers tick and tie.

Responsibilities

Own the month-end close and lead revenue accounting (ASC 606) for SaaS streams.
Ensure all accounting is auditable and accurate.
Drive the full cycle of Order-to-Cash (O2C) from billing to collections.
Partner with Sales and RevOps to eliminate process bottlenecks.
Evaluate the current tech stack, identify gaps, and lead migrations to scalable and automated tools.
Experiment with and implement AI tools to streamline reconciliations, flux analysis, and documentation with proper guardrails.
Mentor junior staff.
Act as a bridge between Accounting and FP&A to turn financial data into actionable business insights.
Strengthen internal controls.
Lead a "no-surprises" external audit process.