Assistant Controller

Who we’re looking for:

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.

What You'll Do:

• Master the Close & Revenue: Own the month-end close and lead revenue accounting (ASC 606) for our SaaS streams. Ensure everything is auditable and accurate.
• Optimize Order-to-Cash (O2C): Drive the full cycle from billing to collections. Partner with Sales and RevOps to eliminate process bottlenecks.
• System Evolution: Evaluate our current tech stack, identify gaps, and lead migrations to tools that are scalable and automated.
• AI Integration: Experiment with and implement AI tools to streamline reconciliations, flux analysis, and documentation with proper guardrails.
• Leadership & Partnership: Mentor junior staff and act as a bridge between Accounting and FP&A to turn financial data into actionable business insights.
• Audit & Controls: Strengthen internal controls and lead a "no-surprises" external audit process.

Our ideal candidate will have the following:

• The Foundation: 8+ years of progressive experience, starting with Big 4 audit. CPA required.
• SaaS Expert: Deeply fluent in ASC 606 and the nuances of recurring revenue models.
• Systems Architect: You’ve lived through ERP/Billing migrations and know what a "clean" data environment looks like.
• AI Enthusiast: You are energized by the potential of AI in finance and want to lead its thoughtful adoption.
• Hands-on Mentor: You’re happy to reconcile an account yourself if it means teaching a junior team member the "why" behind the work.
• Detail-Obsessed: You don’t stop until the numbers tick and tie.

The perks of working for us are great! 

You’ll get your foot in the door as our company continues to grow. We’re big believers in work-life balance and provide:

• Employer-paid health insurance (including dependent coverage)
• An employer-matched 401K retirement savings program from day 1 
• Paid Parental Leave
• Stock options
• Health + wellness reimbursements
• PTO that increases each year
• 15 paid holidays, including your birthday! 

As a fully remote team, we’ll make sure you have all the tools and equipment you need to make your home office a place where you can thrive. 

We're an equal opportunity employer. All applicants will be considered for employment without attention to age, race, color, religion, sex, sexual orientation, gender identity, national origin, veteran or disability status. We are committed to maintaining a drug-free workplace in compliance with applicable state laws.

The salary range for this role will be $180,000 - $200,000, DOE.