Controller (VP - Finance)

About Otter Learning

Founded in 2019, Otter Learning is a PE-backed early childhood education operator that has doubled its footprint roughly every two years. Today, Otter operates across eight states and continues to scale aggressively through both acquisitions and organic growth. We move fast, invest in infrastructure, and build the systems to support the next stage.

The Role

Otter is building a modern, data-driven finance function that pairs experienced operators with automation to deliver institutional-grade reporting, tight controls, and real-time visibility. The Controller will be central to that build. This is a high-visibility role with direct exposure to senior leadership, founders and PE sponsors, with a growth trajectory as the platform scales.

We’re looking for someone who is equal parts operator and builder. You’ll own the monthly close, manage the general ledger, and oversee financial reporting across a multi-entity portfolio, but you’ll also be expected to challenge legacy processes and automate everything that doesn’t require human judgment. This isn’t a sit-back-and-manage role. You’ll roll up your sleeves, get into the details, and build scalable systems that compound in value as Otter continues to grow.

You’ll report directly to the SVP of Finance and play a central role in the continued buildout of the finance function. The right candidate sees process automation not as a nice-to-have but as a core part of the controllership mandate.

What You’ll Own

Monthly Close \& Financial Reporting

• Lead the monthly, quarterly, and annual close process across all Otter entities

• Prepare consolidated financial statements, management reporting packages, and board-ready materials

• Own the general ledger, including chart of accounts maintenance, journal entry review, and inter-company eliminations

• Manage bank reconciliations, AP/AR reconciliations, and balance sheet account reconciliations

• Deliver variance analysis and commentary at both the school level and consolidated level

Process Automation \& Systems

• Identify, design, and implement automation for recurring accounting workflows - journal entries, reconciliations, report generation, invoice processing

• Partner with finance leadership and the data engineering function to connect financial systems into automated pipelines

• Evaluate and deploy tools that reduce manual effort: AI-assisted coding, rules-based posting, exception-based workflows

• Build and maintain documentation for all automated processes, ensuring auditability and knowledge continuity

• Champion a “automate first” mindset within the finance team—if a task is rules-based and repeatable, it should not be manual

Compliance, Audit \& Internal Controls

• Lead the annual audit end-to-end—manage the timeline, prepare and deliver PBC items, coordinate confirmations, and serve as the primary point of contact with external auditors

• Design, implement, and maintain internal controls across all entities to ensure compliance with GAAP, lender covenants, and PE sponsor reporting requirements

• Drive lender compliance reporting, including covenant calculations, certification packages, and ongoing lender communication

• Manage state subsidy reconciliations and ensure timely filings across all applicable programs

• Oversee payroll-related accounting, including reconciliation of payroll journal entries and benefits

Cash Management \& Treasury

• Monitor daily cash positions across multiple banking relationships using automated feeds

• Manage cash flow forecasting, payment scheduling, and vendor payment runs

• Support treasury operations including cash sweeps and concentration banking workflows

Who You Are

Required

• 10\+ years of progressive accounting experience, including 2\+ years in a controller or assistant controller role

• 4\+ years of experience in a Big 4 or national public accounting firm, or equivalent professional services environment

• Demonstrated track record of building or improving accounting process automation - not just using tools, but designing workflows that eliminate manual work

• Multi-entity consolidation experience

• Strong technical GAAP knowledge, particularly around revenue recognition, lease accounting, and multi-entity consolidation

• Hands-on, roll-up-your-sleeves operator who is equally comfortable reviewing journal entries and presenting to the board

• CPA required

Highly Preferred

• Experience at a PE-backed, multi-unit services business (healthcare, dental, veterinary, fitness, education, or similar roll-up models)

• Sage Intacct power user: deep knowledge of dimensions, multi-entity setup, consolidation, and reporting

• Experience with Ramp (expense management, virtual cards, GL auto-tagging)

• Familiarity with data and efficiency tools (VBA, PowerQuery, Power BI) or strong willingness to learn and partner with a data-forward finance team

The Intangibles

• You see a broken process and your instinct is to fix it, not work around it

• You’re energized by building from scratch, not maintaining the status quo

• You communicate clearly with non-finance operators (school directors, regional managers) and can translate financial data into operational action

• You thrive in a lean team environment where ownership is high and bureaucracy is low

• You’re curious about AI and automation and excited to work in a finance function that is actively evolving with AI

Compensation \& Benefits

• Competitive base salary commensurate with experience

• Annual performance bonus

• Eligible for equity participation

• Health, dental, and vision insurance

• 401(k) with company match

• Unlimited PTO and paid holidays