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Jr. Controller (Head of Finance Track)

Classkick
Chicago, IL Full Time
POSTED ON 1/9/2026
AVAILABLE BEFORE 7/5/2026

Classkick is a profitable, YC-backed collaborative learning platform used by 10M students and teachers across 100 countries. Our product consistently ranks in the 95th percentile for session time, powering over 100 million minutes of learning each month across lessons, practice, assessments, and homework.

Teachers choose Classkick because students engage more deeply and succeed through timely, personalized feedback.The Opportunity


This is Classkick’s first internal finance hire and a foundational role in the company. You will own day-to-day accounting and operational finance while helping build the systems, processes, and financial discipline needed to support a growing SaaS business.


Over time, this role will expand into FP&A, forecasting, SaaS metrics, financial modeling, and process automation, with a clear path to Head of Finance. You’ll work closely with the CEO and leadership team and have broad ownership from day one.What You Will Own


Financial Operations & Accuracy

  • Own monthly close, revenue recognition, reconciliations, and overall financial integrity
  • Maintain and improve the Annual Operating Plan (AOP)
  • Prepare monthly financial summaries and insights for leadership


Cash & Collections

  • Improve accounts receivable performance and cash predictability
  • Manage billing, invoicing, and collections end to end


Cross-Functional Collaboration

  • Partner with Success, BizOps, and Support to ensure accurate data and clean financial workflows
  • Build clarity, transparency, and trust across the organization


Systems & Process Improvement

  • Streamline, automate, and document financial processes
  • Improve reporting speed and quality through better tools and workflows


Traits We’re Looking For

  • Curious and eager to understand the business deeply
  • Ambitious and excited to grow into a Head of Finance role
  • Detail-oriented with strong follow-through
  • Self-starter who creates structure where needed
  • Clear, proactive communicator
  • Systems-minded and motivated by process improvement


Backgrounds That Fit (Any of These)

  • Big 4 audit or advisory (Senior Associate level)
  • Investment banking, FP&A, or transaction services
  • Startup finance or BizOps with strong accounting exposure


Compensation

  • Year 1: $95,000 base 10% bonus
  • Growth Path: 25%–45% total compensation growth over 2–3 years based on performance

Salary : $95,000

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