Job Description: Controller

Company Overview

At HopSkipDrive, our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around the country.

Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than five million rides across over 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Position Overview

HopSkipDrive is seeking a strategic and hands-on Controller to lead the Accounting team. This role is crucial for ensuring the integrity of our financial reporting, supporting compliance, and building scalable systems and processes as the business grows. The ideal candidate is passionate about building scalable processes and teams in a fast-paced, high-growth environment, confident in navigating complexity, grounded in GAAP expertise, and energized by the opportunity to lead through growth and drive operational excellence.

Responsibilities

• Financial Reporting: Lead the preparation of accurate, timely financial statements to inform strategic business decisions.
• Month-End Close: Own and continuously improve the month-end close process to increase rigor, speed, and accuracy.
• Accounting Policies: Develop and enforce accounting policies and procedures in alignment with GAAP best practices.
• Operations Optimization: Optimize accounting operations including accounts receivable and accounts payable.
• Cross-Functional Partnership: Partner cross-functionally to analyze financial performance and support business growth initiatives.
• Internal Controls & Audit: Enhance and monitor internal controls, financial systems, and audit readiness to ensure compliance.
• ERP System: Oversee the optimization of the ERP system to support scalable operations.
• External Audits: Serve as the primary liaison for external auditors and manage all aspects of the annual audit process.
• Team Leadership: Manage, mentor, and develop the accounting team for scale.

Requirements

• Education & Certification: CPA designation and a Bachelor’s or Master’s degree in Accounting.
• Experience:
  • 15+ years of progressive accounting experience.
  • 4+ years in a Controller-level role.
  • Proven experience leading month-end close and preparing GAAP-compliant financial statements.
  • Demonstrated success in optimizing accounting systems, including ERP platforms.
  • Strong leadership experience with a track record of building and developing high-performing teams.
  • Experience managing audits and serving as the primary contact for external auditors.
• Skills:
  • Deep understanding of U.S. GAAP and internal controls.
  • Effective cross-functional collaborator with strong communication skills across technical and non-technical audiences.

Our Investment In You

• Equity: Every full-time employee receives equity.
• Benefits: Flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA.
• Opportunity: Work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential.
• Compensation:
  • Base Salary Range: $200,000 - $240,000.
  • This position is remote, and compensation will be aligned with the location where the position is filled.
  • Final compensation will be determined by factors such as relevant work experience, skill set, certifications, and specific work location.
  • Total compensation package includes equity stock options and a target bonus.
• Workplace: HopSkipDrive proudly operates as a drug-free workplace and is committed to fair and equitable compensation practices.

Equal Opportunity Employer

HopSkipDrive is proud to be an equal opportunity employer.