Controller

Insider, Inc.; New York (NY); On-site; USD 180,000 - 220,000; Full time

Benefits offered by this job

Meaningful Equity Stake

Subsidized Medical, Dental, Vision insurance

401(k)

Open vacation policy

Work-from-anywhere days

Job summary

Stepful in New York, NY is seeking a Controller to establish world-class accounting operations. This hybrid role will involve overseeing all accounting functions, preparing financial statements, and leading audits with Big 4 firms. Key qualifications include a CPA, 8-12 years of accounting experience, and strong leadership skills. The position offers a target salary range of $180,000 - $220,000 and a range of benefits, including equity and flexible vacation policies.

Qualifications

• 8–12+ years of progressive accounting experience with 5 years in leadership.
• Track record of hiring and developing high performing teams.
• Experience with Big 4 audits.

Responsibilities

• Own all aspects of accounting operations including GL, AP, AR.
• Prepare financial statements in accordance with US GAAP.
• Lead preparation for external audits with Big 4.

Skills

CPA

Leadership experience

Public accounting background

Operational accounting skills

Strong ERP experience

Education

Bachelor's degree in Accounting or Finance

Tools

Rillet

Job description

About Stepful

Stepful is reimagining allied healthcare training by offering affordable, online, instructor‑led, and AI‑supported programs that help learners—regardless of background or circumstance—launch high‑demand healthcare careers.

In addition to our direct‑to‑consumer training, Stepful partners with leading healthcare institutions to address the growing national shortage of healthcare workers. Our graduates, including Medical Assistants, Pharmacy Technicians, Nurses, and more, form the talent pipelines at major employers like CVS, NY‑Presbyterian, HCA, Providence, and Walgreens.

Stepful is backed by Y Combinator, Reach Capital, and AlleyCorp, with a recent $31.5M Series B led by Oak HC/FT. We were named the #1 EdTech company in the U.S. by TIME for 2025.

We’re improving access to quality healthcare for everyone, everywhere, and improving access to healthcare careers for those who need them most.

Our values

• Care first: We do whatever it takes for our students to succeed.
• Learn quickly: We test, learn with data, and iterate.
• Build together: We win when we rely on each other.
• Own it: We show up, take initiative, and show pride.

The opportunity

We’re adding a Controller to our Finance team to establish world‑class accounting operations and lead our transition to Big 4 audits. You’ll play a critical role in building scalable processes, ensuring audit readiness, and supporting our leadership team with strategic financial insights as we prepare for our next phase of growth.

This role reports directly to the Head of Finance and partners closely with cross‑functional teams across the organization. You will establish robust accounting operations while maintaining the rigor required for financial accuracy and audit compliance.

This is a hybrid opportunity requiring three days/week (Tuesday, Wednesday, Thursday) working out of our office located in TriBeCa.

What you’ll do

• Own all aspects of accounting operations, including GL, AP, AR, payroll, revenue recognition, and tax compliance
• Prepare and review monthly, quarterly, and annual financial statements in accordance with US GAAP
• Lead preparation for and management of annual external audits with Big 4 accounting firm
• Oversee revenue recognition policies in accordance with ASC 606, ensuring accuracy for B2C and B2B subscription usage models
• Manage GL reconciliations and maintain internal controls to ensure financial integrity
• Maintain compliance with federal, state, and local reporting requirements, including timely and accurate preparation of tax filings
• Implement and monitor internal controls to ensure compliance with audit requirements
• Optimize accounting workflows and documentation for scalability
• Partner with FP&A on budgeting, forecasting, and financial analysis
• Manage relationships with auditors, tax advisors, and other external partners
• Oversee an in‑house and outsourced team of accounting professionals, including overseeing accounting operations for a recent acquisition
• Lead ongoing accounting ERP implementation with Rillet
• Drive process improvements to enhance accuracy, efficiency, and transparency

What you’ll bring

• CPA with 8–12+ years of progressive accounting experience, including at least 5 years in a leadership role
• Track record of hiring, training, and developing high performing teams
• Public accounting background (Big 4 preferred) with direct audit experience
• Experience in high‑growth venture‑backed companies (ideally Series B–D stage)
• In‑depth knowledge of US GAAP, ASC 606, and internal control frameworks
• Proven track record of successfully preparing a company for Big 4 audits
• Hands‑on operational accounting skills with ability to dive into details while managing strategic initiatives
• Strong ERP experience (Rillet is a plus) and ability to lead system implementations
• Exceptional organizational skills with ability to manage multiple priorities under tight deadlines

Bonus points if

• Experience in SaaS, technology‑enabled services, or subscription‑based revenue model
• Exposure to IPO readiness
• Advanced Excel and experience with business intelligence tools

Interview Process

• Intro call with Talent Acquisition team
• Interview with Hiring Manager
• Take‑Home Assignment
• On‑site Panel Interview

Benefits and Compensation

• Meaningful Equity Stake
• Subsidized Medical, Dental, and Vision insurance plan options
• 401(k)
• FSA, HSA and commuter benefits
• Open vacation policy, including:
  • Guidance of 15 days PTO annually
  • 15 work‑from‑anywhere days
  • 10 public holidays observed for 2026

The target base salary range for this opportunity is $180,000 - $220,000 and is part of a competitive total rewards package including equity and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, internal pay equity and other relevant business considerations.

Stepful is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic.