Controller at Topstep in Chicago, IL

Summary
The Controller serves as the Company's senior accounting executive and strategic partner to the Chief Financial Officer, responsible for leading all accounting operations, financial reporting, internal controls, and regulatory compliance activities.
This role oversees the integrity of the Company's financial records and reporting processes while establishing scalable accounting infrastructure to support continued growth, operational excellence, and regulatory compliance. The Controller ensures the timely and accurate preparation of financial statements in accordance with U.S. GAAP, maintains a strong internal control environment, and leads audit and compliance readiness initiatives.
As a key member of the Finance leadership team, the Controller partners closely with executive leadership to support strategic decision-making, risk management, capital planning, and organizational growth. The successful candidate combines deep technical accounting expertise with strong business acumen, leadership capability, and the ability to influence cross-functional stakeholders.
Key Responsibilities
The essential duties and responsibilities include the following. Other duties may be assigned.
Leadership & Team Management
Lead and develop the accounting organization, including revenue, general ledger, and operational accounting functions.
Establish performance standards, close calendars, review cadences, and workflow prioritization.
Serve as the primary liaison between the finance and accounting function and external auditors, managing all audit deliverables, PBC schedules, and communications to ensure timely and efficient completion of annual and interim audits.
Own and manage accounting's relationships with key third-party platforms and service providers - including tax compliance tools, banking institutions, and financial system vendors - serving as the accountable point of contact for escalations, renewals, and cross-functional integration needs.
Provide coaching, technical guidance, and decision-making support across the accounting team.
Evaluate staffing needs and build a scalable team structure aligned with company growth.
Ensure accountability, consistency, and ownership across accounting deliverables.
Financial Reporting & Regulatory Compliance
Own the preparation and accuracy of monthly, quarterly, and annual financial statements.
Ensure financial statements are prepared in accordance with U.S. GAAP and applicable regulatory requirements, including trading and brokerage-related regulations (e.g., NFA or similar oversight bodies).
Maintain audit readiness across all financial reporting and supporting schedules.
Review and approve journal entries, reconciliations, and technical accounting memos.
Establish and maintain accounting policies for revenue, payouts, accruals, close, and internal controls.
General Ledger Oversight
Oversee balance sheet reconciliations, cash, prepaid expenses, accruals, fixed assets, leases, and clearing accounts.
Resolve complex reconciliation issues, aged items, and system-related discrepancies.
Own the month-end close calendar, review cadence, and quality standards.
Ensure all GL accounts are supported, documented, and maintained in an audit-ready state.
Maintain chart of accounts structure and alignment with reporting and FP&A.
Revenue & Payout Accounting Oversight
Oversee revenue recognition for subscriptions, resets, promotions, chargebacks, and refunds.
Ensure consistent application of ASC 606 performance obligations.
Manage deferred revenue logic, schedules, and release processes.
Oversee payout accounting and reconciliation across internal systems, processors, and bank data.
Ensure billing, payout, and accounting records align and accurately reflect economic activity.
Process Improvement & Internal Controls
Lead the design, implementation, and continuous improvement of the Company's internal control framework.
Identify financial reporting, operational, and compliance risks and implement mitigation strategies.
Ensure audit findings, control deficiencies, and process improvement opportunities are appropriately addressed.
Systems & Data Integrity
Own accounting system configuration, roles, workflows, approvals, and integrations.
Ensure clean data ingestion from upstream systems impacting billing, revenue, and payouts.
Partner cross-functionally to resolve data, system, or process gaps affecting accounting accuracy.
Cross-Functional Partnership
Partner cross-functionally with leadership and teams across the organization to support forecasting, operational decision-making, and reporting accuracy.
Present accounting findings, risks, and recommendations to senior leadership.
Ensure strong alignment between Accounting, FP&A, and Finance Operations.
Required Qualifications and Key Competencies
Bachelor's degree in Accounting, Finance, or related discipline.
CPA designation required or strongly preferred.
10 + years of progressive accounting and finance leadership experience.
5 + years managing accounting teams in a leadership capacity, including at least 2-3 years in a Controller role.
Extensive knowledge of U.S. GAAP, ASC 606, and financial reporting requirements.
Experience leading external audits and managing relationships with auditors, regulators, and financial institutions.
Demonstrated success building scalable accounting processes, controls, and teams in high-growth environments.
Strong executive presence with the ability to communicate effectively across all organizational levels.
Advanced ERP experience, preferably NetSuite or similar enterprise accounting platforms.
Preferred Qualifications
Experience in fintech, trading, payments, or subscription-based businesses.
Experience with multi-processor payout and clearing account reconciliation.
Background supporting regulatory, compliance, or broker-dealer environments.
Experience with AP automation tools and payroll platforms (eg. Paylocity).
Demonstrated success building scalable accounting teams and processes.
Company Culture & Perks
Topstep is an engaging working environment which ranges from fully remote to hybrid. We foster a culture of collaboration with cameras on during meetings and a robust Slack environment for communication.
Seven Company-paid Holidays and generous Family Leave. Paid time off is front-loaded.
Competitive 401(k) matching, health, dental, and vision insurance is offered for full time employees.
Vacations are encouraged with a bonus for taking 5 consecutive days. Employee referrals are bonused. Topstep offers a food and groceries budget and contributes towards health and wellness.
New Hire Base Salary Range
$235,000 - $275,000 annually.
Bonus: This position is eligible for a performance-based bonus as provided by the plan terms and governing documents.
The compensation offered will take into account the internal compensation structure and may vary depending on the candidate's geographic region, job-related knowledge, skills, and experience, among other factors.
Equal Opportunity Employer
Topstep is an Equal Opportunity Employer. We are committed to fostering an inclusive environment where all employees and applicants are valued. All qualified candidates will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, age, disability, or veteran status, in compliance with applicable federal, state, and local laws.
Interested in the role? Apply today with your resume and cover letter!
The collection, use, and handling of your data provided in response to this job posting is described further in our Privacy Policy. If you are a California resident, please review our California Notice at Collection.
Notice of Use of Artificial Intelligence in Recruitment and Hiring: Notice Pursuant to 775 ILCS 5/2-102(L). Topstep LLC uses artificial intelligence ("AI") in connection with its recruitment and hiring process. Examples include, but are not limited to, AI tools used to improve job descriptions, generate interview questions, draft communications, assist with scheduling, and source candidates, as well as AI features built into third-party platforms such as LinkedIn, Indeed, and Glassdoor. Topstep will not use AI that has the effect of subjecting employees or applicants to discrimination on the basis of any protected class under the Illinois Human Rights Act.