Controller

Topstep•Chicago, IL

18d•$235,000 - $275,000•Hybrid

About The Position

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.

Requirements

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.

Nice To Haves

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.

Responsibilities

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.
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.
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.
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.
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.
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.
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.