Assistant Flight Operations Controller Jobs in Chicago, IL

Summary

The Assistant Controller serves as a key leader within the accounting organization and acts as a direct partner to the Controller, translating accounting policy into day-to-day processes. 

This role owns the day-to-day integrity of the general ledger, the accuracy and supportability of revenue accounting, the month-end close process and calendar, and the accuracy of balance sheet and income statement accounts across all entities. The Assistant Controller leads and develops the GL and revenue accounting team to ensure the accounting records are complete, supported, and audit-ready.    

As a key member of the Finance team, the Assistant Controller partners cross functionally with other departments (including but not limited to Treasury, HR, and Product/Engineering) and outside advisors to support the Company's continued growth and operational scalability and ensure accurate financial reporting.  The successful candidate combines strong technical accounting expertise with hands-on leadership, the ability to bring order to high-volume and high-complexity data environments, and the judgment to escalate the right issues to the Controller and CFO. 

Key Responsibilities 

The essential duties and responsibilities include the following. Other duties may be assigned. 

Leadership & Team Management

• Directly manage and develop the accounting team, including workload prioritization and review across both functions.
• Set daily and monthly priorities for the team in line with the month-end close calendar established with the Controller.
• Provide technical accounting guidance, coaching, and day-to-day decision-making support.
• Identify staffing, training, and process gaps and determine recommended solutions to provide to the Controller.
• Hold the team accountable for timely, accurate, and well-documented deliverables.

General Ledger & Month-End Close

• Own execution of the month-end close calendar, including bank transaction uploads, payroll expenses, expense report coding, fixed asset and intangible asset amortization, prepaids and accruals, balance sheet reconciliations, and journal entry review.
• Ensure every GL account has a clearly identified owner, a documented process, and supporting schedules sufficient for audit.
• Oversee balance sheet reconciliations across cash, prepaids, accrued expenses, fixed assets, intangible assets, intercompany/clearing accounts, etc.
• Resolve aged and complex reconciling items, including system-driven discrepancies between NetSuite, payment processors, the trading platform, and bank data.
• Maintain and continuously improve the chart of accounts and account mapping in partnership with the Controller and FP&A.

Revenue & Payout Accounting 

• Oversee revenue recognition for subscriptions, resets, promotions, chargebacks, and refunds.
• Ensure consistent application of ASC 606.
• Manage deferred revenue schedules, rollforwards, and monthly release entries. Ensure supporting data (trading platform, payment processor, Sigma/Snowflake extracts) is reconciled before posting.
• Oversee the 3-way reconciliation process between payment processors, the general ledger, and bank data, and ensure discrepancies are researched and resolved timely.
• Oversee payout accounting and reconciliation across internal systems, processors, and bank data. Ensure payout returns are properly tracked and accounted for. 
• Ensure billing, payout, and accounting records align and accurately reflect activity across both revenue and payout processes. 

Financial Reporting Support & Regulatory Compliance

• Support the Controller in preparing accurate monthly, quarterly, and annual financial statements by ensuring underlying GL and revenue schedules are complete, reconciled, and ready ahead of reporting deadlines.
• Review journal entries, reconciliations, and account roll-forwards prepared by the team for accuracy and adequate support prior to Controller review.
• Flag account-level risks, unusual fluctuations, or open items to the Controller in time for resolution before financial statements are finalized.
• Assist in preparing supporting schedules and analysis requested by the Controller, CFO, or external auditors for financial reporting purposes.
• Partner with the Controller to establish and maintain accounting policies for revenue, payouts, accruals, close, and internal controls.

Process Improvement & Internal Controls

• Partner with the Controller on the design, implementation, and continuous improvement of the Company's internal control framework.
• Identify control gaps and reconciliation breakdowns across cash, payouts, and revenue processes. Design and implement corrective processes and mitigation strategies. 
• Partner with the Controller to ensure audit findings, control deficiencies, and process improvement opportunities are appropriately addressed.
• Own accounting policies & procedures, including SOPs, ensuring the team maintains and updates the policies on a timely basis.  

Systems & Data Integrity

• 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.
• Own and lead system implementations and improvements to accounting systems. 
• Partner cross-functionally to ensure adoption of new systems, product launches, etc. are properly accounted for.
• Drive adoption of tools (e.g., reconciliation/automation tools) to reduce manual, spreadsheet-based processes.

Cross-Functional Partnership

• Present accounting findings, risks, and recommendations to the Controller and CFO.
• Act as a thought partner to the Controller on technical accounting questions, close timing, and account treatment.
• Partner internally with Treasury, FP&A, HR, Product, Engineering, and outside advisors (audit, tax, accounting advisors, ERP advisors, etc.) to ensure consistent, well-supported accounting.
• Communicate risks, open items, and recommendations clearly to the Controller and other Finance leadership.

Required Qualifications and Key Competencies

• Bachelor's degree in Accounting, Finance, or related discipline.
• CPA designation required or strongly preferred.
• 7 + years of progressive accounting and finance leadership experience.
• 2 + years managing accounting teams in a leadership capacity.
• Strong working knowledge of U.S. GAAP, ASC 606, and financial reporting requirements.
• Experience assisting with external audits and managing relationships with auditors, regulators, and financial institutions.
• Demonstrated ability to bring structure and process-discipline to high-volume, data-intensive reconciliation environments.
• Strong ERP experience, preferably NetSuite or a similar enterprise accounting platform.
• Excellent written and verbal communication skills, with the ability to explain technical accounting matters clearly to non-accounting stakeholders.
• Strong executive presence with the ability to communicate effectively.

Preferred Qualifications

• Experience in fintech, trading, payments, or subscription-based businesses.
• Experience with high-volume transactions and multi-processor payout and clearing account reconciliations.
• Demonstrated success managing scalable accounting teams and processes.
• Experience with reconciliation automation tools.
• Experience supporting external audits and working with outside accounting/tax advisors.

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

• $170,000 - $200,000 annually.
• 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.
• This position is eligible for a performance-based bonus as provided by the plan terms and governing documents.

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!

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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.

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.