Head of Finance in Chicago, Illinois at Aeropay

Head of Finance
Reports to: CEOFLSA Status: Exempt
About Us:
We have been recognized as one of Built In Chicago’s Best Startups to Work for in 2026!
Aeropay is a financial technology company modernizing money movement with pay by bank solutions. Headquartered in Chicago and backed by leading investors, Aeropay enables businesses to accept compliant, cashless payments through direct bank-to-bank (ACH) transfers, eliminating card fees and outdated payment rails. Powering online checkouts, in-store transactions and embedded payments, Aeropay’s flexible APIs and integrations are built on a secure and scalable infrastructure with compliance at the core. In industries where risk mitigation and user experience matter most, our platform gives our partners a faster, safer and more intuitive way to pay.
Aeropay is redefining what it means to pay—and get paid—by bank.
Position Overview:
The Head of Finance will serve as a key strategic partner to Aeropay’s executive leadership team, responsible for leading the company’s financial planning, forecasting, reporting, treasury operations and overall financial strategy during its next phase of growth.
This role will oversee the day-to-day workflows of the Finance department while helping to build the financial infrastructure, reporting frameworks and operational rigor required to support a rapidly scaling fintech organization. The ideal candidate combines strong financial acumen with a hands-on approach and is comfortable rolling up their sleeves to solve complex problems while simultaneously operating as a strategic advisor to executive leadership.
In addition to leading core finance operations, this individual will play a highly visible role in preparing financial analyses, executive reporting and board-level materials. We are seeking a finance leader who can transform complex financial information into clear, compelling narratives that support strategic decision-making and effectively communicate company performance, opportunities and risks to executive leadership, investors and board members alike.
Key Responsibilities:
Financial Planning & Strategy:

• Partner with executive leadership to develop and execute Aeropay’s long-term financial strategy
• Lead company-wide budgeting, forecasting and financial planning processes
• Develop financial models and scenario analyses to support strategic decision-making
• Provide actionable insights and recommendations that support company growth and operational efficiency
• Establish and monitor financial KPIs and operational performance metrics

Board Reporting & Executive Finance:

• Partner closely with the CEO, COO and executive leadership team on company-wide financial planning and strategy
• Lead the preparation of board presentations, investor materials and executive-level reporting packages
• Develop clear and compelling financial narratives that communicate company performance, opportunities and risks
• Present financial analyses and recommendations to executive leadership and board stakeholders
• Support fundraising activities, financial diligence efforts and investor-related initiatives as needed
• Continuously evolve reporting frameworks to support a growing and increasingly complex business

Financial Operations & Treasury:

• Oversee cash management, liquidity planning and treasury operations
• Monitor financial performance and identify opportunities to improve operational efficiency and profitability
• Partner with Accounting to ensure accurate financial reporting and compliance with applicable standards
• Develop scalable processes and controls that support business growth and operational excellence
• Support financial infrastructure and systems improvements across the organization
• Assume a leadership role in negotiating key vendor pricing and contracts, securing best-case financial outcomes for Aeropay while partnering effectively with cross-functional stakeholders

Cross-Functional Leadership:

• Serve as a strategic finance partner to leaders across Product, Business Operations, Revenue, Risk & Compliance and Engineering
• Collaborate on company-wide initiatives that impact financial performance and long-term planning
• Support pricing strategy, resource allocation decisions and business case development
• Help drive accountability and performance management through data-driven decision-making

Team Leadership:

• Lead, mentor, grow and develop Aeropay’s Finance and Accounting team
• Foster a culture of accountability, collaboration and continuous improvement
• Establish departmental OKRs, development plans and performance expectations
• Support organizational scaling efforts as the company continues to grow

Qualifications:

• Bachelor’s degree in Finance, Accounting, Economics, Business Administration or a related field
• MBA, CPA or other advanced financial certification preferred
• 15-20 years of progressive experience in finance, FP&A, treasury, accounting or related financial leadership functions
• Experience serving as a senior finance leader within fintech, payments, marketplace, SaaS or other transaction-intensive business environments
• Strong foundation in corporate accounting, treasury management and financial planning & analysis
• Demonstrated experience building and scaling financial operations within high-growth organizations
• Proven experience preparing, presenting and defending board-level reporting and executive financial materials
• Strong financial storytelling skills with the ability to translate complex financial information into actionable business insights
• Experience supporting fundraising, investor diligence and strategic financing initiatives
• Strong understanding of forecasting, liquidity management, cash planning and financial reporting
• Exceptional analytical, organizational and problem-solving abilities
• Excellent communication and executive stakeholder management skills
• Ability to operate both strategically and tactically in a fast-paced, evolving environment

Working Location, Compensation & Benefits:

• This role is expected to be in office at Aeropay’s downtown Chicago HQ weekly from Monday through Thursday
• Salary Range: $250K - $275K base salary (DOE)
• Benefits Offered:
  • Comprehensive Medical, Dental & Vision Coverage
  • Maternity/Paternity Leave
  • 401(k) Employer Match
  • Flexible PTO

NOTE: This job description is not intended to be all-inclusive. Employees may perform other related duties as negotiated to meet the ongoing needs of the organization.
Aeropay is an equal opportunity employer and is committed to providing a workplace free from harassment and discrimination. We celebrate the unique differences of our employees because that is what drives curiosity, innovation and the overall success of our business. We do not discriminate on the basis of race, religion, national origin, gender, sexual orientation, gender identity or expression, age, marital status, veteran status, disability status, parental status, genetic history, political affiliation or any other status protected by the laws or regulations in the locations in which we operate.
CompensationThe base pay range for this role is $250,000 – $275,000 per year.