Director of Revenue Operations in Chicago, Illinois at Aeropay

Director of Revenue Operations
Reports to: Head of RevenueFLSA 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to accept compliant, cashless payments through direct bank-to-bank (ACH) transfers, eliminating card fees and outdated payment rails.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:
Aeropay is seeking a hands-on Director of Revenue Operations to serve as the operating partner to the Head of Revenue, driving sales enablement, inbound lead quality, pipeline forecasting and a performance culture across the Revenue org, while also owning pricing, commercial agreements and Tier 1 client negotiations. This isn't a role for someone who only administers a CRM — the right person moves comfortably between strategy and execution, challenges assumptions with data and personally delivers the analysis and system changes the business needs, including the HubSpot systems that support the team. This role directly shapes how Aeropay allocates resources, prices opportunities, evaluates risk, compensates our team and commits revenue to the board, all with high expectations for ownership.
Key Responsibilities:
Sales Enablement, Pipeline Oversight & Forecasting:

• Own sales enablement materials, inbound lead automation and lead quality, partnering closely with Marketing to improve conversion
• Build the pipeline forecast and operating cadence with Finance (pipeline inspection, stage definitions, probability methodology, scenario planning), translating bookings, transaction volume, pricing and ramp assumptions into credible projections
• Build board-ready reporting on performance, risk and variance, flag coverage and conversion gaps before they become missed targets and drive a performance culture across the Revenue team

Pricing, Commercial Agreements & Partnerships:

• Own pricing frameworks, deal modeling and commercial guardrails, sitting at the table for Tier 1 commercial negotiations and contract terms
• Build deal models (volume ramps, transaction mix, risk exposure, contract terms, partner economics, contribution margin) and support complex opportunities with scenario analysis and clear recommendations
• Support Partnerships on revenue-share structures and multi-party commercial models

HubSpot Administration & AI Automation:

• Administer HubSpot Sales Hub, Marketing Hub and Service Hub (architecture, governance, permissions, integrations), keeping the platform as self-service as possible while preserving white-glove support for Tier 1 accounts
• Design lifecycle stages, pipelines, workflows, lead routing, scoring and attribution, and build automated journeys from initial engagement through expanded revenue
• Make AI a practical part of the Revenue org (prospect research, lead qualification, forecasting, service workflows), replacing repetitive work with reliable automation

Commissions & Compensation Operations:

• Run the end-to-end commission process (calculations, approvals, statements, dispute resolution, payroll handoff) and maintain plan documentation and an auditable decision-making record
• Model compensation plan changes and recommend structures that align performance with company goals

Qualifications:

• 10+ years of experience in revenue or sales operations in B2B SaaS
• Proven ability to develop sales enablement, inbound lead automation and foster a performance culture
• Demonstrated ownership of pricing, commercial agreements and deal modeling, ideally including Tier 1 or enterprise negotiations; experience with partner and channel economics or multi-party models is a plus
• Expert HubSpot experience in Sales, Marketing and Service Hubs, covering architecture, automation, reporting, governance and integrations
• An AI-native operating mindset demonstrated by building workflows, agents or automations that enhance speed, quality, conversion and team capacity
• Advanced financial and analytical skills, including strong spreadsheet modeling and the ability to translate analysis into recommendations; familiarity with BI tools, SQL or data warehouses is a plus
• Deeply data-driven, detail-oriented and able to develop repeatable, auditable processes efficiently
• Executive communication skills and confidence to challenge assumptions and hold leaders accountable
• A builder mindset: comfortable defining the strategy and doing the work yourself
• Experience supporting a product-led, self-service motion, with the judgment to qualify leads

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: $130k - $140k 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 $130,000 – $140,000 per year.