Reports to: Head of Revenue

FLSA 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to accept compliant, cashless payments through direct bank-to-bank (ACH) transfers, eliminating card fees and outdated payment rails.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.

Compensation

The base pay range for this role is $130,000 – $140,000 per year.

Aeropay

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Director of Revenue Operations