Technical Support Specialist

Technical Support Specialist Reports to: Sr. Engineering Manager 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to accept compliant, cashless payments through direct bank-to-bank (ACH) transfers, eliminating card fees and outdated payment rails.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 highly skilled and collaborative Technical Support Specialist to help stand up and lead our Engineering support function. You will be the primary technical expert bridging our frontline client teams with core Product and Engineering, owning the transition from ad hoc support to a scalable, data-driven practice. This role calls for strong technical troubleshooting skills, a collaborative spirit and a passion for building the dashboards, playbooks and processes our Tier 2 support team will run on. Key Responsibilities: Technical Issue Resolution: Own the #ap-tech-support intake queue for the most complex merchant issues, digging into APIs, webhook configurations and transaction lifecycles to diagnose payment disruptions Lead the use of SQL, Datadog/Kibana logs and internal admin tools to trace failures, identify bugs and verify account setups — and build the initial reporting dashboards for the team Internal Collaboration: Act as the senior gatekeeper for our core Product and Engineering teams, packaging verified software bugs with clear reproduction steps before escalating to Tier 3 engineering Partner directly with the Product function to categorize tickets and prioritize high-impact issues in the engineering sprint roadmap, representing the voice of Tier 2 support Knowledge Management: Build and own the troubleshooting documentation and playbooks that empower our Customer Success (Tier 1) and Solutions Engineering teams Process & Tooling Improvement: Identify patterns in escalations and recommend improvements to tools, alerts and workflows that reduce friction and improve service levels On-call Support & Mentorship: Lead our high-priority P1 response and weekend/after-hours on-call rotation, mentoring teammates on incident handling for critical platform outages Qualifications: 4–6 years of experience in a senior technical support, integration or developer support role, with a strong preference for candidates coming from payment-intensive backgrounds Proven track record building support processes, dashboards or tooling from the ground up Advanced SQL skills for querying across database tables during technical investigations Strong engineering development experience, preferably Python, to trace system behavior across multiple service lines Deep experience troubleshooting API integrations and webhook delivery/client-side integration issues Proficiency with observability tools (Kibana, Datadog, Splunk) and support/ticketing platforms (Jira, Linear, ClickUp, Zendesk) Excellent problem-solving skills and the ability to think critically under pressure Exceptional written and verbal communication skills, with the ability to position complex technical issues to non-technical audiences A strong understanding of payments and financial transactions is highly preferred Ability to thrive in a fast-paced environment with minimal guidance No specific degree required — we care more about curiosity, problem-solving ability and hands-on experience than formal credentials Working Location, Compensation & Benefits: This role is expected to be in office at Aeropay’s Chicago HQ a minimum of three days per week prior to 4/6/26 and Monday through Thursday following 4/6/26 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 $100,000 – $115,000 per year.