Top Tech Jobs & Startup Jobs in Chicago, IL

Provides Level II helpdesk support for employees and contractors, handling tickets, user administration, desktop support, licensing, hardware requests, VIP issues, asset tracking, audits, maintenance, patching, and escalations. The role also supports special projects, product and service ownership, networking, telephony, and unexpected technical issues. Requires three years of similar helpdesk experience and working knowledge of Okta, Google Workspace, Mac, Windows, hardware, and networking technologies.

Own the Merchant Dashboard product strategy, roadmap, information architecture, interaction patterns, personalization, and monetization surfaces. Partner with Engineering, Design, Marketing, Data Science, and GTM teams to deliver scalable solutions. Analyze customer feedback, market trends, competitive offerings, and product data to identify opportunities. Lead experimentation, prioritize initiatives, communicate product vision, and advocate for merchant needs across the organization.

Own SpotOn’s end-to-end payments product strategy and roadmap across card-present and card-not-present transactions. Lead payment acceptance, processing, settlement, funding, routing, risk, and merchant-facing experiences. Improve authorization, resiliency, chargebacks, reconciliation, and funding accuracy through data-driven experimentation. Partner with engineering, design, compliance, security, operations, GTM, processors, acquirers, gateways, and networks to deliver compliant payment capabilities and guide cross-functional execution.

Leads Intelligence, Reporting, and AI product teams; defines product strategy, vision, and roadmaps; manages and coaches Product Managers; uses customer research, metrics, market analysis, and emerging technologies to guide decisions; and partners with Engineering, Design, Sales, Support, executives, investors, and restaurant customers to deliver impactful products.

Design and deliver engaging in-person and remote training for restaurant clients on SpotOn POS and related software. Create user guides, videos, and interactive materials; host Q&A and facilitate participation; document session feedback and update resources to reflect software changes and client needs.

Own the end-to-end onboarding for enterprise and mid-market multi-location clients, managing technical configuration, integrations, timelines, stakeholder communications, testing, documentation, and KPIs to ensure successful POS activation and client adoption.

The Client Onboarding Manager oversees a team to enhance client onboarding experiences, ensuring timely project execution, team performance, and client satisfaction through effective leadership and process improvements.

Design, develop, and maintain Android point-of-sale software for high-availability, real-time restaurant systems focused on payments. Collaborate with product, design, and backend teams to deliver features, ensure quality through testing and code reviews, and address complex technical challenges. Provide technical leadership and mentorship while contributing to subsystem design focused on scalability, security, and performance.