Top Tech Jobs & Startup Jobs in Chicago, IL

Lead Testlio’s payments testing strategy, offerings, pricing, and delivery methodology. Design technical quality-engineering approaches for payment architectures, mobile payments, wallets, and POS systems; troubleshoot complex integrations; support enterprise sales and client engagements; guide delivery teams; and develop market-facing content, partnerships, and growth strategies for global payments services.

Freelance testers use their own Apple Vision Pro to perform functional testing of a sporting app during live events. They verify AR/VR elements, identify technical defects, document issues through Testlio’s platform, and complete ad hoc testing tasks of approximately two to three hours. Testing experience is helpful but not required, and training is available. The role is fully remote but limited to specified countries.

Own new business acquisition for enterprise accounts, generating pipeline from scratch and leading complex, multi-stakeholder sales cycles. Build relationships with product, engineering, and QA executives; develop business cases; manage technical evaluations, procurement, legal negotiations, and six-figure deal closures of $300K+ ACV. Target product-led companies, particularly in financial services and retail/B2C software, while partnering with solutions engineering, marketing, and GTM leadership.

Lead architecture, design, and deployment of scalable, production-grade cloud-native services. Define architectural standards, decouple a monolith into modular services, integrate secure AI/LLM patterns, and partner with engineering and product leaders to balance security, cost-efficiency, observability, and long-term scalability.