Top Tech Jobs & Startup Jobs in Chicago, IL

Manage the development and delivery of Debit merchant acquiring capabilities, ensuring alignment and effective implementation of product roadmaps across business and technology teams.

Design end-to-end B2B SaaS experiences for restaurants, venues, and internal operations. Lead discovery, prototyping, detailed interaction design, usability research, and iteration. Create artifacts (journeys, flows, wireframes, high-fidelity specs), prototype in Figma and AI tools, partner cross-functionally, contribute to design systems, and improve team processes.

Lead product strategy and execution for Resy consumer and platform experiences across mobile and web. Define and prioritize roadmaps using customer insights and data, partner with design, engineering, and data teams, run experimentation and analytics, and drive measurable outcomes across engagement, retention, and growth while influencing stakeholders and raising product quality.

Lead a consumer product team to define and deliver AI-powered personalization, discovery, search, and retention experiences across iOS, Android, and web. Drive strategy, mentor PMs, embed continuous discovery and experimentation, ship engagement and loyalty mechanics, and raise product craft across the organization with a fast, data-driven, experimental approach.

Drives expansion and cross-selling of B2B payment solutions across strategic existing customers. Builds relationships with procurement, finance, and treasury stakeholders; identifies opportunities; leads sales strategies, negotiations, and pipeline management; and partners with internal SMEs to design and implement payment programs. Oversees supplier management and discusses ERP, procurement, and procure-to-pay integrations with clients.

Provides technical leadership for cybersecurity initiatives protecting Salesforce applications and data. Assesses architectures, integrations, configurations, access controls, and technology changes for security risks; recommends controls and remediation; supports secure engineering standards; and collaborates with cybersecurity, engineering, product, and business teams. The role also mentors colleagues, investigates complex security challenges, evaluates emerging AI-enabled technologies, and promotes secure technology adoption.

Build and operate production-grade agentic AI systems, including orchestration, tool use, structured generation, RAG pipelines, evaluation frameworks, observability, and reliable event-driven services. Lead technical design, establish reliability and rollout standards, evaluate emerging models, and mentor engineers. Collaborate across Product, UX, Data Science, architecture, and engineering teams while shaping shared AI platforms and developer tooling for regulated financial-services environments.

Manages and grows a portfolio of strategic global corporate travel clients. Develops account strategies, executive relationships, business reviews, cross-sell opportunities, and retention plans while partnering cross-functionally across payments, finance, product, technology, risk, legal, and servicing teams. Uses travel agency expertise and financial analysis to optimize payment solutions, profitability, working capital, supplier relationships, and client satisfaction. Leads escalations, projects, and tailored B2B and T&E payment initiatives.

Build and operate production-grade agentic AI services for commercial payments, including orchestration, tool use, structured generation, RAG and embedding pipelines, evaluations, observability, reliability controls, and secure deployment. Collaborate across engineering, product, UX, data science, and architecture teams while contributing to shared AI frameworks and platform tooling. The role requires backend and distributed-systems expertise, strong TypeScript or Go skills, shipped LLM features, and familiarity with event-driven systems.

Acquire new large-market prospects and expand existing American Express customers with more than $300 million in annual revenue. Lead complex consultative sales cycles, sell core and supplier payment solutions, develop growth strategies, meet sales targets, and manage customer setup, card issuance, and signings through the first 19 months. The role requires B2B or fintech sales experience, financial acumen, strong negotiation and presentation skills, and the ability to influence senior executives.