Top Tech Jobs & Startup Jobs in Chicago, IL

Reviews account activity and payment approval requests, investigates suspicious activity and fraud patterns, and makes risk-based approval or escalation decisions using AI-assisted analysis. The role supports compliance operations, improves processes, documents findings, and collaborates with product, support, and business teams to balance compliance, customer experience, and scalable growth.

Own the Commercial sales pipeline from discovery through close, converting inbound demand and building outbound opportunities. Manage multiple opportunities, maintain accurate forecasts and CRM records, run efficient sales cycles, and partner with SDRs, Marketing, and Customer Success. The role also involves identifying successful deal patterns, improving the sales process, and consistently achieving revenue targets in a fully remote environment.

Own product foundations across Tremendous, improving navigation, information architecture, design systems, motion, micro-interactions, and overall product craft. Set a product foundations vision, document reusable patterns, support projects without embedded designers, and partner with engineering to prototype and ship polished experiences. The role requires strong B2B product design experience, visual and interaction design craft, product thinking, communication, and AI-assisted prototyping.

Own end-to-end people operations for a fully remote, international company. Responsibilities include HRIS and benefits administration, onboarding and offboarding, policies and documentation, workplace investigations, performance and compensation cycles, employee support, international employment models, and employment-based immigration matters. The role will establish the company’s first dedicated people function and manage US, Canadian, and international employee programs.

Own the growth product experience from first touch through first reward, focusing on signup, onboarding, conversion, activation, acquisition channels, incentives, and self-serve customers. Build the growth roadmap, establish experimentation and landing-page systems, collaborate with Marketing and RevOps, prototype with AI, and help staff a new cross-functional squad in a fully remote, documentation-first environment.

Outbound-focused Sales Development Representative responsible for securing meetings with target accounts via outbound prospecting, social selling, networking, and events. Collaborate with Account Executives, Marketing, and Customer Success, use Outreach/LinkedIn and other prospecting tools to research contacts, craft targeted messaging, and communicate product value to drive pipeline and revenue growth.

As an Engineering Manager, you'll lead and develop an engineering team, ensuring technical quality, fostering growth, and guiding product initiatives, while utilizing AI effectively.

The Senior Product Manager will lead the Prepaid Cards team, managing cardholder journeys, product roadmap, and collaborating across technical partners while ensuring effective solutions and communication in a remote work environment.

Own the Platform product end-to-end: prioritize and manage roadmap for infrastructure, security, AI infra, data/compliance, and internal tooling. Collaborate closely with engineers and designers to frame problems, run research, define requirements, and measure post-release impact. Operate in an async, documentation-first culture and influence stakeholders to drive technical decisions and ship complex systems.

Build reliable data models and semantic layer for AI-powered analyses. Support Product, Finance, and Customer Success with SQL-based analytics, BI dashboards, and stakeholder storytelling. Standardize data team processes, prioritize work, and collaborate across company to enable data-informed decisions.