Top Tech Jobs & Startup Jobs in Chicago, IL

Own the strategy, roadmap, development, and performance of Rivet Education’s digital products, including an implementation dashboard, professional learning guide, and AI products. Research customer needs, define requirements and user experiences, manage external development vendors, prioritize releases, conduct acceptance testing, monitor product and business metrics, and guide pricing and packaging decisions. The role requires strong product leadership, technical fluency, customer insight, and independent execution in a remote environment.

Own the roadmap, modernization, strategy, and growth of merchant onboarding and monitoring products for financial institutions and payment providers. Lead customer transitions, define requirements, prioritize backlogs, collaborate with Engineering and Data Science, evaluate product performance, and support go-to-market readiness. The role requires strong technical fluency in SQL, APIs, data models, AI-enabled solutions, and business-case development, along with customer engagement and cross-functional leadership.

Build and enhance a real-time LLM-powered healthcare platform across the stack. Develop features including onboarding, note customization, and in-the-moment clinical insights. Collaborate with product, design, clinical experts, and go-to-market teams to deliver scalable AI-first applications. Work directly with healthcare providers and contribute to robust engineering practices in a fast-paced startup environment.

Leads the launch of BGO’s enterprise sales motion for its AI-first data operations proposition. Responsibilities include developing prospecting strategy and sales playbooks, generating new-logo pipeline, selling complex $1M+ enterprise solutions, building executive relationships, closing transformational deals, supporting AI/ML product integration, and representing the company at industry events. The role partners with marketing, communications, client solutions, and leadership on RFPs, product roadmap development, and strategic market initiatives.

Serve as the technical and domain authority for complex B2B SaaS sales cycles involving procurement, spend management, and accounts payable automation. Lead consultative discovery, demos, technical scoping, RFPs, security reviews, integrations, and executive presentations. Partner with Account Executives, Product, Marketing, and Customer Success to improve competitive positioning, win rates, sales enablement, and customer handoffs. The role requires strong procurement and AP workflow expertise, ERP integration knowledge, and experience supporting multi-stakeholder deals.

Own and scale Drivetrain’s multi-cloud AWS and GCP infrastructure, Kubernetes platforms, CI/CD pipelines, Terraform modules, automation, observability, and security practices. Drive reliability engineering through capacity planning, incident response, postmortems, and SLI/SLO/SLA management. Partner with development teams to improve application deployability, scalability, resilience, and operational efficiency across the SaaS platform.

Own the entire post-sale client lifecycle: onboard customers, review AI-generated compliance documents, deliver updates from regulatory monitoring, run upsell campaigns, retain and expand accounts, and feed product feedback to the founder. Build processes and define client success at an early-stage SaaS startup.

Owns end-to-end product design for near.com, translating complex financial and cross-chain functionality into intuitive web and mobile experiences. Responsibilities include research, UX and visual design, prototyping, design systems, conversational and AI-powered interfaces, product strategy, and close collaboration with Product, Engineering, and Growth. The role also focuses on building trust, simplifying technical concepts, and delivering production-ready experiences.

Leads the strategy, design, implementation, and measurement of scalable learning and development programs in an enterprise SaaS environment. Responsibilities include employee upskilling, sales enablement, onboarding, leadership development, competency frameworks, learning analytics, change management, and coaching. Partners cross-functionally with HR, People Operations, Sales, Customer Success, and executive leadership to improve workforce effectiveness, engagement, retention, and talent readiness.

Lead customer onboarding and implementation for manufacturing software customers, including process mapping, data migration, configuration, go-live, and user training. Own ongoing customer relationships, drive product adoption, troubleshoot workflow gaps, create custom reports or imports, and communicate product feedback to engineering. The role combines technical problem-solving, process consulting, customer success, and occasional onsite support, with 10–20% travel.