Top Tech Jobs & Startup Jobs in Chicago, IL

Build and own Keycard’s infrastructure platform, including bring-your-own-cloud deployments, multi-tenant and single-tenant cells, infrastructure as code, Kubernetes operations, releases, upgrades, observability, security guardrails, and audited break-glass workflows. Develop tooling and agents for installation, diagnostics, and operational support. Define compatibility matrices, deprecation policies, and upgrade processes while partnering directly with enterprise cloud and security teams.

Own customer relationships from implementation through ongoing operations and expansion. Lead launches, coordinate integrations, manage project plans, monitor service levels, triage issues, deliver reporting and business reviews, analyze outcomes and ROI, identify growth opportunities, and communicate customer feedback to product teams. The role requires customer success or implementation experience, project management, data fluency, LLM familiarity, and HIPAA knowledge.

Own the strategy, roadmap, and execution of AI-powered conversational products across ChatGPT, WhatsApp, RCS, and other platforms. Lead MCP and API integrations, LLM-powered homeowner qualification and contractor matching, messaging journeys, compliance, CRM connectivity, product analytics, and zero-to-one launches. Partner with Engineering, Legal, Marketing, and integration teams to deliver scalable, revenue-generating customer acquisition experiences.

Own a product area end to end, from problem definition and roadmap prioritization through delivery and go-live. Create detailed PRDs, enforce sprint discipline, coordinate engineering, design, quality engineering, customer success, and executives, and translate customer feedback into product improvements. The role requires 0-to-1 product experience, strong documentation, AI-enabled execution, and the ability to lead complex B2B SaaS initiatives across multiple teams.

Lead product strategy, roadmap execution, and measurable outcomes for an AI-enabled refinance title decisioning platform. Translate strategy into requirements, user stories, and acceptance criteria; prioritize initiatives against OKRs; and partner with engineering, data science, operations, sales, and marketing. Monitor product health, accuracy, costs, service levels, and performance through metrics and dashboards. Manage stakeholders, customer onboarding, continuous improvement, and automation opportunities across a regulated real estate workflow.

Supports project and program managers across scope, contracts, schedules, budgets, quality, documentation, procurement, vendor onboarding, equipment logistics, and project transitions. Coordinates data and stakeholder communications, maintains project records and insurance certificates, supports QA/QC documentation, and manages equipment purchasing and inventory. The role requires strong organization, communication, multitasking, project coordination, procurement, logistics, and project management software skills, with 5% to 10% travel to job sites.

Manage federal technology accounts and drive revenue through inside sales, BOM development, quoting, prospecting, opportunity qualification, pipeline management, and solution selling. Build relationships with federal agencies, systems integrators, OEMs, distributors, and partners. Prepare compliant quotes through federal contract vehicles, coordinate internal and external resources, maintain CRM and forecast data, and support opportunities from initial inquiry through award and fulfillment. The role sells cybersecurity, cloud, infrastructure, managed services, and related IT solutions.

Supports daily treasury operations for venture capital and private equity fund clients by processing wires, ACH payments, and other transactions. Maintains payment documentation, reconciles cash activity, prepares reports, uses treasury and banking systems, escalates discrepancies, supports compliance, and collaborates with accounting and internal teams. The role also contributes to process improvements and ad hoc treasury projects while providing strong client service.

Drive new business and revenue growth by selling Cyncly’s SaaS solutions to North American flooring retailers. Manage the full sales cycle from prospecting and pipeline development through proposals, pricing, negotiation, and close. Maintain CRM data, provide accurate forecasts, meet sales targets, and build relationships with C-level stakeholders. The role requires a hunter mentality, strong presentation and decision-making skills, and the ability to work across international teams and cultures.

Build and scale a multi-tenant B2B SaaS product for metal recycling operations. Own data modeling, APIs, UI, UX, deployment, integrations, dashboards, and agentic data features end to end. Collaborate with operators, plant managers, the CTO, and product teams to design workflows, integrate ERP and plant data, and deliver reliable software used on the plant floor. The role is remote within the US with occasional customer-site and company travel.