Top Tech Jobs & Startup Jobs in Chicago, IL

Lead design and delivery of large-scale, cloud-native services powering millions of devices. Architect solutions for scalability and integration, own full service lifecycle in Kubernetes, mentor engineers, participate in on-call support, and drive engineering best practices across cross-functional teams.

Leads the end-to-end customer support organization, owning service-level performance, case resolution, quality assurance, workforce planning, tooling, and operational scalability. Builds technically skilled support teams, career ladders, training systems, and high-performance culture. Partners with Product and Engineering to turn support insights into roadmap improvements and reduce future case volume. Establishes data-driven processes, dashboards, AI-assisted resolution oversight, and strategic operating models for a growing SaaS healthcare platform.

Leads product strategy, roadmap development, prioritization, product metrics, and go-to-market execution for a marketing planning and analytics platform. Manages and coaches product managers while acting as an individual contributor on key initiatives. Partners with the CEO, engineering, sales, marketing, and leadership teams to deliver API-based, data-heavy statistical and machine learning products for technical B2B SaaS customers.

Provides customer onboarding, tier-one technical support, training, troubleshooting, and service coordination for digital dentistry, CAD/CAM, imaging, hardware, and software products. Maintains knowledgebase articles, databases, reports, documentation, and task tracking. Coordinates installations, vendor support, equipment updates, staff assignments, and customer issue escalation while partnering with sales, field technicians, trainers, and internal teams.

Own the full enterprise sales cycle for Fortune 2000 accounts across targeted verticals, from prospecting through negotiation and close. Carry and exceed quota, build qualified pipeline, manage forecasts and Salesforce CRM hygiene, and execute account-based strategies. Navigate complex stakeholder groups, engage executive buyers, represent Trackforce at industry events, and collaborate with Sales Engineering, Customer Success, Product, and Marketing. The role requires disciplined MEDDPICC selling and supports vertical go-to-market initiatives.

Manage property insurance client relationships from onboarding through renewal. Drive product adoption, workflow integration, and measurable outcomes using ZestyAI solutions. Maintain regular client communication, support business reviews, monitor usage and client health, identify expansion opportunities, and relay feedback to internal teams. Collaborate with Product, Risk Analytics, Data Science, Support, Marketing, and senior Client Success leaders while developing expertise in insurance workflows, analytics, and AI-enabled tools.

Own the full B2B sales cycle across the US and Canada, from outbound prospecting through closing, targeting photography studios. Build pipeline, conduct product demonstrations, communicate business value, exceed quotas, navigate objections, and collaborate with a BDR and CRO to develop the North American go-to-market strategy for a SaaS platform.

Own and grow Tiny Health’s healthcare provider sales channel, revenue target, pipeline, and sales team. Build a repeatable sales playbook, improve forecasting and CRM discipline, establish territories and compensation plans, coach representatives, deepen practitioner-segment penetration, and drive recurring account expansion. Partner cross-functionally with Marketing, Product, Science, and Clinical teams while representing the company at strategic accounts, conferences, and industry events.

Build and operate an AI-native software development lifecycle across planning, coding, review, testing, deployment, and incident response. Develop internal AI agents, shared harnesses, CI/CD gates, automated QA, code reviewers, and developer workflows. Embed with engineering teams, ship on their backlogs, drive adoption, remove infrastructure and tooling blockers, and measure improvements in throughput, quality, cycle time, cost, and developer experience.

Lead experience strategy and UX design for digital experiences. Conduct research, define personas and journey maps, facilitate workshops, create wireframes and prototypes, refine information architecture and design systems, support usability testing, and collaborate with cross-functional teams to connect user needs with client business outcomes.