Top Tech Jobs & Startup Jobs in Chicago, IL

Own the technical vision and architecture for an AI platform of agents, skills, and tools. Scale retrieval/knowledge systems, build developer experience, orchestration, observability, and evaluation/feedback loops. Align cross-division engineering strategy and drive platform adoption.

Manage a book of mid-market accounts post-sale to drive retention and expansion. Identify upsell opportunities, run demos and quarterly business reviews, maintain accurate pipeline and forecasts, use CRM and sales tools, and ensure exceptional client service and documentation.

Design, build, and operate scalable backend services and internal APIs for an AI platform. Integrate LLMs and AI tools into production workflows, ensure platform reliability via observability and incident response, optimize AI runtime performance and cost, and contribute to shared infra like CI/CD and deployments.

Full-cycle enterprise account director responsible for new logo acquisition and quota attainment. Prospect, nurture warm leads, run discovery and demos, close deals, forecast revenue, and manage multiple opportunities using CRM and sales engagement tools. Maintain organization, accuracy in forecasting, and continuous improvement while working in a fast-paced startup environment.

Lead and scale a Value Consulting practice to quantify and prove MaintainX business value for enterprise customers. Partner with Sales, Customer Success, Product, Marketing, and Finance to build ROI and TCO models, drive executive-level business cases, operationalize value realization, standardize success metrics, and influence product and go-to-market messaging. Hire and mentor a team of Value Consultants and support enterprise sales and expansion.

Manage a post-sale book of mid-market accounts to retain and expand revenue. Conduct demos and quarterly business reviews, identify expansion opportunities, maintain CRM and sales systems, forecast pipeline, and deliver high-touch client service in a fast-paced, startup environment.

Manage post-sale book of business for emerging customers (<=300 employees), drive expansion and retention through high-velocity outreach, product demos, forecasting, documentation, and use of sales systems to identify upsell opportunities and ensure client success.

Lead and grow a team of 5–6 product developers to deliver high-quality, reliable software. Partner with product and design, champion CI/CD, testing, observability, and provide visibility to leadership while hiring and mentoring engineers.

Own a post-sale book of emerging (≤300 employees) customers to drive retention and expansion. Manage high-volume, high-velocity deals, prospect for expansion opportunities, present data-driven ROI, run demos, accurately forecast pipeline, document interactions, and use sales systems to support product adoption and client satisfaction.

Lead product experimentation and ML initiatives: design and run A/B tests and causal analyses, build and deploy ML models (GBMs, random forest, logistic regression) using Python and MLflow, partner with Product/Design/Engineering, translate results into executive-facing recommendations, and establish experimentation and ML best practices.