Top Tech Jobs & Startup Jobs in Chicago, IL

Lead end-to-end Revenue Operations for a high-growth B2B SaaS company: build GTM operating model, own forecasting and analytics, manage GTM systems (Salesforce/CPQ/marketing automation), drive AI automation, enable cross-functional alignment, and deliver executive revenue insights to scale enterprise sales.

Develop and maintain software applications on the ServiceNow platform, perform integrations, troubleshoot issues, and communicate with clients.

Lead technical sales cycles for enterprise AI agent deployments: discovery, solution design, demos, POVs, and technical close. Advise on agentic stacks (Databricks, Snowflake), design POVs with success criteria, build technical champions, run architecture reviews, and align technical strategy with commercial goals to drive revenue growth.

Owns revenue operations strategy and GTM planning, including forecasting, annual planning, business reviews, incentive design, analytics, KPI dashboards, and performance insights. Partners with Finance, Product, and Operations to improve sales productivity, align headcount with revenue goals, and execute multi-quarter strategic workstreams. The role translates complex data into leadership recommendations and manages cross-functional projects in a fast-paced environment.

Short-term (8-12 week) contractor role to translate SOX control testing judgment into AI-assisted workflows. Co-develop and prompt AI agents, run and evaluate control tests, document failure modes, design evaluation criteria, and partner with engineering to improve agentic testing.

Outbound-focused BDR responsible for generating qualified meetings for Account Executives through high-volume cold calling and targeted prospecting into healthcare enterprise accounts. Manage an assigned book, maintain CRM data, use prospecting tools, collaborate with cross-functional teams, and meet monthly/quarterly pipeline and meeting targets.

Lead a fully remote team of 25+ Medicare telesales agents to convert high-volume inbound calls into enrollments across Medicare Advantage, Supplement, Part D, vision, and dental products. Provide real-time coaching, monitor conversion and talk-time metrics, manage scheduling across 8am–8pm EST, ensure CMS compliance, partner with Quality/Compliance/WFM, and drive performance during Annual Enrollment Period (AEP).

Identify, validate, and enrich high-confidence license-management leads through open-source research, document forensics, entity validation, and CRM entry. Ensure evidence meets ICP thresholds, collaborate with sales and leadership, and improve targeting through data enrichment and trend analysis.

Produce real-time closed captions by re-speaking into web-based software for live events. Work remotely on project-based assignments, complete training/qualification, perform pre-event checks, and ensure accessibility with clear speech, accurate grammar, and focused, timely captioning.

Support media planning by interpreting campaign performance, building proposals and measurement plans, managing workflows for assigned accounts, acting as day-to-day client contact, and learning integrated digital channels and Basis platform capabilities to drive campaign execution and account growth.