Top Tech Jobs & Startup Jobs in Chicago, IL

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.

Lead and build a Strategic Customer Success team, design high-touch success programs and playbooks, coach CSMs into consultative executive partners, define adoption and retention metrics, synthesize account insights into product feedback, partner cross-functionally, and experiment to create a scalable strategic CS motion for a multi-product AI productivity suite.

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.

Own and improve global HR operations across employee lifecycle, HRIS data quality, leave and benefits administration, workflow automation, reporting, compliance tracking, and cross-functional process optimization.

Lead and scale a Quality Assurance team that validates and qualifies open-source leads for sales readiness. Own hiring, training, QA standards, KPI tracking, and process improvements while partnering with SDRs, Sales, and partners to drive pipeline impact.

Architect and validate technical solutions for major enterprise accounts, lead the technical sales process, run end-to-end Proofs of Value, and collaborate with internal teams to resolve critical customer security challenges.

Manage high-volume contract renewals for commercial customers (<= $50K ARR), drive on-time renewals through cross-functional collaboration, identify upsell opportunities, and adopt AI tools to increase productivity and meet targets.

Manage a high-performing software engineering team, driving product roadmap and technical direction, while ensuring quality, performance, and innovation.

As a Lead Infrastructure Engineer, you'll enhance database reliability, automate infrastructure, collaborate on initiatives, and participate in on-call duties.

Lead full‑stack engineering efforts to design, build, and operate production healthcare systems. Own epic-level features, mentor engineers, design for reliability and scalability, integrate with partners, and ensure launch readiness across backend (Java/Groovy), frontend (React/TypeScript), data (MongoDB), and event-driven pipelines (Kafka).

Lead Modo's community and reputation across Discord, Reddit, Trustpilot, and app stores. Build and moderate communities, design reputation systems and response playbooks, surface player insights to Product and Marketing, drive member activation into events and tournaments, and report on community and reputation health to leadership.