Top Tech Jobs & Startup Jobs in Chicago, IL

Perform advanced offensive security work: conduct complex penetration tests, teach and integrate offensive tradecraft into the AI platform, harden product and company defenses, and collaborate with core engineers to build and ship capabilities that automate red-team techniques.

Manage marketing-generated leads, qualify and route prospects, maintain CRM data quality, support outbound campaigns and eCommerce customer onboarding, and coordinate cross-functional stakeholders to accelerate opportunities and improve commercial processes.

Own technical onboarding, content ingestion, widget configuration, and post-launch partner support. Triage and reproduce issues, optimize AI answer relevance via prompt/config tuning, maintain onboarding/docs and SLAs, and collaborate with Engineering, Product, and Partnerships to scale partner implementations and reduce recurring support work.

Lead product positioning, messaging, and GTM for agency- and carrier-focused products. Coordinate launches, create marketing assets, support campaigns, and enable sales/support with training and research to drive awareness, adoption, and product-market fit in a fast-growing insurtech startup.

Lead net-new enterprise business development across the UK and Europe for Infrastructure Management & Security Services. Drive $5M-$10M annual revenue by sourcing opportunities, building executive relationships (CIO/CTO/CISO), managing full sales lifecycle, and closing complex IT transformation engagements (IMSS, Cloud, Cybersecurity, Digital Workplace). Develop go-to-market plans, partner with cloud/OEM alliances, lead proposals and negotiations, and expand presence across target verticals.

Perform application-security engineering: run SAST/DAST scans, triage and remediate vulnerabilities, integrate Fortify/JFrog Xray/OWASP ZAP into CI/CD, support software-supply-chain/SCA efforts, and collaborate with developers to document and resolve security findings.

Serve as a trusted advisor to enterprise customers to design and execute multi-quarter SEO and GEO strategies. Lead discovery, opportunity analysis, and executive roadmaps; design governance and operating models; facilitate workshops and executive briefings; track KPIs and risks; partner cross-functionally with Sales, Customer Success, and Product to drive adoption and long-term growth. Contribute to internal playbooks and methodology improvements.

First-line participant support for retirement accounts via Intercom and phone; guide account setup, enrollments, deferrals, rollovers, withdrawals, and loans; resolve issues end-to-end and escalate when needed; build support content and AI-powered tooling; coordinate money movements and external custodial/vendor partners; surface recurring problems to product and engineering; own support quality, response times, and tone.

Provide phone, chat, and ticket-based support for grocery stores using an iOS POS. Troubleshoot iPad terminals and peripherals, resolve POS workflows and payment issues, document incidents, escalate complex problems, collaborate with onboarding/installation teams, and relay recurring issues to product and support leadership.

Serve as primary client contact for a portfolio of loyalty-program clients. Scope and manage end-to-end actuarial analyses rooted in predictive modeling and machine learning, validate model outputs, translate results into clear recommendations and presentations, and partner with analysts and data scientists to deliver high-quality, client-facing work in a fully remote consulting environment.