Top Tech Jobs & Startup Jobs in Chicago, IL

Lead SailPoint’s unified Adversary Intelligence organization combining cyber threat intelligence and red team operations. Direct intelligence collection, analysis, adversary emulation, purple teaming, AI-driven automation, custom tool development, strategic risk reporting, executive briefings, and collaboration with SOC, incident response, detection engineering, DevOps, and product security teams. Mentor senior offensive security engineers and intelligence analysts while improving defensive telemetry, detection maturity, and enterprise security posture.

The Staff Machine Learning Engineer will design and build scalable ML systems, mentor engineers, and drive AI strategy at SailPoint, focusing on AI-powered identity security solutions.

Leads technical pre-sales and foundational implementation engagements for SailPoint SaaS solutions. Discovers customer requirements, maps them to product capabilities, delivers proof-of-value implementations, explains architecture and best practices, and collaborates with sales, product, services, and customer success teams. Develops AI and agentic technology solutions for demonstrations and customer problems, while serving as a technical and consultative advisor to customers, partners, and colleagues.

Lead technical customer engagements for strategic accounts, supporting sales, solution design, foundational implementations, and proof-of-value deployments. Discover requirements, map them to SailPoint solutions, educate customers on architecture and best practices, collaborate across sales, product, professional services, and customer success, and develop AI- and agentic-technology solutions for demonstrations and customer outcomes.

Forward Deployed Engineers support sales and customer engagements by discovering requirements, designing and implementing foundational SaaS solutions, delivering proof-of-value implementations, and educating customers on architecture and best practices. They collaborate with sales, product, professional services, and customer success teams; use AI and agentic technologies to solve customer problems; lead technical engagements; document requirements; and develop reusable demonstration solutions. The role may require up to 15% travel.

Manage post-acquisition integration programs and workstreams within SailPoint’s Integration Management Office. Responsibilities include creating integration plans, tracking milestones, dependencies, RAID logs, and TSA deliverables; coordinating cross-functional teams; supporting due diligence and Day 1 readiness; preparing executive status reports; improving integration playbooks; and leading complex integrations while managing budgets, risks, and synergies.

Senior Software Engineer to design and deliver Golang-based microservices, mentor a small pod, estimate and implement features, produce unit and end-to-end tests, collaborate on design and code reviews, improve SDLC, and apply SRE observability practices while working with cloud-scale data stores such as Snowflake, DynamoDB, and Cassandra.

Lead design, build, and deploy scalable, reliable Java-based microservices in a cloud-native, event-driven AWS environment. Own backend feature design, code quality, automated testing, and FedRAMP release processes. Mentor engineers, participate in on-call/TechOps, integrate AI tools into development, and drive architecture, observability, and cross-team initiatives.

Lead pricing strategy and monetization for SailPoint's SaaS portfolio. Develop pricing, packaging, and value-capture initiatives, run customer and willingness-to-pay research, analyze pricing performance, and advise cross-functional and executive stakeholders to improve profitability and win rates.

Manage high-complexity SaaS and software licensing negotiations, draft/customize commercial agreements (SLA, SaaS, SOWs, NDAs, reseller/partner terms), advise Sales/Finance/Security on compliance (ASC 606, GDPR/CCPA), lead CLM and post-execution operations, mentor junior contracts staff, and drive legal-operations efficiency during quarter/year-end close.