Top Tech Jobs & Startup Jobs in Chicago, IL

The Director of Privacy Design and Governance ensures privacy compliance within product development, advancing a comprehensive program aligned with regulations while providing guidance on data handling, risks, and privacy rights.

Lead and manage a QA team to design and implement QA strategy, automation, and testing frameworks for SaaS and on-prem products. Drive test planning, automation (UI/API), CI integration, metrics reporting, root-cause analysis, and continuous improvement while mentoring engineers and collaborating with cross-functional teams to ensure timely, high-quality releases.

Lead Hireology's IT function for ~200 employees: own cloud and SaaS infrastructure, drive security and SOC 2 readiness, manage vendors and budgets, run the helpdesk, develop a small IT team, and build an IT roadmap aligned to company growth and employee lifecycle workflows.

Own and architect the go-to-market tech stack, acting as primary Salesforce (Sales Cloud) administrator. Manage integrations, data flows, platform health, troubleshooting across systems, vendor evaluations, access provisioning, SOC 2 compliance support, documentation, and stakeholder partnership to streamline lead-to-revenue processes.

Lead credit risk strategy for MyPay including underwriting, limit assignment, loss forecasting, and experimentation. Build predictive models, design and analyze A/B tests, develop dashboards, and collaborate cross-functionally. Manage and mentor a team of Data Analysts to execute analytics and drive risk-informed product decisions.

Build and deploy transformer and sequential deep learning models using large-scale financial and behavioral data to power personalized growth and marketing experiences. Work cross-functionally to design scalable training, serving, and monitoring infrastructure (batch and real-time), contribute to experimentation and optimization frameworks, and maintain production-grade MLOps systems to improve member engagement and business metrics.

Lead regional field marketing strategy and execution to generate demand, accelerate pipeline, and drive revenue. Collaborate with sales, partnerships, and marketing to run events, tradeshows, virtual sessions, and digital campaigns; track performance metrics, provide leadership insights, document best practices, and manage cross-functional initiatives to increase conversions and customer adoption.

Lead and mentor platform engineering teams to design, build, and operate scalable, reliable foundational services. Set technical strategy, drive large-scale initiatives, improve testing and reliability practices, manage platform costs and third-party tools, and participate in incident response and on-call. Collaborate cross-functionally, promote AI-assisted engineering responsibly, and ensure compliance with PCI/SOX/NIST standards while delivering high-quality engineering outcomes.

Lead and manage reliability and maintenance of automated systems and controls, driving uptime, preventative maintenance, root-cause analysis, vendor coordination, safety compliance, and continuous improvement across facility automation assets.

The salesperson will expand existing accounts, acquire new business, and establish strong relationships with clients, focusing on value selling and strategic growth.

Manage and expand a defined portfolio of enterprise accounts through upsell, cross-sell, and multi-product sales. Build executive relationships, develop strategic account plans, drive Operations Cloud adoption, execute complex sales cycles with technical validation, and maintain disciplined forecasting in Salesforce.

Lead pricing and monetization strategy across Gusto's product portfolio. Partner with product, finance, marketing, sales, data science, and engineering to design, launch, and monitor pricing, build AI-powered pricing pilots and MVPs, and drive cross-functional go-to-market execution with executive visibility.

Lead design of complex, cross-team AI-enabled service journeys—mapping systems and handoffs, building AI-assisted service design workflows, enabling practitioners, and improving operational sustainability and measurement.

Founding leader to build Gusto's PEO sales org 0->1 while acting as a player-coach. Design sales motion and Salesforce pipeline, hire and onboard sales talent, develop channel strategy, convert existing payroll customers, plan around PEO selling season, collaborate cross-functionally, use data and AI to drive decisions, and ensure team expertise in PEO compliance and employment regulations.

Lead Solutions Consultant for North America to drive technical and commercial strategy on complex enterprise spend-management deals. Define discovery, demo, and solution design playbooks; mentor and scale the Solutions Consulting team; lead ERP and integration architecture discussions; partner with Sales and Product to align solutions with finance, controls, and audit requirements.

Lead and develop a regional enterprise acquisition sales team to drive new logo wins and expansion revenue. Own territory planning, pipeline and forecast execution (Salesforce), cross-functional GTM strategy, and coaching to meet regional revenue targets while partnering with Marketing, Pre-Sales, Partners, AEs, and Customer Success.