Top Tech Jobs & Startup Jobs in Chicago, IL

Own people operations and full-cycle recruiting for a distributed, multi-state SaaS workforce. Responsibilities include HRIS updates, onboarding, offboarding, employee support, handbook and employment compliance, payroll coordination, technical sourcing, interview coordination, candidate evaluation, offers, ATS management, reporting, and agency partnerships.

Create tax research, calculation, compliance, and evaluation tasks for AI agents. Develop original tax scenarios and reference solutions involving corporate income tax, indirect taxes, withholding, reconciliations, and related areas. Prepare accurate calculations, workpapers, supporting schedules, and authoritative citations. Evaluate agent performance, identify jurisdictional and factual errors, and assess unsupported deductions or outdated rules.

Administers defined benefit pension plans, resolves escalated eligibility, participant data, system, and service issues, and ensures processing quality. Serves as a client and plan-rules subject matter expert, leads change initiatives from discovery through go-live, maintains requirements and process documentation, validates system processing, identifies enhancements, performs peer reviews, and mentors junior analysts.

Leads product management for Perforce’s infrastructure automation platform, owning product vision, strategy, roadmap, lifecycle, and growth. Manages 5–6 senior product managers and partners with Engineering, Sales, Marketing, Customer Success, and Support. Drives customer discovery, product validation, releases, pricing, positioning, compliance, security, and AI-powered capabilities. Provides thought leadership on infrastructure automation, DevOps, open-source models, enterprise deployments, and responsible AI governance.

Supports complex enterprise sales opportunities for agriculture SaaS solutions by partnering with sales teams, demonstrating products, assessing customer requirements, recommending tailored solutions, preparing technical specifications, validating capabilities, addressing objections, and translating technical functionality into business value. Builds trusted customer relationships through consultative engagement, industry expertise, presentations, and value-based storytelling.

Leads regional new-logo enterprise software sales, managing Account Executives and SDR leadership. Owns go-to-market strategy, pipeline generation, forecasting, territory penetration, revenue growth, executive customer engagement, and sales talent development. Partners with Marketing, Presales, Product Management, Professional Services, and Customer Success to sell API management and AI governance solutions.

Develop and maintain Ruby on Rails backend systems supporting solar development, value evaluation, and loan servicing. Responsibilities include writing and reviewing code, maintaining CI/CD pipelines, solving complex domain problems, collaborating with Product and company experts, shaping architecture and technical direction, and improving engineering processes as the company scales.

Own the ongoing technical success of named B2B SaaS customers, guiding integration architecture, implementation, adoption, reliability, migrations, and technical escalations. Partner with account managers, support, product, engineering, and solution engineering to turn customer goals into measurable technical outcomes. Lead customer conversations, incident response, adoption improvements, and on-call participation while maintaining architecture documentation and advancing customer feedback.

Configure and demonstrate Legion’s workforce management platform to prospective enterprise customers. Lead presales discovery, product demonstrations, proof-of-concept engagements, RFP responses, and business justification. Partner with Enterprise Sales to understand customer business and technical needs, communicate platform value, identify risks, and overcome implementation obstacles. Maintain demo environments, contribute to competitive differentiation, and attend field events as needed.

Build offensive red team agents that convert real-world adversary tradecraft into autonomous AI capabilities. Develop attack-chain workflows, payloads, command-and-control, evasion techniques, and post-exploitation skills across Windows, Active Directory, on-premises, cloud, and network environments. Design cyber ranges with production defenses, create measurable security benchmarks, validate attack paths in customer environments, and contribute research to the offensive security community.