Top Tech Jobs & Startup Jobs in Chicago, IL

Drive B2B SaaS cybersecurity sales across the Chicago/Midwest territory by owning the full sales cycle, building pipeline, prospecting, conducting tailored demos, negotiating, and closing new business. Develop account strategies, engage CIO and CISO stakeholders, collaborate with Marketing, Product, and Customer Success, represent the company at customer meetings and events, and help establish repeatable sales processes in a startup environment.

Lead and grow a 16-person engineering organization across four AI-focused pods. Set technical direction, guide AI-native product and engineering development, manage cross-team dependencies, and oversee delivery, quality, reliability, security, and velocity. Partner with product, design, and leadership on scalable full-stack systems, mentor engineers and technical leads, and promote strong practices in architecture, testing, observability, incident response, and CI/CD within a HIPAA/SOC 2-aware environment.

Supports leaders and employees across North America on employee relations, performance management, HR operations, leave administration, compliance, onboarding, HRIS updates, reporting, training, engagement, and employee communications. The role partners with managers, maintains employment records, coordinates accommodations and leave processes, supports recruitment and performance programs, and delivers practical HR solutions while improving employee experience and data integrity.

Sell international educational travel programs to schools, teachers, and students. Responsibilities include prospecting, developing new and existing business, managing sales pipelines and cycles, assessing client needs, preparing proposals, closing opportunities, meeting sales targets, and contributing market feedback and sales strategies.

Generate and qualify manufacturing leads through outbound calls, emails, text messages, and LinkedIn. Research target accounts, identify decision-makers, schedule qualified demonstrations, maintain prospect data, and partner with Solution Architects to build enterprise pipeline and close deals. Meet activity and demonstration quotas while maintaining accurate CRM records and following defined sales processes.

Develop new software business across SMB, mid-market, and enterprise segments. Own the full sales cycle from outbound prospecting, qualification, discovery, solution positioning, demonstrations, negotiation, and closing. Build and manage qualified pipeline, maintain accurate HubSpot forecasts, develop account strategies, engage decision-makers, collaborate cross-functionally, and provide market feedback. Help refine sales messaging, qualification standards, outbound strategies, and go-to-market processes in a growing business.

Provide analytics, automation, and reporting to support compliance testing and monitoring. Collect, validate, reconcile, and analyze large data populations; develop repeatable testing routines, dashboards, and automated solutions; support sampling, exception analysis, reporting, and stakeholder requests to identify trends, risks, and remediation status.

Leads and independently delivers complex control system integration projects, including design, instrumentation specifications, HMI and PLC applications, IT and network infrastructure, commissioning, budgeting, scheduling, risk management, and customer communication. Mentors team members, oversees project-site personnel when needed, ensures quality and customer satisfaction, and may participate in on-call rotations and overnight travel up to 50%.

Lead enterprise-scale migrations to GitHub Enterprise Cloud, including repositories, users, access controls, workflows, Enterprise Managed Users, and data residency. Build governed identity and access environments, validate integrations, and document handoffs. Design and maintain scalable internal developer platforms, standardize tooling, and develop self-service infrastructure and CI/CD capabilities. Partner with client IT teams, mentor engineers, and apply cloud-native architecture, Kubernetes, automation, and Infrastructure as Code practices.

Leads and develops a team of Conversion Data Analysts, owning workload prioritization, delivery quality, and performance outcomes. Uses KPIs and data to identify risks, guide decisions, and improve high-volume conversion workflows. Partners with project management, Engineering, Product, Support, and leadership to ensure accurate data mapping and successful customer onboarding. Requires people leadership, SQL, Excel, data validation, CRM, and conversion tooling experience.