Top Tech Jobs & Startup Jobs in Chicago, IL

Provides Tier 1 technical support and system administration across Windows, Linux, networking, identity, endpoints, Microsoft 365, Azure Virtual Desktop, and customer hosting environments. Responsibilities include ticket triage, incident command, access provisioning, patching, backups and restore testing, security-policy compliance, audit evidence, remote-access administration, troubleshooting, knowledge-base development, and Bash/PowerShell automation. Participates in on-call support and communicates technical issues clearly to users, customers, and executives.

Provides Tier 1 IT support and system administration across Windows and Linux environments. Manages tickets, endpoints, Microsoft 365, identity and access, VPNs, Azure Virtual Desktop, customer hosting support, patching, backups, and incident response. Supports onboarding, audits, access reviews, and privileged credentials while maintaining documentation and automating routine tasks with Bash and PowerShell.

Generate and qualify leads through high-volume outbound calls, emails, and LinkedIn outreach. Follow standardized scripts, research accounts, maintain accurate HubSpot CRM records, route qualified opportunities to Account Executives, and meet meeting and sales-qualified opportunity quotas. Collaborate with sales leadership on call reviews, objection patterns, data quality, and continuous improvement while helping establish Bridgeway’s first SDR function.

Supports cloud infrastructure design, maintenance, monitoring, and automation. Assists with infrastructure as code, CI/CD pipelines, observability, patching, incident response, disaster recovery, security controls, cost optimization, and platform support. Contributes to runbooks, root-cause analysis, documentation, Agile delivery, code reviews, and Tier 2 on-call support while collaborating with development, operations, and security teams.

Lead customer-facing enterprise software implementations from kickoff through go-live and transition to support. Manage project scope, plans, budgets, schedules, resources, risks, forecasts, documentation, stakeholder communications, requirements, proposals, training, and knowledge transfer. Coordinate across professional services, sales, support, engineering, and technical teams to deliver projects on time and within budget while improving implementation processes and portfolio efficiency.

Coordinates full-cycle recruiting for entry- and mid-level roles, including job postings, ATS administration, resume screening, phone screens, interview scheduling, candidate communications, background checks, offer documentation, and onboarding handoffs. Builds university recruiting partnerships, manages recruiting metrics and process documentation, supports inclusive hiring initiatives, and handles vendor administration. The role also provides general Human Capital support and uses generative AI tools to improve recruiting workflows.

Leads compensation, benefits, and HR operations, including merit cycles, pay equity, benefits administration, compliance, vendor management, HRIS data integrity, workforce cost analysis, and process improvement. Advises senior leaders on total rewards strategy, manages an HR Operations Specialist, supports human capital projects, and uses AI tools to improve workflows and productivity.

Leads the ISSI platform engineering organization, owning strategy, execution, budgets, staffing, roadmaps, technical standards, and delivery across multiple teams. Manages engineering leaders, individual contributors, and offshore vendors while partnering with executives on priorities and outcomes. Oversees scalable, secure software delivery, architecture governance, hiring, performance management, process improvement, and adoption of emerging technologies including generative AI.

Own full-cycle net-new enterprise SaaS sales to public sector pension systems, including prospecting, RFP navigation, demonstrations, executive and board presentations, negotiation, and closing. Build territory strategy, manage pipeline and forecasting, navigate state and local procurement, maintain senior stakeholder relationships, and consistently achieve quota. The role requires extensive public sector/SLED sales experience and travel for finalist presentations, conferences, and customer visits.

Leads Scrum delivery across multiple product and platform teams, facilitates ceremonies, removes impediments, mentors Scrum Masters, and drives Agile adoption and continuous improvement. Partners with Product Owners, engineering leaders, and senior management to improve delivery predictability, prioritize backlogs, track metrics, manage risks, and establish consistent processes. Uses Azure DevOps and generative AI tools such as Claude and Copilot to improve productivity and delivery quality.