Top Tech Jobs & Startup Jobs in Chicago, IL

Own the company’s business and people operations infrastructure, including utilization, capacity and workforce planning, margin reporting, delivery processes, people operations, tool governance, and AI automation. Manage two operations and recruiting team members, establish operating cadences, improve reporting accuracy, optimize SOPs and workflows, and deploy production AI systems. Partner with executive leadership to support hiring, compensation, profitability, organizational planning, and scalable service delivery.

Own the vision, architecture, roadmap, and execution of AI Teams for enterprise spend management. Design reliable, explainable agent workflows for invoice matching, vendor onboarding, contracts, disputes, and payments. Partner with engineering, data science, UX, and go-to-market teams to build evaluation, observability, training, and feedback systems. Lead customer discovery and technical discussions with Fortune 100 executives, while producing product documentation and demonstrations.

Develop and lead Gainsight’s information security strategy, policies, and procedures. Manage security leadership, architecture, identity management, compliance, risk assessments, vulnerability testing, and threat mitigation. Ensure adherence to GDPR, HIPAA, ISO 27001, SOC 2, and related standards. Present security posture, metrics, and recommendations to executive leadership while collaborating with Engineering, IT, and Security teams in a SaaS environment.

Owns CRM data operations from client discovery through production execution. Responsibilities include documenting CRM structures, profiling and improving data quality, defining warehouse mappings, building actionable segments, coordinating ingestion with engineering and data science, and safely executing bulk loads, extracts, deduplication, upserts, and write-backs. The role requires strong client-facing consulting, CRM administration, data operations, SQL, and mapping documentation skills.

Leads and coaches Regional Account Executives across the Eastern U.S. and Canada while managing a personal portfolio of strategic accounts. Responsibilities include closing enterprise SaaS deals, hiring and developing sellers, inspecting pipelines, owning regional forecasts, building relationships with fire service and public-sector leaders, collaborating cross-functionally, attending industry events, and maintaining accurate CRM activity. The role requires approximately 40–50% regional travel.

Supports daily People team operations across recruiting, onboarding, payroll assistance, benefits administration, employee relations, compliance, HRIS records, training, and employee support. Recruits frontline employees, coordinates background checks and documentation, reviews timekeeping, assists with payroll and open enrollment, maintains policies and compliance reports, and partners with managers on staffing, retention, performance, and engagement initiatives.

Build, launch, monitor, optimize, QA, and report on paid media campaigns across digital advertising platforms. Manage pacing, budgets, audiences, bids, placements, creative trafficking, tracking, and campaign documentation. Analyze performance data, identify issues and opportunities, write actionable insights, support client reporting, coordinate with media partners, and stay current on advertising technologies and best practices.

Analyze marketing and media data to measure TV and streaming campaign effectiveness, validate data and assumptions, identify actionable insights, and create clear visualizations and client-ready presentations. The analyst will use Excel, BI and data platforms, SQL, and AI tools to accelerate analysis while independently validating results and explaining methodologies, KPIs, and recommendations to internal teams and clients.

Build and maintain CI/CD pipelines, cloud infrastructure, Terraform automation, database systems, monitoring, and observability on Google Cloud. Support reliability, security, compliance, incident response, and shared on-call operations while applying backend engineering expertise to production services. The role manages PostgreSQL, Redis, BigQuery, Bigtable, and Firestore environments and contributes to disaster recovery and operational tooling.

Leads user acceptance testing across software releases, including planning, test scenarios, tester coordination, defect tracking, triage, sign-off, and release readiness reporting. Independently performs business analysis for smaller initiatives by facilitating requirements discovery, documenting user stories and acceptance criteria, coordinating stakeholders, and validating delivered solutions. Maintains requirements and UAT documentation, supports Agile ceremonies, and drives cross-functional activities to resolution.