Top Tech Jobs & Startup Jobs in Chicago, IL

Own and scale sales enablement across the GTM organization, including onboarding, certifications, training calendars, playbooks, coaching, value-selling adoption, and strategic events. Build role-specific development programs, improve content governance, and use AI and performance data to measure readiness, methodology adherence, and business impact. Partner closely with Sales, Sales Engineering, Product Marketing, and GTM leadership in a growth-stage B2B technology environment.

Own product direction, roadmap, priorities, and outcomes for an AI platform serving contractors. Lead customer discovery, product strategy, requirements, launches, measurement, and iteration while partnering closely with leadership, engineering, and customer-facing teams. Make evidence-based product decisions, prototype with AI tools, manage technical tradeoffs, and establish scalable product management practices in an early-stage company.

Owns the operational health, governance, and integrity of customer and prospect data across Salesforce, Marketo, Demandbase, and related GTM systems. Responsibilities include data stewardship, deduplication, enrichment, lifecycle management, integration monitoring, synchronization troubleshooting, segmentation support, data-quality dashboards, process documentation, automation improvements, and audit support. Partners cross-functionally with Revenue Operations, Marketing, Sales, Customer Success, Analytics, and Data Engineering to enable reliable reporting, automation, and AI workflows.

Manages the company’s total rewards strategy, including compensation structures, salary budgeting, incentive plans, employee benefits, regulatory compliance, recognition programs, and wellness initiatives. Leads market benchmarking, open enrollment, vendor management, benefits reconciliation, and employee education. Measures program effectiveness and ROI, develops scalable rewards frameworks, and presents recommendations to HR leadership and executives. Partners across the organization to improve employee experience, attract and retain talent, and ensure rewards programs remain competitive, compliant, and cost-effective.

Own post-go-live relationships for mid-market and enterprise B2B SaaS customers. Drive adoption, configuration refinements, customer health, QBRs, renewals, retention, and expansion. Partner with Sales, Solutions Architecture, Implementation, Product, and Engineering while serving as a strategic advisor to revenue leaders. Build scalable Customer Success playbooks, health scoring, ROI models, and renewal processes as an early team member.

Build scalable simulation and planning systems for complex communications networks. Model hypothetical scenarios, allow users to vary configurations and assumptions, evaluate impacts, compare tradeoffs, identify risks, and integrate simulation capabilities into broader product workflows. The role involves full-stack engineering across design, development, testing, and operations, with emphasis on distributed systems, algorithms, network modeling, and computational reliability.

Serve as the primary general ledger accountant for acquired companies undergoing transition. Clean up accounts, reconcile balance sheets, implement accruals and reclasses, map charts of accounts, support ERP migrations, improve AP and inventory processes, and maintain audit-ready records. Train onsite staff, document procedures, automate manual workflows, support reporting and due diligence, and hand off stabilized accounting operations to ongoing finance teams.

Build and maintain Rocket Money’s Autopilot banking and investment systems. Responsibilities include developing React interfaces and Node.js/GraphQL backends, making architecture decisions, collaborating with stakeholders, managing vendor integrations, improving observability and performance, and owning the technology lifecycle from planning through production maintenance.

Execute B2B SaaS growth campaigns across paid, email, ABM, events, and content syndication. Build HubSpot workflows, landing pages, and advertising campaigns; perform QA; and report on attribution, lead quality, and pipeline contribution. Measure and improve the company’s visibility in AI answer engines through AEO scorecards, content recommendations, page structure, and schema changes. Collaborate with sales, content, and web teams while optimizing campaign performance and budget allocation.

Provide empathetic, high-volume phone and ticket support for trucker customers during evening/overnight ET shifts. Troubleshoot issues in real time using Zendesk, Slack, and internal systems, maintain organization under pressure, and drive excellent customer outcomes.