Top Tech Jobs & Startup Jobs in Chicago, IL

Lead and scale a Support Engineering function for Ashby across the Americas. Own vision, operating model, escalation/triage standards, reporting, tooling, and cross-functional feedback with Product and Engineering. Manage a Support Engineering Manager, drive hiring and career paths, and use data to reduce recurring technical friction while balancing immediate customer resolution with durable product improvements.

Lead and coach a team of Customer Success Managers to drive adoption, retention, and long-term value for a large portfolio. Build repeatable playbooks, scalable processes, and operational rigor. Partner cross-functionally (Implementation, Support, Sales, Product) to ensure seamless lifecycle experiences, use data to inform decisions, and continuously improve team performance and customer outcomes.

Lead and grow a Support Engineering team that resolves complex product issues, integrations, and data workflows. Define escalation and triage practices, build scalable diagnostics and internal tools, collaborate closely with Engineering and Product, mentor engineers on debugging, logs, and database querying, and create repeatable processes to improve customer outcomes and support efficiency.

Provide technical troubleshooting for customer issues, focusing on API integrations, data flow, and automation via scripting. Collaborate with engineering to escalate and resolve bugs, identify patterns to drive product improvements, maintain support documentation, and enable the Support team through knowledge sharing and process improvements.

Lead end-to-end implementations for mid-market B2B SaaS customers (≈15 concurrent projects, 4–8 weeks each). Develop and execute implementation plans, manage stakeholders, provide technical configuration guidance, drive change management, advise on best practices, and collaborate cross-functionally to ensure timely customer value and adoption.

Lead and develop a global team managing SaaS renewals and complex contract negotiations. Build scalable renewal processes, improve forecasting and CRM hygiene, partner cross-functionally with Sales, RevOps, Legal, Finance and Product, and translate negotiation outcomes into playbooks to drive retention and commercial growth.

Lead and grow a Mid-Market Solutions Engineering team: hire, coach, and operationalize demo, trial, and RFP processes; partner with sales leadership to accelerate deals; build scalable systems, feedback loops, and enablement to drive revenue and product insights.

Lead and scale an enterprise Solutions Engineering team to win complex SaaS deals. Hire and coach SEs, drive technical deal execution (demos, POCs, security reviews, RFPs), build scalable processes and enablement, partner with Product/Engineering and Sales, and lead strategic initiatives from diagnosis through implementation to impact revenue and product direction.

Own end-to-end sourcing for Sales/GTM hires at a high-growth B2B SaaS company: build passive pipelines, discover new talent pools, qualify requirements with hiring managers, conduct high-volume outreach and screening, and deliver high-quality, data-informed candidate slates.

Provide hands-on commercial contracting support focused on sales (NDAs, MSAs, Order Forms, DPAs) and procurement; draft, review, and negotiate contracts; build scalable processes, playbooks, CLM/CPQ workflows, and sales enablement; partner with Sales, Security, IT, Product, and Legal Ops to answer questionnaires, drive tool adoption, and support growth-stage scaling.