Top Tech Jobs & Startup Jobs in Chicago, IL

Manage end-to-end implementations for strategic (enterprise) customers, develop and execute implementation plans, configure complex B2B SaaS workflows and integrations, drive change management, advise on best practices, measure outcomes with data, and collaborate cross-functionally to ensure timely, successful onboarding and customer value realization.

Provide day-to-day technical support for a complex B2B SaaS product: troubleshoot integrations and configurations, resolve tickets end-to-end, communicate clearly with varied audiences, escalate appropriately, and contribute to projects that improve support workflows and automation. Participate in a rotating schedule requiring one weekend day.

Lead pre-sales scoping and design for enterprise implementations, create and negotiate Statements of Work, ensure smooth Sales-to-Professional Services handoffs, participate in early lifecycle kickoff, refine PS go-to-market motions, and partner with Sales and Solutions Engineering to increase win rates and accelerate time-to-value for enterprise customers.

Lead pre-sales scoping and design for enterprise customers, create Statements of Work, align sales and post-sales teams, participate in handoffs and kickoffs, and improve Professional Services GTM through playbooks and process refinements to increase win rates and speed time-to-value.

Manage end-to-end implementations for strategic (enterprise) customers in a remote-first SaaS environment. Develop and execute implementation plans, drive stakeholder alignment, configure complex workflows and integrations, coach customers through change, and collaborate cross-functionally to ensure timely adoption and value realization. Travel occasionally (<10%) for strategic engagements.

Manage a book of ~20 strategic enterprise customers to drive product adoption, retention, and customer health. Become a product and domain expert, tailor configurations and training, multi-thread across stakeholders, and partner with Sales, Product, Marketing, and Ops to scale playbooks and 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.

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.