Top Tech Jobs & Startup Jobs in Chicago, IL

Manage complex SaaS implementations and enterprise district portfolios, driving engagement, usage, outcomes, renewals, and expansion. Build executive relationships, assess account health, facilitate renewals, provide structured product feedback, document customer challenges, and maintain CRM records. The role requires strong project management, interpersonal, technical, and remote-work skills, with 15–30% travel to customer meetings, trainings, conferences, and company events.

Own end-to-end platform implementations for K-12 school districts, including onboarding, data ingestion, configuration, training, change management, communications, and project tracking. Build rollout plans, lead stakeholder meetings and training, manage timelines and success criteria, maintain implementation records in Gainsight and Salesforce, and proactively address risks. The role partners with district leaders and champions to drive successful, sustained platform adoption and requires 20–25% travel, especially during back-to-school season.

The Controller will own the accounting function, lead the accounting team, and oversee close, financial reporting, GAAP compliance, revenue recognition, audits, internal controls, tax, treasury, cash forecasting, and accounting systems. The role partners with the CFO and FP&A, manages external auditors and banking relationships, improves processes, and scales accounting operations within a venture-backed SaaS company.

Manage a portfolio of smaller school districts by driving product engagement, usage, outcomes, renewals, and expansion. Analyze customer health data, build executive relationships, facilitate renewal processes, provide structured product feedback, document customer challenges, and maintain CRM records. The role requires strong organization, project management, communication, multitasking, proactive problem-solving, and the ability to work remotely and travel approximately 10%.

Own a sales territory by prospecting outbound, building and managing pipeline, accurately forecasting, maintaining Salesforce data, multi-threading K-12 accounts, securing executive sponsorship, navigating public-sector procurement, presenting customer-focused solutions, collaborating cross-functionally, and consistently meeting booking and quota targets.

Oversee end-to-end implementation of Course Planner solutions for school district clients. Manage complex projects, stakeholder relationships, data dependencies, integrations, customer requirements, adoption, and project momentum. Review and resolve data issues, explain technical concepts clearly, document challenges, and collaborate with customer success and product teams on quality assurance and product improvements.