Top Tech Jobs & Startup Jobs in Chicago, IL

Lead technical strategy and architecture as a Principal Software Engineer, define company-wide AI/LLM roadmap, drive platform reliability at scale, mentor senior engineers, and partner with executives and product to deliver secure, high-impact solutions.

Manage and grow organizational partner relationships to drive leads and product adoption. Coordinate partner marketing, enable sales with partner-related materials, assist finance with partner reporting, collaborate cross-functionally (sales, marketing, customer success), and identify and onboard new partnership opportunities to enhance ParentSquare usage.

ParentSquare seeks a Revenue Operations Specialist to manage lifecycle strategy and automation, enhance customer engagement, and optimize go-to-market processes using HubSpot.

Develop and ship backend and frontend features that improve school-family communication. Collaborate with product and design, champion AI/LLM-driven workflows, build scalable secure services on AWS, evolve monolithic systems, participate in code reviews, and help shape architecture.

Own a product line end-to-end: strategy, growth, retention, unit economics, and margin. Lead discovery, shape high-stakes bets, pitch leadership, and drive cross-functional execution. Partner with platform and Data/AI teams to build responsible AI workflows and scalable delivery while protecting engineering appetite and outcomes.

Lead and grow a remote Implementation team (5-7) to onboard SmartSites customers, oversee site builds/configuration/training, ensure timely project delivery and high customer satisfaction, coordinate cross-functional training, handle escalations, and support Customer Support during high volume periods.

Serve as an HR partner supporting full employee lifecycle and daily People operations. Build and maintain processes for talent acquisition, onboarding, benefits administration, HRIS/ATS accuracy, learning and development, performance management, and compliance. Act as first-line support and point of contact for employees, lead new-hire orientation, and help sustain an inclusive remote culture while partnering across teams to attract and retain talent.

The Staff Engineer will lead cross-functional teams, focus on AI development practices, ensure scalable engineering, and evolve system architecture at ParentSquare.

Lead post-sale implementations for multiple K-12/EdTech clients: manage data integration, system configuration, initial admin training, documentation, CRM updates, troubleshooting/escalation, and handoff to customer support while maintaining high satisfaction and implementation metrics.

Manage and mentor an engineering squad while contributing technically. Own delivery, sprint execution, KPIs, hiring, security, reliability, and advocate AI-assisted development to accelerate engineering productivity.