Top Tech Jobs & Startup Jobs in Chicago, IL

ParentSquare is seeking individuals to join their growing team in enhancing communication tools for schools and parents. The role involves promoting products that engage families and support educators.

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.

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.