Top Tech Jobs & Startup Jobs in Chicago, IL

Build and scale DraftWise's recruiting function from 0->1: own full-cycle hiring (initial focus on GTM), partner with founders and leaders on hiring strategy, source candidates, design recruiting processes and candidate experience, track hiring metrics, support employer branding, and lay groundwork for people operations and future recruiting leadership.

Design and implement front-end features, build high-quality user interfaces, take ownership of product and architecture decisions, collaborate with engineering team, and deliver performant, user-focused solutions.

Senior backend engineer responsible for designing and implementing new features, scaling and optimizing the platform, improving Postgres and Elasticsearch performance, fine-tuning LLMs, and making architectural decisions. Collaborate with engineering team, take ownership of features, write performant, maintainable code, and help shape product and infrastructure for data-intensive applications (NLP, search, indexing).

Own end-to-end client relationships for a book of B2B SaaS customers: drive adoption, engagement, retention, and expansion of AI-powered contract drafting tools. Lead onboarding, training, large-scale rollouts, and translate customer feedback into product improvements while designing scalable CS processes and tracking health metrics to demonstrate value.

Lead technical pre-sales and enterprise rollouts by owning infrastructure strategy, PoCs, migrations (on‑prem to cloud), DMS/CRM integrations, InfoSec discussions, and stakeholder engagement with C-level sponsors to enable scalable deployments and upsell opportunities.