Top Tech Jobs & Startup Jobs in Chicago, IL

The Associate General Counsel at Orchard will manage legal aspects across various practice areas while focusing on compliance and regulatory matters in real estate, support product innovation, negotiate contracts, and build regulatory relationships.

This job allows applicants to submit their profiles for future operational roles in software engineering, finance, sales, and more. AutoFi offers training and competitive pay.

Handle complex commercial General Liability and casualty claims end-to-end: investigate, analyze coverage, manage litigation, set reserves, attend mediations/trials, communicate with stakeholders, refer fraud/subrogation, and provide guidance to adjusters while ensuring regulatory compliance.

Lead and participate in large-scale process improvement initiatives for provider onboarding and experience. Identify opportunities, analyze root causes, develop and implement solutions, track KPIs, resolve systemwide issues, coordinate cross-divisional stakeholders, provide training, and maintain subject-matter knowledge to support process and system improvements.

Design, build, audit, and optimize Klaviyo lifecycle automations to drive appointment bookings, membership retention, and eCommerce revenue. Create retention, win-back, onboarding, cross-sell, and appointment conversion flows; audit deliverability and segmentation; ensure integrations with Mindbody and Shopify; and report on performance and attribution.

Lead and scale paid mobile acquisition across ASA, Google, Meta, DSPs and other channels. Build measurement systems connecting spend to subscription revenue and LTV, run repeatable testing frameworks, drive creative strategy, use AI to speed reporting and optimization, and establish operating rhythms for budgeting, experiments, and performance forecasting.

Serve as the primary post-sales trusted advisor for enterprise transportation accounts: drive implementation, adoption, retention and renewals; configure and train customers; monitor health and utilization; liaise with Sales, Product, Support and Exec teams; run QBRs and influence product roadmap while managing multiple projects and travel requirements.

Founding iOS Engineer to build the app's core intelligence layer. Must implement production CallKit and on-device continuous Speech Framework recognition, integrate with SwiftUI/CoreData, and optionally add Dynamic Island Live Activity via WidgetKit. Equity-only founding role; product details under NDA.

Build, ship, and maintain agent skills and agentic workflows for Sales, Marketing, Customer Success, and Partnerships. Partner with GTM teams to identify automatable tasks, integrate agents with APIs and data sources, prototype quickly, and own reliability and iterative improvements when workflows break.

Lead Apothekary's creative direction across brand, advertising, packaging, digital and retail. Drive concept-to-execution for campaigns, own photo/video production, manage and mentor internal and external creative teams, track performance and budgets, and collaborate with marketing, product, and digital teams to deliver strategy-led creative that scales the brand.