Top Tech Jobs & Startup Jobs in Chicago, IL

Leads corporate planning, forecasting, unit economics, scenario analysis, and strategic financial guidance across the enterprise. Partners with executives and functional leaders to optimize resource allocation, acquisition economics, attorney marketplace performance, AI cost of sales, pricing, and cash flow. Oversees operating reviews, multi-year projections, board and investor reporting, and a four-person finance team while driving AI-enabled improvements to forecasting and analytics.

Reviews AI-generated legal and regulatory content for accuracy, completeness, legal reasoning, and jurisdictional relevance. Conducts authoritative legal research, verifies laws and regulatory guidance, identifies errors and unsupported conclusions, and documents structured feedback. Requires expertise in Mainland China or Spain legal systems, strong written English, independent work, attention to detail, and compliance with geographic eligibility requirements. This is a fully remote, freelance project involving approximately 36 hours of work.

Provides practical legal advice on domestic and international employment matters, including employee relations, compliance, investigations, accommodations, wage and hour issues, terminations, agreements, policies, claims, audits, litigation, and immigration initiatives. Partners with HR, leadership, and cross-functional teams to manage risk and support business growth.

Lead application and infrastructure security for LiteLLM, focusing on Python code reviews, vulnerability remediation, threat modeling, secure development tooling, CI/CD and supply-chain security, cloud and IT controls, incident response, and LLM-specific attack testing. Partner closely with engineers to strengthen authentication, authorization, tenant isolation, secrets management, deployment security, monitoring, vulnerability management, and disclosure processes.

Manages relationships with B2B agencies, supports client success, develops new agency partnerships, and collaborates with sales teams on opportunities. Responsibilities include outreach, account support, market research, campaign insights, event coordination, content presentations, and identifying growth opportunities. The role is remote within the United States but requires travel for agency meetings, networking, events, and regional business development.

Build and operate highly scalable Go backend services and data infrastructure for the AT Protocol ecosystem. Scale systems to support hundreds of millions of users, hundreds of millions of events, petabytes of NVMe storage, thousands of CPU cores, and tens of terabytes of RAM. Responsibilities include developing mission-critical services, managing production operations, and working with databases, distributed systems, operating systems, networking, and storage technologies.

Ghostwrite full-length romance and romantasy novels and series installments for Galatea. Responsibilities include reading existing books, developing and pitching story concepts, writing manuscripts, collaborating with authors and AI tools, maintaining continuity, matching house style, incorporating editorial feedback, and meeting regular delivery milestones.

Supports Manhattan Active Omni by troubleshooting user and integration issues, monitoring exceptions, conducting root cause analysis, testing configuration changes and releases, documenting resolutions, and developing user guidance. Collaborates cross-functionally to improve processes, support business initiatives, and enhance customer service. The role also prepares management recaps and continuously expands platform expertise.

Owns strategic relationships with high-value enterprise customers, driving retention, renewals, expansion, adoption, and revenue growth. The role manages executive relationships, success plans, customer health, negotiations, business reviews, and cross-functional issue resolution. Responsibilities include maintaining CRM records, identifying churn risks, building expansion pipeline, and advising customers on complex SaaS and integration environments. The manager must exceed retention and upsell targets while serving as the customer advocate internally.

Own the Databricks enterprise data warehouse and BI solution, designing data models, ETL/ELT pipelines, stored procedures, semantic layers, and governed analytics. Lead healthcare data initiatives supporting value-based care metrics such as HCC, HEDIS, Stars, utilization, MLR, and capitation. Serve as BI product owner, manage roadmap and agile delivery, enforce data quality and HIPAA-aligned controls, and lead a small team while remaining hands-on.