Top Tech Jobs & Startup Jobs in Chicago, IL

Lead strategic legal AI pilots and research projects from scoping through operationalization. Define legal quality, feasibility, cost, workflows, expert requirements, quality standards, and scalable delivery models. Apply legal judgment to case law, contracts, statutes, regulatory filings, and legal reasoning while addressing privilege, confidentiality, and jurisdictional requirements. Partner with customers, researchers, attorneys, legal experts, and global delivery teams to validate and scale successful programs.

Own the full sales cycle for AI brain-analysis software across U.S. hospitals, clinics, medical centers, and physician practices. Build self-generated pipelines, manage complex healthcare technology sales, conduct technical and clinical demonstrations, forecast and quote opportunities, onboard customers, and develop strategic partnerships and channel networks. Generate leads through conferences and digital channels, communicate ROI and reimbursement strategies, gather customer feedback, and travel nationally for meetings, demonstrations, conferences, and training.

Own the end-to-end revenue and billing cycle for subscription, usage-based, and outcome-based contracts. Responsibilities include invoicing, ASC 606 revenue recognition, deferred revenue schedules, month-end close, reconciliations, commission capitalization, accounts receivable, collections, customer billing support, contract review, and reporting. The role also improves quote-to-cash processes across NetSuite and Tabs, maintains controls, and supports audits.

Generate and qualify new leads through high-volume outbound calls, cold outreach, email cadences, and campaign follow-up. Engage dental providers and office managers, identify workflow pain points, communicate the value of Archy’s SaaS platform, and schedule demonstrations for Sales Executives. Use AI tools, CRM systems, and sales automation to improve prospecting efficiency. Collaborate remotely with Sales and Marketing teams while meeting activity, dialing, and demo-booking KPIs.

Build, optimize, and deploy machine learning models (especially time series) using Python, PySpark, and cloud tools. Perform feature engineering, evaluate model performance (MAPE, RMSE, R²), and create ETL/data pipelines with integration tools. Work with Palantir Foundry, Google Cloud (BigQuery, Vertex AI), AutoAI, and data warehouses to support large-scale analytics. Collaborate with stakeholders, monitor production models, and continuously improve model accuracy and pipelines.

Lead the global accounting function and team of approximately seven, overseeing close, general ledger, AP/AR, payroll, treasury, revenue recognition, equity compensation, controls, audits, tax coordination, and international compliance. Improve close timelines and reconciliation quality, author technical accounting memos, maintain audit-ready books, and drive automation across NetSuite and connected finance systems. Partner with senior stakeholders across the company while scaling accounting operations for a remote-first, multi-currency subscription business.

Implements, configures, and maintains cybersecurity, networking, and cloud technologies for clients. Assesses environments against security frameworks, administers networks, monitors events, investigates suspicious activity, develops SIEM detections, troubleshoots technical issues, documents procedures, and supports client projects. The role collaborates with SOC and other teams while delivering secure solutions and client-facing managed security services.

Supports cyber underwriters throughout the policy lifecycle, including new business quotes, renewals, endorsements, referrals, documentation, file maintenance, and policy issuance. Communicates with brokers, insureds, customers, underwriters, sales teams, and internal departments to resolve issues and gather account information. Maintains underwriting standards, completes administrative tasks, supports compliance training, and assists with ad hoc projects. Requires cyber insurance experience, cybersecurity knowledge, strong organization, communication, and Microsoft Office skills.

Lead enterprise sales skills training strategy—diagnose skill gaps, design and deliver instructor-led and virtual practice-based learning, create leader reinforcement toolkits, operationalize post-training reinforcement, measure effectiveness, and partner with Sales leadership to drive measurable sales outcomes.

Manage a portfolio of Tier 3 clients, building relationships, improving retention, and driving revenue growth through upselling and cross-selling fleet solutions. Responsibilities include forecasting vehicle orders, maintaining the Salesforce pipeline, presenting client scorecards, identifying at-risk accounts, and collaborating with internal teams on onboarding and strategic initiatives. The role is remote with occasional travel for high-value client meetings and events.