Top Tech Jobs & Startup Jobs in Chicago, IL

Provides frontline technical support for Dutchie’s cannabis retail platform through email, phone, and live chat. Troubleshoots POS, e-commerce, payments, hardware, inventory, integrations, compliance workflows, and AI-enabled tools. Documents cases, resolves urgent customer issues, escalates appropriately, and contributes to internal documentation and platform improvements. Requires customer-facing support experience, strong communication and troubleshooting skills, comfort with web software and CRMs, and availability for evening, weekend, and holiday schedules.

Manage strategic enterprise accounts by developing account plans, driving upsell and cross-sell revenue, building executive relationships, leading complex solution sales, increasing software adoption, negotiating contracts and renewals, forecasting performance, and collaborating with Sales Engineering, Product Management, and Customer Success. The role focuses on enterprise SaaS partnerships and requires strong knowledge of integrations, deployment, security, compliance, and multi-year contracts.

Own the full B2B SaaS sales cycle for Illinois and surrounding Midwestern cannabis markets. Responsibilities include building pipelines, conducting online and in-person demos, managing territory strategies and revenue targets, maintaining Salesforce records, collaborating cross-functionally on launches, and developing expertise in the Illinois cannabis market. The role is remote from Illinois with up to 50% travel.

Own the full B2B sales cycle for Dutchie’s SaaS platform in Northern California. Build and manage a sales pipeline, conduct online and in-person product demonstrations, develop territory strategies, achieve revenue targets, maintain accurate Salesforce records, and collaborate cross-functionally on customer launches. The role requires SaaS experience, strong consultative selling, business acumen, strategic thinking, adaptability, and up to 50% travel.

Lead and coach a team of 4–8 engineers while providing technical direction, architectural oversight, and hands-on coding support. Partner with Product and Design on roadmaps, technical strategy, and delivery improvements. Promote software quality, reliability, and stability; lead incident response and post-mortems; and collaborate with engineering managers and stakeholders to reduce dependencies and support customer success.

Drive technical direction and architecture across teams for enterprise retail software. Improve platform reliability and performance, scope customer-facing features, mentor engineers, de-risk large work, and embed AI-native practices (LLMs/agents) into engineering workflows.

Supports finance and accounting operations involving collections, cash application, payment inquiries, accounts receivable reconciliation, reporting, month-end close, audits, and process improvement. The intern collaborates with cross-functional teams, responds to billing-related Zendesk tickets, investigates payment issues, and helps improve order-to-cash processes. This is a temporary, part-time role of approximately 30 hours per week for a student or recent graduate.