Top Tech Jobs & Startup Jobs in Chicago, IL

Partner with Ads sales to provide data-driven prospecting, reporting, and strategic recommendations. Build SQL queries and dashboards, produce monthly/quarterly client narratives, run incrementality/A-B tests, and present insights to brands. Support new business pitches, automate reporting workflows, and collaborate with Sales, Ad Ops, and Product on ad performance and product testing.

Leads and scales an enterprise Customer Success team serving high-value retail and cannabis commerce partners. Designs scalable customer journeys, QBR processes, health scoring, account mapping, and churn-risk playbooks. Coaches CSMs in executive communication, strategic selling, and enterprise relationship management. Partners with Sales on renewals, expansion, cross-selling, and account growth, while synthesizing customer feedback for Product and UX teams.

Owns end-to-end launch management for Dutchie’s feature and product releases, coordinating Product, Engineering, Revenue Operations, Marketing, Enablement, Support, and customer teams. Responsibilities include launch planning, risk and dependency management, internal and customer change management, readiness communications, adoption measurement, post-launch analysis, customer feedback, retrospectives, and continuous improvement of launch processes, tools, and automation.

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.

Provides frontline technical support for Dutchie’s POS, ecommerce, payments, loyalty, hardware, integrations, inventory, and compliance products. Handles inbound customer contacts, troubleshoots complex issues, resolves payment and syncing problems, supports hardware and catalog workflows, documents every interaction, uses AI-assisted tools, and escalates unresolved issues appropriately. Requires calm communication during urgent dispensary situations and flexibility for evening, weekend, and holiday shifts.

Supports billing, accounts receivable, collections, cash application, invoice reconciliation, reporting, and month-end close activities. The role investigates billing errors, follows up on overdue accounts, maintains accurate financial records, supports audits, and collaborates with Sales, Customer Success, Implementation, and Business Systems teams. It also contributes to process improvements across the order-to-cash cycle and uses financial software and AI-powered tools to improve operational efficiency.

The Senior Strategic Finance Analyst will conduct strategic analyses, build financial models, and collaborate with various teams to enhance decision-making processes at Dutchie.

Manage a portfolio of customers to drive retention, expansion, upsells, and cross-sells. Build long-term relationships, use data to identify churn risks, coordinate with internal teams to deliver value, and meet revenue targets through strategic account planning and execution.

Lead payments risk efforts by owning Sift and Plaid Signal, designing identity and fraud controls, reducing loss/returns, and running cross-functional risk programs with ACH Operations. Partner with Product and Engineering, perform hands-on analysis using Python and SQL against the data warehouse, and manage a small, growing analyst team.