Top Tech Jobs & Startup Jobs in Chicago, IL

Resolve escalated technical issues from frontline support for a SaaS product, provide direct customer solutions, and act as Voice of the Customer to Product and Engineering. Create documentation and troubleshooting resources, work with APIs/JSON/SQL/TCP-IP and issue trackers, and collaborate across teams to improve systems and reduce engineering load.

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.

Lead design and delivery of medium-to-large backend projects, architect scalable distributed systems, mentor engineers, use LLMs and agentic tools to accelerate development, participate in on-call rotations and incident response, and collaborate with Product and Design to build customer-focused solutions.

Build and own full-stack features from design through deployment. Collaborate with product and customers, use AI/LLMs and agentic workflows to accelerate development, mentor teammates, participate in on-call rotations, and maintain reliability through testing, monitoring, and incident response.

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.

Lead and scale an enterprise Customer Success team by building standardized playbooks, QBR cadence, account health metrics, and proactive risk mitigation. Coach CSMs in executive storytelling, strategic selling, and multi-stakeholder account mapping while partnering with Sales and Product to drive renewals, expansion, and product feedback.

Lead the RevOps analytics function: manage an analytics team, own revenue reporting and forecasting, build measurement frameworks, enforce data governance, partner with BI/engineering, analyze funnel and retention metrics, and embed AI/automation to improve revenue predictability and GTM performance.

Own inbound support across Dutchie's POS, ecommerce, payments, loyalty, hardware and integrations. Troubleshoot complex issues, support hardware and compliance workflows, triage payments, use AI-assisted tooling, document tickets, and escalate appropriately while working PST coverage.

The Implementation Strategist at Dutchie manages onboarding and training for new dispensary customers, handling project timelines and customer feedback while collaborating across teams.

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