Top Cannabis Jobs in Chicago, IL

Manage full-cycle recruitment across retail, operations, cultivation, production, and corporate teams. Responsibilities include sourcing candidates, screening, interview coordination, offer extension, pipeline management, recruitment training, employment compliance, employer branding, candidate events, and recruiting metrics. The role requires strong communication, organization, independence, and proficiency with applicant tracking systems in a fast-paced cannabis industry environment.

Supports the legal team with contract lifecycle management, contract drafting and review, records maintenance, M&A due diligence, closing documentation, legal billing, expense accruals, litigation recordkeeping, and cross-functional legal operations projects. The role also manages contract repositories, deal files, legal invoices, and administrative requests while handling confidential information and improving processes.

Designs and maintains scalable data architecture, Snowflake warehouses, ETL/ELT pipelines, dimensional data models, and governance processes. Partners with business stakeholders to deliver insights for pricing, inventory, customer segmentation, and marketing optimization. Builds reliable analytics datasets and dashboards, integrates data tools, monitors data quality, and ensures compliance within the regulated cannabis industry.

Designs, deploys, and maintains AI-driven automation across Accounting and Finance. Automates reconciliations, journal entries, accruals, close processes, and other accounting workflows; integrates ERP, POS, inventory, FP&A, and data warehouse systems; improves data integrity and reporting speed; and leads automation initiatives from pilot through enterprise rollout. The role also establishes standardized frameworks, monitors workflow performance, defines ROI roadmaps, and partners cross-functionally with Finance, IT, and Operations.

The Account Executive will generate and manage sales pipelines, conduct product demonstrations, manage sales cycles from discovery through contract negotiation, and build prospect relationships. Responsibilities include meeting sales targets, forecasting, CRM maintenance, identifying upsell opportunities, and collaborating with business development, marketing, customer success, product, consulting, and implementation teams. The role requires B2B SaaS sales experience, familiarity with HRIS, payroll, or HCM software, and some travel within an East Coast territory.

Manage a portfolio of retailer accounts to collect past-due invoices, negotiate payment plans, resolve disputes, and escalate credit risk. Coordinate with invoicing, operations, and delivery teams, maintain audit-ready records, produce AR/credit reports, and use Slack/Asana/Zendesk and AI tools to streamline workflows and reporting.

Design and build a production multi-agent harness and MCP integrations that operate across ERPs, CRMs, and business tools. Own end-to-end production concerns (reliability, observability, permissions, safe workflow execution), scope the product, make architecture decisions, and ship features working closely with CTO, product, engineering, and design. Stay current with agent frameworks and use tools like Claude Code in development.