Top Tech Jobs & Startup Jobs in Chicago, IL

Owns end-to-end email and SMS campaign execution, including calendar management, creative assembly, segmentation, QA, deployment, reporting, and A/B testing. Analyzes engagement and conversion metrics to optimize campaigns, ensures regulatory compliance, and partners with marketing, creative, merchandising, CRM, and analytics teams. The role also leads adoption of AI tools for campaign workflows and process improvement.

Own end-to-end replenishment for assigned bike categories, generating purchase orders and setting SKU-level inventory parameters. Monitor stock availability, weeks of supply, turns, sell-through, vendor fill rates, late shipments, and excess inventory. Partner with merchants, planners, vendors, and distribution centers to resolve supply issues and improve inventory performance. Build weekly exception reports and enhance tools, automation, and workflows.

Own end-to-end acquisition of net-new B2B trade and hospitality accounts, including prospecting, pitching, closing, pipeline management, and relationship development. Build repeatable AI-powered outreach workflows, maintain CRM discipline, improve forecasting and conversion, and coordinate with merchandising, operations, and vendor teams to support trade clients and special orders.

Own paid media strategy and P&L across a 13-brand portfolio. Lead channel investment across search, social, shopping, display, affiliate, video, and emerging channels; build the performance marketing organization and agency network; improve CAC and media efficiency; establish testing and reporting standards; expand AI and automation adoption; and partner with creative, merchandising, ecommerce, product, and executive leadership.

Own the full B2B group sales cycle from prospecting through close, managing a portfolio and pipeline while meeting revenue targets. Responsibilities include outbound outreach, account growth, customer relationship management, CRM and ERP recordkeeping, coordinating inventory with vendor partners, and developing repeatable sales processes. The role requires independent pipeline management, strong communication, sales training or equivalent experience, and a customer-focused, goal-driven approach.

Conduct outbound prospecting through email, phone, and LinkedIn to generate and qualify B2B group-sales opportunities. Build repeatable campaigns, maintain accurate CRM records, meet pipeline and activity targets, research target accounts, and hand qualified opportunities to Account Managers. The role requires high-volume outreach, strong communication, motivation, coachability, and comfort with sales technology, with a potential path into Account Management.

Own end-to-end executive and specialized recruiting searches across CSC Generation’s portfolio. Source passive candidates through talent mapping, direct outreach, referrals, and LinkedIn; partner with executives to define roles and sourcing strategies; manage confidential searches; close difficult hires; maintain passive talent pipelines; and provide competitive talent market intelligence.

Manage paid customer acquisition and retention across Meta, Pinterest, Google, and potentially TikTok and AppLovin. Own channel budgets, optimize cost-to-performance, and run frequent creative and platform experiments. Use AI to automate reporting, testing, and optimization workflows. Partner across teams to connect marketing systems, explore GEO/AEO, and improve visibility into organic, email, SMS, and social performance.

Own and productize an economics and pricing decision system across inventory states, partnering with data science and engineering to produce daily, auditable pricing recommendations that improve margin and capital efficiency. Lead experimentation, governance, and explainability for pricing, markdowns, and liquidation decisions.

The Head of People Operations will design and lead an AI-driven HR function, developing systems for workforce planning, performance management, and talent development while fostering a high-performing team.