Top Tech Jobs & Startup Jobs in Chicago, IL

The Director of Contractor Operations will build systems for team growth, drive employee engagement and retention, and ensure alignment with business objectives.

Lead global recruiting and people operations for a remote, contractor-centric education brand. Build sourcing pipelines, run structured interviews and test projects, manage employer brand and hiring metrics, and design scalable people systems (onboarding, performance, org design) to support growth toward $100M.

Lead full finance function: deliver monthly audit-ready financials, maintain weekly 12-month cash forecast, own budgeting/forecasting, implement automated systems, create SOPs, produce dashboards, partner with leadership to improve profitability and scale finance systems.

The Director of People Systems & Strategy at Hadley Designs will develop scalable people systems, enhance talent management, and foster organizational growth. Responsibilities include leading talent acquisition, optimizing workforce planning, establishing performance frameworks, and improving employee engagement and retention.

Lead global talent acquisition and people operations for a remote, contractor-centric company. Build scalable recruiting pipelines, run structured interviews and test projects, manage employer brand, deliver hiring metrics, and design people systems for onboarding, performance, retention, and organizational design to support growth toward $100M.

Lead full finance function: deliver timely, audit-ready monthly financials; maintain weekly 12-month cash forecast; own budgeting, forecasting, and financial modeling; implement automation and systems (ERP, reporting); document SOPs; drive profitability and EBITDA improvements; partner cross-functionally on inventory, cash, and product planning.

Lead the finance function at Hadley Designs by building scalable systems, managing cash flow, and driving profitability to support growth.

Lead global recruiting and people operations for a remote, contractor-centric e-commerce brand: build sourcing pipelines, run structured interviews and test projects, manage employer brand, deliver hiring metrics, and design scalable people systems for onboarding, performance, and retention.

Lead talent acquisition and people operations for a remote, contractor-centric company. Own end-to-end recruiting (sourcing, interviews, test projects, employer brand, metrics) and build scalable people systems (onboarding, performance frameworks, org design, contractor compliance) to support growth toward $100M. Partner with leadership and manage one direct report.

Lead and scale DTC ecommerce on Shopify and TikTok Shop to $20M+ revenue. Own P&Ls, paid media, creative testing, CRO, bundles/upsells, and lifecycle marketing (email/SMS). Build and manage a remote ecommerce team, launch monthly funnel offers, and meet ROAS, margin, and retention targets.