Top Tech Jobs & Startup Jobs in Chicago, IL

Prepare customized payroll plans and reconciliations for customers, support leave specialists with accurate payroll calculations, collaborate with payroll teams and internal stakeholders, collect product feedback, and identify improvements to payroll calculation software and integrations.

Support planning and execution of in-person and virtual B2B events (webinars, dinners, tradeshows). Manage logistics, vendors, assets, budgets, promotions, attendee data, and post-event reporting in partnership with marketing, sales, and partnerships teams.

Lead development and execution of strategic partner programs and go-to-market for brokers, consultants, and channel partners. Build and manage high-value relationships, create enablement resources and training, identify new growth partnerships, collaborate cross-functionally on product and market strategies, and track performance metrics to drive partner adoption and shared revenue goals.

Lead HRIS and SSO integration setup, testing, and troubleshooting for new and existing customers. Configure integrations with major HRIS platforms, validate data flows, support onboarding calls and dashboard demos, document processes, and collaborate with engineering, CX, and sales to resolve issues and improve integration workflows.

Manage existing customer relationships to drive adoption, retention, renewals, upsells, and referrals. Own revenue targets, run QBRs, resolve escalations, identify expansion opportunities, and use customer data to improve engagement and reduce churn. Partner cross-functionally and support sales as a solutions expert.

Lead and build Sparrows revenue operations function across the customer lifecycle. Own forecasting, reporting, analytics, pricing, quota setting, deal desk, commissions, and sales tech stack automation. Partner cross-functionally with Sales, Product, Account Management, Customer Experience, and Marketing to drive revenue growth, retention, and operational efficiencies tied to OKRs and KPIs.

Manage end-to-end employee leaves for US and Canada across multiple companies, ensuring compliance with FMLA/ADA and company policies. Communicate with employees, HR, payroll, and third parties; maintain confidential records; partner on payroll and claims; track metrics and SLAs; provide customer service, product feedback, and process improvements.

Lead GTM and revenue enablement: define messaging and differentiation, create sales enablement content (decks, battle cards, case studies), drive product launches, measure and improve sales productivity, implement sales tech stack, and run onboarding, training, and communications to support Sales and Customer Success.

Manage and process employee leave paperwork and correspondence, coordinate with external administrative contacts, document escalations, maintain internal systems, and support continuous process improvements in a fast-paced, remote environment.