Top Tech Jobs & Startup Jobs in Chicago, IL

Build outbound and inbound sales pipelines, manage high-volume SMB opportunities, conduct product demos, advise HR teams, close new business, achieve quota, and provide customer feedback. The role requires selling HR technology or B2B SaaS, maintaining accurate pipeline data, using modern sales tools, and partnering with implementation teams for customer handoffs.

The Controller will own monthly close, financial reporting, reconciliations, revenue recognition, order-to-cash, internal controls, and audit readiness. They will build accounting policies and infrastructure, select and implement ERP and billing systems, adopt AI finance tools, oversee outsourced accounting, and eventually hire and lead an internal accounting team. The role requires strong US GAAP and ASC 606 expertise, systems fluency, startup-building ability, and 8 to 10+ years of relevant experience.

Own customer account growth, renewals, expansion, adoption, retention, referrals, and customer experience. Develop lifecycle engagement programs, analyze customer data, lead strategic business reviews, resolve escalated issues, and identify expansion opportunities. Partner with Sales as a subject matter expert and solutions architect while coordinating cross-functional resources to improve customer outcomes and revenue performance.

Own full-cycle recruiting across sales, marketing, customer experience, revenue operations, partnerships, engineering, and product. Partner with hiring managers, source and engage candidates, build talent pipelines, manage interview processes, deliver strong candidate experiences, analyze recruiting metrics, and support talent strategy in a high-growth startup environment.

Own Sparrow’s product marketing strategy, including positioning, messaging, website copy, product and feature launches, market and buyer research, win/loss analysis, ideal customer profile refinement, and competitive intelligence. Partner cross-functionally with Marketing, Product, Revenue Enablement, Sales, and Account Management to support growth and develop sales training and enablement materials for a B2B SaaS product.

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.

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.

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.

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 and scale Sparrow's GTM partnerships with HRIS, disability carriers, payroll systems, PEOs, and point solutions. Secure and deepen partnerships, drive partner-sourced pipeline and closed-won revenue, coordinate cross-functional teams for integrations and shared customers, develop joint GTM initiatives, and build scalable processes, playbooks, and enablement for partner success.