Top Tech Jobs & Startup Jobs in Chicago, IL

Conduct outbound prospecting through calls, emails, and social media; research target accounts; qualify leads; schedule meetings for Account Executives; maintain CRM records; nurture prospects; collaborate with marketing; and report outreach progress against targets.

Own the full mid-market B2B sales cycle, including prospecting, discovery, demos, solution alignment, negotiation, and closing. Build and manage self-sourced and SDR-supported pipelines, acquire new customers, track sales performance, and collaborate with SDR, Customer Success, and Technical Support teams. Manage deals typically under $50,000 ACV while nurturing mid-sized client relationships and identifying business needs.

Own ambiguous, cross-team product engineering problems from framing through launch and iteration. Partner with product, design, and data; lead architecture, reliability, performance, and technical decisions across the stack. Influence teams without formal authority, mentor engineers, improve engineering practices, use metrics and experimentation, and apply AI throughout software development. Participate in on-call support.

Set technical direction for distributed messaging systems handling billions of messages daily. Make architecture decisions balancing scale, cost, and reliability; solve ambiguous cross-team problems; establish engineering standards; mentor senior engineers; improve processes and tooling; assess candidates; and use AI agents for multi-file software changes.

Provides tier 1–2 IT support across hardware, software, SaaS applications, and remote connectivity. Manages employee onboarding, offboarding, access changes, identity and access management, SSO, role-based permissions, and MDM device compliance. Supports endpoint protection, patching, documentation, and SOC 2, ISO, and HIPAA compliance activities. Collaborates with People, Security, and Engineering teams in a fully remote SaaS environment.

Manage accounts payable and travel-and-expense operations during a six-month contract. Responsibilities include reviewing and coding expenses, reconciling Ramp and Navan activity to the general ledger, enforcing policy, reviewing bills, identifying duplicate invoices, resolving vendor payment issues, and improving recurring processes. The role requires strong attention to detail, communication skills, and the ability to manage deadline-driven workloads.

Lead and develop a new team of eight mid-market Account Executives. Responsibilities include coaching, pipeline inspection, forecast accuracy, outbound generation, deal strategy, quota attainment, CRM hygiene, and cross-functional collaboration with Sales Operations, Marketing, and Solutions Architecture. The manager will establish team structure, improve execution, operationalize go-to-market initiatives, and maintain high performance standards in a remote SaaS environment.

Lead the global accounting function and team of approximately seven, overseeing close, general ledger, AP/AR, payroll, treasury, revenue recognition, equity compensation, controls, audits, tax coordination, and international compliance. Improve close timelines and reconciliation quality, author technical accounting memos, maintain audit-ready books, and drive automation across NetSuite and connected finance systems. Partner with senior stakeholders across the company while scaling accounting operations for a remote-first, multi-currency subscription business.

Lead company-wide product design vision, evolve the Pluma design system, and improve the connection between design intent and shipped products. Design experiences for developer and builder audiences, including CLI-native and API-first workflows, and lead human-AI and agentic product design. Partner with product and engineering leadership, guide design reviews, mentor Staff designers, raise organizational craft standards, and support hiring and calibration.

Own full-cycle recruiting for hard-to-fill go-to-market roles, with a strong emphasis on targeted outbound sourcing and engaging passive candidates. Build candidate lists, develop search strategies, partner with hiring managers, calibrate profiles using market data, manage candidate experience, and close offers. The recruiter will support Sales, Customer Experience, Marketing, and Business Operations searches, use AI tools to improve sourcing efficiency, and independently manage searches end to end.