Top Tech Jobs & Startup Jobs in Chicago, IL

Leads and scales Packback’s enterprise and higher-education sales organization. Owns revenue strategy, go-to-market motions, organizational design, staffing, compensation, forecasting, pipeline management, and board-level reporting. Manages and coaches sales managers and Account Executives, drives complex multi-stakeholder deals, recruits talent, and improves team performance. Partners with Marketing, Product, Customer Success, Revenue Operations, Finance, and the CEO to align strategy and expand institutional adoption. Requires domestic travel for campus visits, conferences, and executive meetings.

Application for the 2026 Progressive Talent Pipeline endorsement cohort. Applicants must submit a resume, brief biography, required short-answer responses, and essays addressing government interest, policy priorities, elected officials, and the Biden administration. The program supports individuals interested in future roles in Congress, federal agencies, and state or local government. Applications are reviewed on a rolling basis through October 25, 2026.

Partner with Head of Finance & Strategy to lead cross-functional, high-priority initiatives. Build reporting rhythms, financial models, dashboards, processes, and AI-driven automations. Support board and investor reporting, drive execution across finance, GTM, ops, and product analytics, and create structure in ambiguous areas at a high-growth, remote-first insurtech.

Supports financial operations through project setup, profitability monitoring, reconciliations, variance analysis, cash flow modeling, accounts payable, accounts receivable, invoicing, collections, state tax compliance, DCAA compliance, and audit preparation. Partners with project managers, internal finance staff, and outsourced accounting providers while responding to financial process questions and maintaining accurate documentation.

Drive new business sales for TCP’s workforce management SaaS solutions across State, Local Government, and Education accounts. Responsibilities include territory planning, prospecting, consultative selling, managing RFPs and procurement processes, conducting demonstrations, forecasting opportunities, maintaining CRM records, achieving revenue quotas, and developing customer relationships throughout the full sales cycle. The role requires at least 3 years of SaaS sales experience and involves 20–30% travel.

Leads enterprise commercial sales to employers with 1,000+ employees, owning territory strategy, pipeline development, broker and benefits-consultant partnerships, consultative discovery, complex 12+ month sales cycles, forecasting, and contract closure. The role targets healthcare and benefits decision-makers, develops ROI-based business cases, coordinates cross-functional deal execution, and supports successful client launches. Approximately 50% travel is required, along with U.S. work authorization.

Creates graphics and layouts for digital and print media, including brochures, flyers, and social media content. Collaborates with marketing to produce brand-aligned materials, contributes creative ideas, maintains visual consistency, and manages multiple projects while meeting deadlines.

Owns NetSuite administration, functional architecture, configuration, integrations, data integrity, UAT, and post-go-live optimization. Partners with implementation consultants and finance leaders to support an enterprise ERP transformation, including migration from Microsoft Dynamics. Configures financial modules, workflows, approval routing, reporting, roles, permissions, and multi-entity processes while ensuring alignment with US GAAP and internal controls.

The Founding Sales Development Representative will build Sprinto’s outbound enterprise sales engine across North America. Responsibilities include high-volume cold calling, account planning, multithreaded engagement across buying committees, creating urgency, qualifying opportunities into Sales Accepted Leads, and partnering with Account Executives to drive pipeline and quota attainment. The role requires measurable outbound sales performance, strong phone skills, commercial curiosity, and continuous improvement through coaching and metrics.

The Senior Managing Director will lead and oversee curriculum design and instructional materials development, managing projects and client relationships while ensuring high-quality standards and alignment with educational frameworks.