Top Tech Jobs & Startup Jobs in Chicago, IL

Design and develop realistic, research-driven simulation scenarios and materials for interpersonal skills practice. Conduct audience and context research, author participant and client-facing content, draft scoring criteria, consult with SMEs and clients, iterate with AI tools, train simulation facilitators, and use feedback and data to refine simulations for authenticity and learning impact.

Lead, hire, coach, and manage a team of net-new Account Executives in North America to acquire enterprise logos. Define target accounts, operationalize ABM, optimize outreach using Salesforce/Apollo/SignalHire/HubSpot, enforce CRM hygiene and forecasting, create playbooks, and drive adoption of MEDDPICC to meet and exceed booking targets.

Lead the creation of a global civic technology platform from concept to mass adoption. Translate complex, multi-stakeholder democratic challenges into a consumer product using AI, human input, and scalable engagement mechanisms. Own product vision, strategy, development, and global deployment while driving effective policy outcomes and cross-partisan civic participation across millions of users.

Own First Connect’s community strategy for independent insurance agents, including launching an online community, ambassador program, industry partnerships, events, webinars, content, and beta programs. Measure community health, engagement, pipeline contribution, retention, and NPS, presenting insights to leadership. Collaborate with Marketing, Product, Sales, Carrier, and Events teams while serving as a public-facing representative at industry gatherings. The role is fully remote in the United States and requires approximately 20–30% travel.

Leads and develops a team of Account Executives selling B2B SaaS solutions to corporate real estate occupiers. Responsibilities include achieving sales targets, executing sales strategy, recruiting and retaining talent, coaching team members, building executive relationships, forecasting opportunities, negotiating commercial terms, and collaborating with Marketing, Product, Professional Services, and Legal.

Leads accounting and finance operations across US and Canadian entities, overseeing reporting, treasury, audits, tax compliance, internal controls, finance systems, acquisitions, refinancing, and financial integration. The VP develops the finance team, drives process automation and technology adoption, prepares executive and board reporting, and advises leadership and private equity stakeholders on financial strategy and organizational growth.

Build and manage strategic partnerships across government agencies, associations, universities, nonprofits, consultants, resellers, and systems integrators. Develop go-to-market strategies, represent the company in external meetings and events, create partnership models, generate qualified opportunities, gather market insights, and build repeatable systems and playbooks. Collaborate with sales, product, deployments, marketing, and leadership to expand market presence and support growth.

Own the roadmap and execution for core pricing, risk, and AI platform foundations across the insurance policy lifecycle. Partner with customers, brokers, underwriters, engineering, data science, actuaries, and go-to-market teams to prioritize problems, shape product direction, make technical decisions, and deliver products on aggressive timelines. The role requires quantitative strength, strong communication, cross-functional leadership, and experience working in high-growth environments.

The Cybersecurity Engineer detects and responds to threats, improves endpoint visibility and security posture, supports incident response, automates alerting and reporting, manages vulnerabilities, and partners with IT on patching and system hardening. The role monitors hybrid environments, investigates suspicious activity, documents security standards, and drives continuous improvement. It requires enterprise IT and cybersecurity experience, endpoint security expertise, scripting skills, and strong Windows Server knowledge.

Manage a portfolio of high-value real-money gaming players, building relationships and delivering personalized communications, rewards, and experiences. Drive retention, reactivation, engagement, and player lifetime value through data-informed initiatives. Resolve VIP requests and escalations professionally, collaborate with Product and Marketing, provide player insights, and ensure responsible gaming and regulatory compliance. The role is fully remote, primarily aligned with US time zones, with occasional weekend availability required.