Top Tech Jobs & Startup Jobs in Chicago, IL

Develop and support customer integrations by designing workflows across the core product and external platforms such as QuickBooks, Salesforce, and NetSuite. Translate customer requirements into complete solutions, deliver projects on schedule, maintain project documentation, resolve technical challenges, communicate roadblocks, and mentor team members. The role requires API experience across multiple products, scripting expertise, strong communication, adaptability, and attention to detail.

Leads technical implementations and integrations for higher education partners, owning workstreams from discovery through go-live. Configures SIS integrations, maps and validates data, troubleshoots system issues using SQL, logs, and datasets, and manages integration risks. Serves as the primary technical partner contact, translates complex issues for varied audiences, collaborates with Product and Engineering, and develops scalable documentation, runbooks, and implementation processes.

Own an enterprise territory and full sales cycle, prospecting and closing new logos while growing named accounts. Generate outbound pipeline through Apollo and HubSpot, manage forecasting, sell language technology and platform offerings, and collaborate with presales, SDR, partnerships, and account teams. Build enterprise relationships, structure complex deals, provide market intelligence, and consistently meet or exceed quota.

Provides first-level analysis, triage, troubleshooting, monitoring, and resolution for customer incidents and technical requests. Communicates proactively with customers, documents issues and resolutions, escalates to Level 2 support when needed, collaborates with vendors, and follows ITIL practices. The role requires familiarity with operating systems, servers, virtualization, Linux, networking, firewalls, and command-line tools. It includes a three-month training period and may involve day or overnight shifts.

Sell TeamDynamix SaaS solutions to enterprise organizations across corporate, higher education, healthcare, and government sectors. Responsibilities include generating net-new business, developing executive relationships, conducting discovery, managing complex sales cycles, partnering with sales development and pre-sales engineering teams, delivering presentations, negotiating contracts, forecasting, and meeting sales objectives. The role is remote, supports multiple Northern Plains states, and requires travel for prospect engagements and industry events.

Own the full enterprise sales cycle for HyperSphere’s keyless data protection solution. Responsibilities include cold prospecting, pipeline creation, value-based discovery, enterprise presentations, negotiations, closing $50K–$250K ARR deals, and navigating procurement, legal, and security reviews. The role partners with Sales Engineering on demos and Proofs of Value while engaging CISOs and security architects across multiple industries.

Join a research and advisory pipeline for an asset-management startup building an auditable reasoning engine. Advise on agentic AI, world models, interpretability, and systemic risk. Help shape research direction, identify failure modes and guardrails, and provide scholarly evidence (papers, GitHub, Google Scholar) and a short written response to demonstrate expertise.

Leads Checkmate’s global post-sale operations organization across onboarding, menu management, and technical account management. Owns service strategy, customer satisfaction, operational metrics, enterprise escalations, onboarding outcomes, process standardization, and team performance. Partners with Sales, Product, and Engineering to resolve systemic issues, improve product capabilities, reduce churn, and scale workflows through automation and AI-driven analytics. Acts as a strategic operational partner to the CEO.

Manage enterprise customer accounts throughout deployment, adoption, value realization, and renewal. Build success plans, monitor customer health and KPIs, conduct executive business reviews, resolve escalations, and drive retention, satisfaction, cross-sell, and upsell opportunities. Partner with Sales, Support, Product, Renewals, and Professional Services while identifying risks, coordinating issue resolution, and improving scalable customer success processes.

Own full-cycle enterprise sales across Fortune 500 accounts, from prospecting and executive discovery through negotiation and multimillion-dollar contract close. Build pipeline, develop account and territory plans, lead complex MEDDPICC sales cycles, present AI-driven business cases, and coordinate solution consultants, partners, customer success, and marketing. Co-sell with Microsoft, AWS, systems integrators, and consulting firms while securing net-new logos and transitioning customers for expansion.