Top Tech Jobs & Startup Jobs in Chicago, IL

Leads marketing and go-to-market strategy for the Flooring business unit, owning market positioning, buyer personas, competitive intelligence, product launches, sales enablement, demand generation, and customer expansion. Partners with the Flooring GM, Product Management, Sales, and Revenue Marketing to drive bookings and commercial outcomes. Manages a small team using a player-coach approach in a high-growth, PE-backed SaaS environment.

Own the entire post-sale client lifecycle: onboard customers, review AI-generated compliance documents, deliver updates from regulatory monitoring, run upsell campaigns, retain and expand accounts, and feed product feedback to the founder. Build processes and define client success at an early-stage SaaS startup.

Prospect, pitch, and close new media advertising business while growing existing client accounts. Sell digital, video, branded content, OTT/CTV, and sponsorship solutions to brands and agencies. Manage pipeline and sales activity in Salesforce and Gong, represent Outside at industry events, build client relationships, and collaborate with internal teams to deliver campaigns. The role requires media sales experience, strong prospecting and presentation skills, NYC-area residency, and familiarity with outdoor, fitness, or active lifestyle markets.

Own the AI product roadmap, prioritization, accuracy metrics, model and vendor requirements, release planning, and correction feedback loop. Partner with engineering, product, tax, QA, UX, and client success to improve document extraction coverage, accuracy, cost, latency, and filing readiness across K1x products.

Design, build, and launch AI-focused software capabilities using Python and distributed-systems principles. Own initiatives from solutioning and architecture through production implementation and launch while remaining hands-on with code. Collaborate with Nextiva engineering and product teams, Google Gemini, and other external technology partners to extend AI capabilities across partner environments and the Nextiva ecosystem. Solve ambiguous early-stage technical problems and contribute to system design and architecture decisions.

Build and manage 7AI’s regional partner ecosystem across the Mid-Atlantic and Great Lakes. Own partner-sourced and partner-influenced revenue targets, run co-sell motions with resellers, SIs, MSSPs, technology alliances, and cloud partners, and develop repeatable channel revenue through account mapping, joint business planning, and pipeline reviews. Collaborate with sales, marketing, product, and executives to strengthen partner value propositions and expand regional market opportunities.

Provides Level 2 application support for enterprise financial and business applications. Responsibilities include incident resolution, root cause analysis, batch and interface monitoring, system health checks, change and release validation, UAT support, ticket management, reporting, and collaboration with development, infrastructure, vendors, and L3 teams. The role requires Java knowledge, SQL, Unix command-line skills, monitoring and scheduling tools, and availability for onsite 24x7 rotational shifts.

Supports esports trading operations by entering player and game statistics, grading projections, settling games, and monitoring real-time markets for accurate payouts. The role includes posting and pricing markets across esports titles and requires night and weekend availability. WOOF WOOF

Leads scalable data model and pipeline design, dbt development, testing, CI/CD, and analytics engineering implementations. Partners with analysts, engineers, and stakeholders to translate business needs into reliable models and semantic layers. Advises on data architecture, governance, quality, performance, and long-term scalability while mentoring peers and contributing to shared tooling, standards, and frameworks.

Lead client discovery and executive engagement to identify high-value AI and data opportunities. Translate ambiguous business problems into use cases, hypotheses, MVP scopes, business cases, and measurable KPIs. Facilitate workshops, prototype solutions using AI-assisted and low/no-code tools, and partner with technical teams to develop scalable solutions. Manage client alignment, scope, risk, adoption, and change communication while connecting technology investments to business value.