Top Tech Jobs & Startup Jobs in Chicago, IL

Six-month unpaid, full-time apprenticeship to edit, repurpose, and publish a founder's daily B2B SaaS content across YouTube Shorts, X, Reddit, and Substack. Responsibilities include video editing (Descript), platform-native formatting, publishing with optimized metadata, monitoring engagement, and iterating to maximize reach. Exclusivity and regional eligibility required.

Six-month unpaid apprenticeship to manage pilot customers and inbound sales pipeline for an early-stage SaaS founder. Responsibilities include Slack concierge support, CRM pipeline triage, daily data QA, and creating Notion help docs and Loom tutorials. Heavy emphasis on written B2B communication, organization, and accurate CRM/data handling.

Six-month, unpaid intensive apprenticeship to build and maintain live no-code/low-code revenue data pipelines. Responsibilities include QA of intent data, building n8n workflows, writing basic JavaScript to transform payloads, and troubleshooting API calls and webhooks to ensure delivery to Slack, CRMs, and email tools.

Six-month, unpaid full-time apprenticeship operating AirOps AI workflows to convert CEO LinkedIn content into programmatic SEO/AEO assets. Execute bulk refreshes, generate metadata and optimized headers, push Markdown/JSON to Contentful or Sanity via GitHub, and upskill through AirOps Academy to build a portfolio for technical marketing roles.

Advise as an outbound Playbook Architect: design multi-channel, intent-driven outbound sequences, write copy frameworks and AI prompt logic, and deliver ready-to-launch playbooks that maximize replies and booked meetings. Work asynchronously as an equity-bearing advisor while keeping a full-time job.

Join as a Revenue Co-Founder to build GTM and pipeline architecture: run pilots, generate and close early revenue, own P&L, perform SDR/AE/CSM duties, and recruit a sales team to scale to $1M ARR.

Lead omnichannel demand generation to produce large volumes of first-party intent from SDR Leaders, RevOps, and Demand Gen. Use AI-first tools and programmatic channels (content, ads, events, SEO) to drive scored signals, measure incrementality, pilot the product, and collaborate with sales. Accept co-founder equity-first compensation; West Coast proximity preferred.