Top Tech Jobs & Startup Jobs in Chicago, IL

Provide frontline technical support via live chat (and phone/email as needed) for a property-management SaaS. Troubleshoot integrations (Airbnb, VRBO, Booking.com), calendar syncing, smart device connectivity, and AI features. Document issues in CRM, escalate bugs, maintain quality standards, and adapt communication style for diverse customers while working weekend/graveyard shifts.

Provide frontline technical support via live chat (plus phone/email) for a property-management SaaS: troubleshoot integrations, calendar syncing, smart devices, guide setup of AI replies and pricing, document issues in CRM, escalate bugs, and maintain quality and tone across diverse customers.

Manage end-to-end Amazon listing creation and health, map variations and attributes, prevent/resolves suppressions, sync inventory with Finale, translate listings to Walmart/Michaels, support Shopify and ShipStation handoffs, create SOPs, track listing metrics, and collaborate with a distributed team to rapidly list time-sensitive fabric collections.

Manage end-to-end interview scheduling and candidate communications, administer and configure Ashby ATS (templates, interview plans, pools), maintain data hygiene, deliver reporting and analytics, streamline recruiting operations, and partner with recruiters and hiring managers to improve scheduling SLAs and candidate experience.

Part-time freelance role creating and editing short-form video and audio, managing social channels and content calendars, executing outreach and lead generation, and auditing/optimizing HubSpot email campaigns and automations to drive demos and sales.

Manage and grow a global user community (primarily Discord): moderate discussions, respond to questions, triage technical issues, surface feedback to teams, support events and meetups, create repeatable processes, and improve tooling and workflows to drive engagement and community health.

Own the full inbound sales cycle for SMB/Mid‑Market clients: run frequent discovery calls with execs, qualify and close deals, manage pipeline in HubSpot, coordinate onboarding, and continuously improve through feedback and collaboration to hit quota.

Freelance YouTube and SEO specialist to repurpose Instagram content into search-optimized YouTube videos and LinkedIn posts. Own YouTube SEO, thumbnails, captions, upload schedules, community management, ManyChat DM automation, and content calendars. Support blog writing, creative ideation, analytics-driven optimization, and social media operations. Full-time remote (40 hrs/week, Eastern Time) with required home-office hardware and reliability.

Freelance remote specialist to design, implement, and manage a ClickUp workspace and provide executive-level operations support across two businesses. Responsibilities include ClickUp architecture, calendar and inbox ownership, drafting communications, preparing meeting materials, translating strategy into task plans, documenting SOPs, and driving adoption and continuous improvement to protect and optimize the executive's time.

Provide end-to-end US payroll processing (Paylocity), manage provider schedules in Athena, coordinate recruiting and interviews, deliver high-level executive EA support (calendar, inbox, meetings, travel/expenses), run team offsites and events, maintain SOPs, and recommend process improvements to ensure operational continuity.