Top Tech Jobs & Startup Jobs in Chicago, IL

Develop graduate-level Applied AI course materials, including lessons, labs, case studies, assignments, rubrics, projects, readings, templates, and videos. Design practical activities using LLMs, RAG, AI agents, automation, APIs, and evaluation tools. Collaborate with learning designers and university faculty, explain complex concepts to nontechnical learners, maintain academic quality, and update content as AI tools and regulations evolve.

Conduct full-cycle consultative sales for advanced technical education programs targeting experienced technology professionals. Qualify prospects, discuss systems engineering, cloud, distributed systems, security, and AI concepts, tailor value propositions, close high-ticket deals, meet quotas, collaborate with sales and marketing leadership, and maintain pipeline documentation in HubSpot.

Own the full B2C sales cycle, from qualifying leads through closing and collecting payment. Present TripleTen’s value proposition, manage customer relationships, meet sales quotas, document lead activity in HubSpot, and collaborate with sales and marketing teams to improve pipeline performance. The role requires strong rapport-building, business acumen, accountability, teamwork, and a passion for helping customers advance their careers.

Own full enterprise sales cycle across Europe for B2B upskilling solutions. Lead complex, multi-stakeholder deals, build GTM and scalable playbooks, partner with BD, Product and Delivery, and drive new business and expansion in a pre-product-market-fit environment.

Teach and mentor experienced engineers transitioning to system architecture roles. Lead live sessions, office hours, and architecture review boards; review and assess student projects; provide written and verbal architectural feedback; run mock interviews; record instructional videos; and act as technical escalation for supporting instructors. Estimated 15–25 hours/week, async-first with scheduled US-timed live sessions.