Top Tech Jobs & Startup Jobs in Chicago, IL

Own the customer-facing Superhuman experience and Console, including live conversations, builder tools, self-serve activation, analytics, personalization, and weekly releases. Partner with design, engineering, and leadership to improve time-to-value, retention, and customer outcomes. Lead product decisions across web, voice, and video experiences while enabling customers to create, tune, test, and measure AI-powered revenue teammates independently.

Own the agent runtime and orchestration platform powering AI-driven go-to-market Superhumans. Define planning, tool calling, memory, guardrails, multi-agent handoffs, packaged workflows, evaluation harnesses, APIs, and enterprise configuration. Partner with GenAI and engineering teams to ship weekly, prototype solutions, write technical specifications, and measure agent performance through task success, escalation precision, hallucination, and tool-error metrics.

Design and optimize AI conversation systems, including specialized subagents, routing and delegation workflows, prompt strategies, context management, and structured agent contracts. Diagnose conversational issues through transcript analysis, build prototypes using APIs and light coding, develop RAG and fine-tuning workflows, and create multimodal prompting strategies. Train colleagues and AI agents while documenting practices and leading initiatives in conversational AI.

Own a portfolio of B2B SaaS customers from onboarding through renewal and expansion. Drive adoption, value realization, and measurable outcomes; define success criteria; advise revenue, marketing, and operations stakeholders; lead business reviews, renewals, and expansion opportunities; and share customer insights to influence product direction and scalable success playbooks.

Enterprise Account Executive responsible for full sales cycle from outbound to close and expansion. Build pipeline, lead executive-level discovery and demos, evangelize AI-led GTM, partner with GTM leadership, and travel ~30% for in-market sales. Expected to consistently exceed quota and operate with ownership, process discipline, and executive presence.

Own GTM enablement programs spanning new-hire onboarding, ongoing training, customer education, content development, and strategic initiatives. Partner with Sales, Customer Success, RevOps, Product, and Marketing to improve ramp time, productivity, certification, adoption, and revenue impact. Deliver live and asynchronous training, use AI to enhance enablement, manage content and knowledge resources, and measure program effectiveness in a fast-changing B2B SaaS environment.

Designs prompts, context-management strategies, subagent architectures, routing systems, and agentic workflows for conversational LLMs. Builds prototypes using APIs, RAG, fine-tuning, and multimodal prompting; reviews agent conversations and feedback to improve performance. Documents processes, trains colleagues, and becomes the internal expert on the dialogue platform and prompting practices.

Run full enterprise sales cycle from outbound to close and expansion. Build pipeline from scratch, lead executive-level discovery and demos, evangelize AI-led GTM, partner with GTM leadership, and consistently exceed quota through strategic, data-driven execution and strong executive presence.

The Account Executive will handle the full sales cycle for mid-market and enterprise clients, focusing on executive outreach and AI-led revenue growth, while building pipeline and managing strategic demos.