CareerPlan

Regional GM - Chicago (Remote)

East Coast, United StateRemoteFull-time2026-10-02 → 2026-11-11
Remote

Core

Lead go-to-market motion and land first major enterprise customers for an AI-first startup building LLM-powered applications.

Role type

Regional General Manager (Enterprise Sales)

Builds

LLM-powered applications for Fortune 500 enterprises

Domain

Enterprise AI / Large Language Models / Digital Transformation

Deliverable

production ML models

Required skills

Enterprise software sales, complex multi-stakeholder sales cycles, building pipeline from zero, translating AI/ML capabilities to business outcomes, architecting multi-year expansion strategies, selling to C-suite and CIOs

Preferred skills

Experience in FinServ, Healthcare, Manufacturing, or Retail, background in AI/ML platforms or management consulting, success in highly regulated industries

Technologies

LLMs, AI/ML platforms

Responsibilities

Lead complex sales cycles into regulated industries, build pipeline from zero for strategic enterprise accounts, translate technical AI capabilities into business outcomes, architect multi-year expansion strategies, collaborate with founders to refine enterprise strategy

Seniority

Senior, hands-on IC