Senior AI Enablement Engineer

Senior AI Enablement EngineerRemote (US) Full-time~8 days/month travel $175K – $250K OTE ABOUT OUTPOSTOutpost partners with leading AI companies to bring their products to enterprise customers. We embed with Fortune 1-500 companies to help them adopt AI tools and integrate agentic workflows into their day-to-day work. ABOUT THE ROLEAs a Senior AI Enablement Engineer, you'll work directly with enterprise engineering teams to help them get real value from cutting-edge AI products. You'll lead workshops, pair-program with engineers, consult on high-impact use cases, and guide teams through onboarding and adoption. This is a hands-on, people-first role. You'll be teaching, coaching, and building alongside customers—helping them see what's possible and giving them the skills to get there on their own. You'll also contribute to how we scale. Our enablement playbook is working well, and you'll help us refine and improve it based on what you learn in the field. IN THIS ROLE, YOU WILL • Lead interactive workshops and pair-programming sessions with enterprise engineering teams • Guide customers through installation, configuration, and optimization of AI tools • Identify high-ROI workflows and use cases across engineering, QA, data, and product teams • Create and refine enablement materials, best practices, and playbooks based on customer learnings • Collaborate with internal teams to continuously improve the onboarding experience • Travel to customer sites approximately 8 days per month REQUIREMENTS • 3–8+ years of experience as a software engineer or technical consultant • Strong backend engineering background (5+ years preferred) • Proven ability to communicate complex technical topics to diverse audiences • High empathy and a genuine orientation toward helping others succeed • Comfortable in ambiguous, fast-moving environments • Excellent verbal and written communication skills • Authorized to work in the United States YOU MIGHT EXCEL IF YOU • Have led technical workshops, enablement programs, or developer onboarding initiatives • Have deployed or integrated LLM or agent-based systems in production • Are energized by teaching and coaching—and by helping others reach 'aha' moments • Have worked at early-stage or high-growth companies where adaptability was essential