HeyMilo AI

Technical Customer Success Manager – AI Tuning

HeyMilo AI

full-time

Posted on:

Location Type: Hybrid

Location: TorontoCanada

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About the role

  • Work closely with customers and customer success to define and track success metrics
  • Monitor performance of deployed AI agents and identify gaps
  • Tune prompts, workflows, and agent behavior to improve outcomes
  • Iterate on agent logic, tool usage, and context management
  • Debug issues across prompts, integrations, and system behavior
  • Translate real-world usage into product and system improvements

Requirements

  • Strong technical background with ability to code when needed
  • Deep experience with prompt engineering and LLM behavior
  • Strong understanding of agent systems (tool calling, context management, orchestration)
  • Heavy user of AI tools (Cursor, Claude, Codex, etc.)
  • Ability to debug ambiguous issues across AI and system layers
  • Strong ownership and communication skills
  • Comfortable working under pressure and tight timelines
  • Able to own outcomes, not just tasks
  • Experience implementing agentic workflows or AI agents in enterprise environments
  • Programming fundamentals + Python/JS experience are a huge plus
Benefits
  • Direct ownership over how AI performs in the real world
  • Work on high-impact problems tied to customer outcomes
  • High visibility across product, engineering, and customer teams
  • Fast-paced, execution-driven environment
Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills & Tools
prompt engineeringLLM behavioragent systemstool callingcontext managementorchestrationdebuggingPythonJavaScriptprogramming fundamentals
Soft Skills
communication skillsownershipworking under pressuretime management