Apply on Kit Job: kitjob.ca/job/2g8s2x

Overview

HeyMilo is building AI interviewers that run real conversations with candidates. We help companies screen faster and make better hiring decisions using conversational AI. We work closely with customers to deploy AI into real hiring workflows and ensure it delivers measurable outcomes.

The Role

We’re hiring a Forward Deployed AI Engineer to own the performance and success of AI agents in production. This role sits at the intersection of engineering, product, and customer success. You’ll work directly with customers post-deployment to ensure their AI agents are performing at a high level and continuously improving.

What You’ll Do

- 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

What We’re Looking For

- Solid 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

Bonus

- Experience with conversational AI across voice, SMS, or chatbots
- Experience with telephony or voice systems
- Experience evaluating and improving production AI systems
- Familiarity with recruiting, HR tech, or workflow automation

Why join

- 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

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Apply on Kit Job: kitjob.ca/job/2g8s2x

📌 Technical Customer Success Manager (AI Tuning) (Toronto)
🏢 HeyMilo AI
📍 Toronto