Senior AI Engineer
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Worldwide
Semi-flexible schedule
Fully-remote
full-time (40 hrs/week)
Long-term role

Senior AI Engineer   $200,000 USD/year

Description

You're a full-stack product engineer seeking ownership rather than task lists. This role places you in command of an AI product from start to finish: engaging with customers on a weekly basis, deciding what features to develop, and deploying to production. You have two core objectives: enabling Kayako One to resolve support tickets autonomously without human intervention, and constructing an AI-powered sales pipeline that guides prospects from initial contact through deal closure. You determine the technology stack, product roadmap, release schedule, and final results.

Much of the software industry isolates engineers from end users under the guise of "process." That's not our approach. No chain of product manager → designer → "customer success" stands between you and ground truth. You will conduct weekly discovery sessions, convert user pain into product requirements, ship rapidly, and track tangible outcomes. You'll also build the AI sales automation infrastructure that may serve as the blueprint for Trilogy's portfolio-wide sales strategy. Here, adoption metrics, resolution rates, customer satisfaction scores, and pipeline velocity define success.

This position means owning the entire product: developing new AI capabilities in Kayako One that improve ticket resolution performance; building integrations with CRM and ticketing systems; designing outreach workflows and targeting algorithms; creating pipeline connectors; producing reports that validate effectiveness; and managing deployments, system monitoring, and incident handling to maintain uptime. This is not a backend-only role executing tickets specified by others, nor a comfortable lane with structured handoffs. You'll write code when necessary, configure AWS infrastructure expertly, adopt tools such as Voiceflow or Cursor without hesitation, and ensure LLMs perform reliably in production rather than merely impressing in demos.

You'll operate at the leading edge of our help desk solution and an AI sales automation initiative, with visibility across the portfolio. Success means customers actively use your releases, resolutions happen faster, end users report higher satisfaction, and the pipeline moves more cleanly and quickly. If you want to own results, engage with customers weekly, filter out distractions, and ship what actually moves the metric, this opportunity is for you.

What you will be doing

  • Develop and deploy Kayako One capabilities—AI that increases ticket resolution, integrations with CRM/ticketing platforms, robust and scalable infrastructure, plus performance optimizations and bug resolutions.
  • Conduct weekly discovery sessions with customers to convert actual pain points into product requirements and confirm direction with real users.
  • Construct the AI sales automation infrastructure—outreach workflows, integrations with pipeline and sales tools, automated progression through sales stages, and reporting on performance metrics.
  • Take full ownership of deployment and operations—end-to-end releases, monitoring/alerting/incident management, and AWS/database architecture.

What you will NOT be doing

  • It isn't simply coding to specifications provided by someone else — you're defining what gets built based on customer feedback.
  • It isn't work confined to staging environments — everything you create reaches production and actual customers.
  • It isn't narrow technical specialization — you control the complete stack, infrastructure, and customer-facing experience.

Key responsibilities

  • Develop and maintain an AI-driven customer support system that resolves tickets without requiring human agents
  • Develop and maintain a complete AI sales pipeline that manages deals from initial contact through closure

Candidate requirements

  • At least 5 years of professional software development experience
  • Experience owning entire products or major systems, not just features
  • Experience shipping AI/LLM-powered products to production (not just prototypes or demos)
  • Deep AWS experience, including Lambda, S3, OpenSearch, RDS, CloudWatch, EventBridge, EC2, Route 53, CloudFront
  • LLM/AI integration experience, including Claude/ChatGPT prompt engineering, API integration
  • Experience coding in Python, Java, and JavaScript
  • Experience using MySQL database
  • Experience using Docker, deployment pipelines, and GitHub workflows
  • Experience with OpenAI and JWT API development
  • Experience with DNS management and web infrastructure
  • Customer-facing experience

Meet a successful candidate

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Fabiano Lucchese
Fabiano  |  SVP of Software Engineering
Brazil  

Does your company encourage your natural creativity? This Brazilian engineering leader rediscovered his purpose after unleashing both his an...

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