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 

Not accepting applications on crossover.com at this time.

Description

You're a product-focused engineer seeking ownership over execution tickets. This position places you in command of an AI product from end to end: weekly customer meetings, feature prioritization, and production deployments. Two core objectives define the role: drive Kayako One to resolve support tickets autonomously and construct an AI-driven sales pipeline that guides prospects from initial contact through deal closure. You determine the technology choices, development priorities, release timing, and business results.

The broader industry segregates engineers from end users under the guise of "process." Our approach is different. No intermediary layer of PM → design → "customer success" stands between you and market reality. You'll conduct weekly discovery sessions, convert user pain into working product, deliver rapidly, and track tangible outcomes. You'll also architect the AI sales automation infrastructure that may serve as the blueprint for Trilogy's portfolio-wide go-to-market motion. Success metrics here are adoption rates, resolution performance, CSAT scores, and pipeline velocity.

This position means full ownership: new AI capabilities in Kayako One that elevate ticket resolution performance; connections to CRMs and ticketing systems; outreach sequences and targeting algorithms; pipeline integration points; analytics proving effectiveness; plus deployments, system monitoring, and incident management to maintain uptime. This is not a backend-only role executing pre-defined specifications, nor a comfortable lane with structured handoffs. You'll write code where necessary, configure AWS infrastructure expertly, adopt tools like Voiceflow or Cursor without friction, and ensure LLMs perform reliably in production rather than merely impressing in demos.

You'll operate at the sharp edge of our help desk product and an AI sales automation initiative, with visibility across the portfolio. Success manifests as customers actively using your releases, improved resolution speed, elevated end-user satisfaction, and a more efficient, accelerated pipeline. If you seek to own results, engage customers weekly, filter out distractions, and ship what actually moves key metrics, this opportunity is designed for you.

What you will be doing

  • Develop and deploy Kayako One capabilities—AI systems that improve ticket resolution, integrations with CRM/ticketing platforms, robust/scalable infrastructure, and performance/defect remediation.
  • Conduct weekly customer discovery sessions to convert actual pain points into product specifications and confirm product strategy with end users.
  • Develop the AI sales automation infrastructure—outreach sequences, pipeline/tool connectors, automated sales progression, and outcome analytics.
  • Manage deployments and operational health—end-to-end releases, monitoring/alerting/incident handling, and AWS/database architecture.

What you will NOT be doing

  • It isn't simply coding against a provided specification — you're determining what gets developed based on customer feedback.
  • It isn't work confined to staging environments — every feature you create reaches production and actual customers.
  • It isn't specialized in a single domain — you control the complete stack, infrastructure layer, and user experience.

Key responsibilities

  • Develop and maintain an AI-driven customer support system that resolves tickets without human intervention
  • Develop and maintain a complete AI sales pipeline that moves 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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