AI Software 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 full-stack product engineer seeking ownership over task lists. This role puts you in command of an AI product from end to end: weekly customer meetings, deciding what ships, and deploying to production. Your dual objectives: drive Kayako One to resolve support tickets autonomously and construct an AI sales pipeline that moves prospects from initial contact through deal closure. You own the technology stack, product roadmap, release schedule, and final results.

The broader industry isolates engineers from end users under the banner of "process." We take a different approach. No chain of PM → designer → "customer success" stands between you and the ground truth. You'll lead weekly discovery sessions, convert user pain into product decisions, ship quickly, and track tangible outcomes. You'll also architect the AI sales automation stack that may serve as the blueprint for Trilogy's portfolio-wide go-to-market motion. Here, adoption metrics, resolution rates, CSAT scores, and pipeline velocity define success.

This position means owning the complete system: new AI capabilities in Kayako One that improve ticket resolution performance; integrations spanning CRMs and ticketing systems; outreach workflows and targeting rules; pipeline connectors; reporting that validates impact; plus deployments, monitoring, and incident management to maintain uptime. This is not a backend-focused role executing pre-defined tickets, nor a comfortable lane with handoffs. You'll write code when required, configure AWS infrastructure expertly, adopt tools like Voiceflow or Cursor without friction, and ensure LLMs deliver in production rather than merely impress in demos.

You'll operate at the leading edge of our help desk product and an AI sales automation initiative, with exposure across the portfolio. Success means customers actively use your work, resolutions accelerate, end users report higher satisfaction, and the pipeline moves cleaner and faster. If you want to own results, engage customers weekly, filter out distractions, and ship what truly shifts the metrics, this role is for you.

What you will be doing

  • Design and deliver Kayako One features—AI capabilities that improve ticket resolution, integrations with CRM and ticketing platforms, robust and scalable infrastructure, plus performance enhancements and bug remediation.
  • Lead weekly customer discovery sessions to convert user pain into actionable requirements and validate product strategy with real users.
  • Construct the AI sales automation stack—outreach sequences, integrations with pipeline tools, automated progression through sales stages, and dashboards that track performance.
  • Take full ownership of deployments and operations—end-to-end releases, monitoring/alerting/incident handling, and management of AWS and database infrastructure.

What you will NOT be doing

  • This isn't simply coding against a specification someone else wrote — you define what gets built based on customer feedback.
  • This isn't work that remains in staging environments — every feature you create reaches production and actual customers.
  • This isn't narrow technical specialization — you control the entire stack, infrastructure layer, and user experience.

Key responsibilities

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

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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