Technical Lead, Trilogy (Remote) - $200,000/year USD

You're a full-stack product engineer seeking ownership rather than task lists. This position gives you end-to-end responsibility for an AI product: direct weekly customer engagement, autonomous build decisions, and continuous production deployment. Your dual objectives: enable Kayako One to resolve support tickets autonomously and construct an AI-driven sales pipeline that moves prospects from initial contact through deal closure. You command the technology stack, feature roadmap, release schedule, and business results.

The broader industry isolates engineers from end users under the guise of "process." Our approach is different. No intermediary chain of PM → designer → "customer success" stands between you and ground truth. You'll conduct weekly discovery sessions, convert customer pain into product specifications, deploy rapidly, and track meaningful business metrics. You'll also architect the AI sales automation framework that may define Trilogy's go-to-market approach across its entire portfolio. Success here is measured by adoption metrics, resolution rates, CSAT scores, and pipeline velocity.

This role means owning the complete system: novel AI capabilities in Kayako One that improve ticket resolution performance; connectivity with CRM and ticketing systems; outreach automation and targeting algorithms; pipeline data connectors; analytics that validate efficacy; plus all deployment, system monitoring, and incident management required to maintain uptime. This is not a backend-only position executing pre-written specifications, nor a comfortable lane with structured handoffs. You'll write code when necessary, configure AWS infrastructure expertly, adopt tools like Voiceflow or Cursor seamlessly, and ensure LLMs perform reliably in live environments 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 customer adoption of your releases, accelerated resolution times, improved user satisfaction, and a more efficient, faster-moving pipeline. If you want accountability for outcomes, weekly customer interaction, the authority to decline distractions, and the ability to ship what actually moves metrics, this opportunity is for you.

What You Will Be Doing

• Develop and deploy Kayako One capabilities—AI functionality that elevates ticket resolution, integrations with CRM/ticketing platforms, robust and scalable infrastructure, plus performance optimization and defect remediation.
• Facilitate weekly customer discovery sessions to convert genuine pain points into actionable requirements and confirm product strategy with actual users.
• Construct the AI sales automation infrastructure—outreach automation workflows, integration with pipeline and sales tools, automated progression through sales stages, and comprehensive performance analytics.
• Take full ownership of deployment and operational stability—complete stack releases, monitoring/alerting/incident resolution, and management of AWS/database systems.
  
  

What You Won’t Be Doing

• This isn't simply coding to a specification provided by others — you define what to build based on direct customer feedback.
• This isn't work that remains in a staging environment — every feature you create reaches production and serves actual customers.
• This isn't narrow domain specialization — you're accountable for the entire stack, underlying infrastructure, and the complete customer experience.
  
  

Technical Lead Key Responsibilities

• Develop and sustain an AI-powered customer support system that resolves tickets without requiring human intervention
• Develop and sustain a comprehensive AI sales pipeline that manages deals from initial contact through closure
  
  

Basic Requirements

• A minimum of 5 years of professional software development experience
• Proven track record owning complete products or significant systems, beyond individual features
• Demonstrated experience delivering AI/LLM-powered products to production environments (not limited to prototypes or demonstrations)
• Extensive AWS expertise, including Lambda, S3, OpenSearch, RDS, CloudWatch, EventBridge, EC2, Route 53, CloudFront
• Hands-on LLM/AI integration experience, including Claude/ChatGPT prompt engineering, API integration
• Proficiency coding in Python, Java, and JavaScript
• Working experience with MySQL database
• Practical experience using Docker, deployment pipelines, and GitHub workflows
• Experience with OpenAI and JWT API development
• Experience with DNS management and web infrastructure
• Direct customer-facing experience
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5724-TR-COUNTRY-TechnicalLead