Technical Lead
$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 instead of task assignments. This position gives you complete control of an AI product from start to finish: weekly customer meetings, product decision-making, and production deployments. Your dual mandate: 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 business results.

The wider industry isolates engineers from end users behind layers of "process." That's not our approach. No chain of product managers, designers, or customer success teams stands between you and ground truth. You will lead weekly discovery sessions, convert customer pain into working features, deploy rapidly, and track tangible outcomes. You will also create the AI sales automation framework that may serve as the blueprint for Trilogy's portfolio-wide go-to-market motion. Here, your performance is measured by adoption metrics, resolution rates, CSAT scores, and pipeline velocity.

This role means full ownership: new AI capabilities in Kayako One that improve ticket resolution; platform integrations with CRM and ticketing systems; outreach sequences and targeting rules; pipeline connections; analytics that validate impact; plus deployment, monitoring, and on-call responsibilities to maintain uptime. This is not a backend-only position executing specs handed down from others, nor a comfortable lane with neat handoffs. You'll code as the work demands, configure AWS infrastructure with confidence, adopt tools like Voiceflow or Cursor without friction, and make LLMs reliable in production—not just impressive in demos.

You'll operate at the sharp edge of our help desk product and a high-priority AI sales automation initiative, with visibility across the portfolio. Success means customers actively using your releases, shorter resolution times, improved end-user satisfaction, and a more efficient, faster-moving sales pipeline. If you want to own measurable outcomes, engage customers every week, filter out distractions, and ship what actually moves metrics, this is your role.

What you will be doing

  • Develop and deploy Kayako One capabilities—AI-driven ticket resolution improvements, CRM and ticketing platform integrations, scalable and dependable infrastructure, plus performance optimizations and defect fixes.
  • Conduct weekly customer discovery sessions to convert user pain points into feature requirements and confirm product direction with actual users.
  • Create the AI sales automation infrastructure—outreach sequences, pipeline and tool integrations, automated progression through sales stages, and metrics dashboards.
  • Manage deployments and operations—end-to-end releases, monitoring/alerting/incident handling, and AWS/database administration.

What you will NOT be doing

  • This isn't simply coding against a specification someone else prepared — you define what gets built based on direct customer feedback.
  • This isn't work that remains in pre-production environments — your code reaches production and serves live customers.
  • This isn't a narrowly scoped specialty role — you are accountable for the complete stack, underlying infrastructure, and user experience.

Key responsibilities

  • Develop and sustain an AI-powered customer support system that handles tickets without human intervention
  • Develop and sustain a complete AI sales pipeline that moves opportunities 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

Watch Interview
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...

Meet Fabiano

Applying for a role? Here’s what to expect.

Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.

Chat-style
screening interview.
STEP 1

Chat-style
screening interview.

Cognitive 
aptitude test.
STEP 2

Cognitive 
aptitude test.

Prove real-world 
job skills.
STEP 3

Prove real-world 
job skills.

Interview with the hiring manager.
STEP 4

Interview with the hiring manager.

Pass
proctored test.
STEP 5

Pass
proctored test.

Accept job offer.
STEP 6

Accept job offer.

Frequently asked questions

About Crossover

Meet some people who've landed similar jobs

Why Crossover

Recruitment sucks. So we’re fixing it.

The Olympics of work

The Olympics of work

It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.

Premium pay for premium talent

Premium pay for premium talent

Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.

Shortlist by skills, not bias

Shortlist by skills, not bias

We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.

Crossover Logo White
Follow us on
Have a question?

Get answers to common questions using our smart chatbot Crosby.

HELP AND FAQs

Join the world's largest community of AI first Remote WorkersAI-first remote workers.