Senior AI Engineer, Trilogy (Remote) - $200,000/year USD

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Senior AI Engineer, Trilogy (Remote) - $200,000/year USD

Crossover

Engineering & Technology

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Job descriptions & requirements

You're a full‑stack product engineer who thrives on ownership rather than task lists.

This roleputs you in charge of an AI product from start to finish: engaging with customers every week, deciding the roadmap, and deploying to production.

Your dual focus: enable Kayako One to resolve support tickets autonomously and construct an AI‑driven sales pipeline that moves prospects from initial contact to closed deal.

You own the technology stack, the product direction, the release schedule, and the business results.

The broader industry isolates engineers from end users behind layers of "process." We reject that model.

No intermediary chain of product managers, designers, or customer success teams stands between you and the field.

You'll lead weekly discovery sessions, convert customer challenges into product requirements, release iteratively, and track measurable outcomes.

You'll also build the AI sales automation framework that may serve as the blueprint for Trilogy's portfolio‑wide go‑to‑market.

Here, success is measured by adoption metrics, resolution rates, customer satisfaction scores, and pipeline velocity.

This position means owning the entire system: developing new AI capabilities in Kayako One to improve ticket resolution; building integrations with CRM and ticketing systems; designing outreach workflows and targeting algorithms; creating pipeline connectors; producing reports that validate effectiveness; and managing deployments, monitoring, and incident handling to ensure uptime.

This is not a backend‑only role executing pre‑defined tickets, nor a comfortable lane with hand‑offs.

You'll write production code as required, configure AWS infrastructure expertly, adopt tools such as Voiceflow or Cursor seamlessly, and ensure LLMs perform reliably in production rather than merely impressing in demos.

You'll operate at the leading edge of our help desk product and an AI sales automation initiative, with visibility across the portfolio.

Success means customers actively use your releases, resolutions accelerate, end users report higher satisfaction, and the pipeline becomes cleaner and faster.

If you want to own business outcomes, engage with customers weekly, filter out distractions, and ship what truly moves the needle, this opportunity is for you.

What You Will Be Doing

• Develop and deploy Kayako One capabilities—AI‑powered ticket resolution improvements, CRM and ticketing platform integrations, scalable and reliable infrastructure, plus performance optimizations and bug remediation.

• Conduct weekly customer discovery sessions to extract genuine pain points, translate them into product requirements, and validate direction with real users.

• Construct the AI sales automation platform—design outreach workflows, integrate pipeline and sales tools, automate stage progression, and build performance dashboards.

• Manage deployment and operational excellence—execute full‑stack releases, implement monitoring/alerting/incident response, and maintain AWS infrastructure and database systems.

What You Won’t Be Doing

• This is not simply coding to specifications given to you — you define what gets built based on direct customer feedback.

• This is not work that remains in staging environments — every feature you create reaches production and real users.

• This is not narrow technical specialization — you are accountable for the entire stack, infrastructure, and end‑user experience.

Senior AI Engineer Key Responsibilities

• Develop and sustain an AI‑powered customer support system capable of resolving tickets without human intervention

• Develop and sustain a complete AI sales pipeline that advances opportunities from initial contact through deal closure

Basic Requirements

• Minimum 5 years of professional software development experience

• Track record of owning complete products or major systems, not merely isolated features

• Proven history of shipping AI/LLM‑powered products to production (beyond prototypes or demonstrations)

• Extensive AWS expertise, including Lambda, S3, OpenSearch, RDS, CloudWatch, EventBridge, EC2, Route 53, CloudFront

• Hands‑on LLM/AI integration work, including Claude/ChatGPT prompt engineering and API integration

• Proficiency in Python, Java, and JavaScript

• Working knowledge of MySQL database

• Practical experience with Docker, deployment pipelines, and GitHub workflows

• Familiarity with OpenAI and JWT API development

• Experience managing DNS 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-NG-COUNTRY-SeniorAIEngine

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