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 edgeof 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 DoingDevelop 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 Won’t Be DoingThis 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.Technical Lead Key ResponsibilitiesDevelop and sustain an AI-powered customer support system that handles tickets without human interventionDevelop and sustain a complete AI sales pipeline that moves opportunities from initial contact through closingBasic RequirementsAt least 5 years of professional software development experienceExperience owning entire products or major systems, not just featuresExperience 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, CloudFrontLLM/AI integration experience, including Claude/ChatGPT prompt engineering, API integrationExperience coding in Python, Java, and JavaScriptExperience using MySQL databaseExperience using Docker, deployment pipelines, and GitHub workflowsExperience with OpenAI and JWT API developmentExperience with DNS management and web infrastructureCustomer-facing experienceAbout TrilogyHundreds 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 outstanding 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 usThis 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-CA-COUNTRY-TechnicalLead.001#J-18808-Ljbffr

📌 Technical Lead, Trilogy (Remote) - $200,000/Year Usd - $200,000 A Year - Remote (Toronto)
🏢 Trilogy
📍 Toronto