AI Experience Engineer (Conversational AI)
<p> <strong>Headquarters:</strong> Canada (Remote) </p> <p><span><strong>About the Role:</strong><br><br>An AI Experience Engineer owns the full lifecycle of the journeys our customers have with Upgrade's AI agent on chat, voice and email: creation, optimization, edge case handling and containment growth. They build journeys in Sierra's no-code tooling, partner with Upgrade's product groups to bring their servicing flows to the agent, and are accountable for whether the agent resolves the customer's issue safely, accurately and without a human.</span></p> <p><span>We are hiring an AI Experience Engineer to own Upgrade's customer-facing AI agent. You will sit between engineering, product and customer operations. You will turn servicing workflows, such as making a payment, checking loan details, updating an address or enabling autopay, into production journeys and keep improving them after launch. </span><span>You will build and own the journeys end to end, from first draft to steady state. The work is part builder, part analyst: design the flow, handle the edge cases, read the transcripts, and keep raising containment. Containment, CSAT, transfer quality and hallucination rate are your metrics.</span></p> <p><span>Within your first year, you will own a portfolio of journeys across products (Personal Loans, Card, BNPL, HELOC, Deposits) and help set the standards for how Upgrade builds, tests and ships AI experiences.</span></p> <p> </p> <p><span><strong>Our Core Technologies</strong></span></p> <p><span>Sierra Agent Studio (no-code journeys), Sierra simulations and conversation analytics, GraphQL and REST APIs (as journey tools), Genesys (contact center handoff), SumoLogic, Grafana, SQL, Javascript/Typescript, Claude and other LLM tools.</span></p> <p> </p> <p><span><strong>What You'll Do</strong></span></p> <p><span>• <strong>Journey creation:</strong> Design and build Sierra journeys in Agent Studio for chat, voice and email, from discovery with operations through production rollout</span></p> <p><span>• <strong>Optimization:</strong> Review transcripts, recordings and analytics every week, find where conversations fail or transfer, and ship fixes to journey logic, instructions and knowledge</span></p> <p><span>• <strong>Edge case handling: </strong>Map the unhappy paths (failed payments, mismatched identity, delinquent accounts, unsupported requests) and make sure each ends in a correct answer or a clean handoff</span></p> <p><span>• <strong>Containment:</strong> Own containment and CSAT targets per journey, run staged rollouts (1% → 100%), and prioritize the work that moves those numbers most</span></p> <p><span>• <strong>Product partnership:</strong> Work with product groups (Personal Loans, Card, BNPL, Deposits) to scope new journeys, keep journeys current as products change, and define the APIs the agent needs</span></p> <p><span>• <strong>Safety and compliance:</strong> Apply tiered authentication and step-up verification, verbatim compliance language and guardrails against hallucination and off-policy answers</span></p> <p><span>• <strong>Handoffs:</strong> Design transfers to human agents in Genesys with accurate summaries and auth context</span></p> <p><span>• <strong>Testing:</strong> Build simulation and regression suites so every journey change ships with evidence it did not break existing behavior</span></p> <p><span>• <strong>Monitoring: </strong>Watch latency, errors and drop-offs in SumoLogic and Grafana, and own the alerts</span></p> <p><span>• <strong>Voice tuning:</strong> Latency, filler phrases, interruptions, personality and tone</span></p> <p><span>• <strong>Sierra relationship: </strong>Be the technical owner on our side, escalate platform issues and shape roadmap asks</span></p> <p> </p> <p><span><strong>What We Look For:</strong></span></p> <p><span>• 3–5 years of Frontend Software Engineering experience, or equivalent experience in Solutions Engineering, Conversational AI or Technical Product roles</span></p> <p><span>• Working knowledge of how LLM agents behave: instructions, tool calls, knowledge retrieval, and where each one fails</span></p> <p><span>• Experience building evaluations for non-deterministic systems: test sets, simulations, LLM-as-judge, regression gates</span></p> <p><span>• Enough technical depth to read API specs, work with backend engineers on REST and GraphQL integrations, and reason about authorization and permission scopes</span></p> <p><span>• Working knowledge of JavaScript/TypeScript, with the ability to build and maintain coded journeys and integrate APIs within conversational AI platforms.</span></p> <p><span>• Product and customer mindset: you understand ops procedures, you read transcripts, care about tone, and measure success by whether the customer's problem got solved</span></p> <p><span>• Ownership in production: rollouts, monitoring, log analysis and incident response</span></p> <p><span>• Clear writing and the ability to work with non-engineers in operations, compliance and legal</span></p> <p> </p> <p><span><strong>Nice To Have:</strong></span></p> <p><span>• Hands-on experience with Sierra Agent Studio, or a comparable no-code agent platform (Decagon, Ada, Kore.ai, Google CCAI, Amazon Lex/Connect)</span></p> <p><span>• Voice AI experience: speech-to-text, text-to-speech, latency tuning, barge-in handling</span></p> <p><span>• Contact center systems such as Genesys, and agent handoff design</span></p> <p><span>• Background in fintech or another regulated industry (UDAAP, FDCPA, TCPA, PCI, SOC 2)</span></p> <p><span>• Conversation design or UX writing experience</span></p> <p> </p> <p><span><strong>What We Offer You: </strong></span></p> <p><span>• Competitive salary ($140K-$180K CAN) and stock option plan</span></p> <p><span>• Paid coverage of medical, dental and vision insurance </span></p> <p><span>• Flexible PTO</span></p> <p><span>• Opportunities for professional growth and development<br>• Paid parental leave</span></p> <p><span>• Health & wellness initiatives</span></p> <p><strong>To apply:</strong> <a href="https://weworkremotely.com/remote-jobs/upgrade-ai-experience-engineer-conversational-ai">https://weworkremotely.com/remote-jobs/upgrade-ai-experience-engineer-conversational-ai</a></p>
About Upgrade
Upgrade is a fintech company that provides affordable and responsible financial products to help customers improve their financial well-being.
Since 2017, the company has served over 7.5 million customers and facilitated over $42 billion in consumer credit. Upgrade's primary product offering includes Flex Pay, a consumer credit solution that enables customers to access affordable financing through various sales channels and merchant partners.
The company is backed by prominent technology investors and was valued at $7.3 billion, with recognition as one of the World's Top Fintech Companies by CNBC and multiple awards for workplace culture and employer quality.
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