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.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. 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.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.Our Core Technologies
What You'll Do
Journey creation:
Design and build Sierra journeys in Agent Studio for chat, voice and email, from discovery with operations through production rolloutOptimization:
Review transcripts, recordings and analytics every week, find where conversations fail or transfer, and ship fixes to journey logic,



instructions and knowledgeEdge case handling:
Map the unhappy paths (failed payments, mismatched identity, delinquent accounts, unsupported requests) and make sure each ends in a correct answer or a clean handoffContainment:
Own containment and CSAT targets per journey, run staged rollouts (1% → 100%), and prioritize the work that moves those numbers mostProduct partnership:
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 needsSafety and compliance:
Apply tiered authentication and step-up verification, verbatim compliance language and guardrails against hallucination and off-policy answersHandoffs:
Design transfers to human agents in Genesys with accurate summaries and auth contextTesting:
Build simulation and regression suites so every journey change ships with evidence it did not break existing behaviorMonitoring:
Watch latency, errors and drop-offs in SumoLogic and Grafana, and own the alertsVoice tuning:
Latency, filler phrases, interruptions, personality and toneSierra relationship:
Be the technical owner on our side,
escalate




platform issues and shape roadmap asksWhat We Look For
3–5 years of Frontend Software Engineering experience, or equivalent experience in Solutions Engineering, Conversational AI or Technical Product rolesWorking knowledge of how LLM agents behave: instructions, tool calls, knowledge retrieval, and where each one failsExperience building evaluations for non-deterministic systems: test sets, simulations, LLM-as-judge, regression gatesEnough technical depth to read API specs, work with backend engineers on REST and GraphQL integrations, and reason about authorization and permission scopesProduct and customer mindset: you understand ops procedures, you read transcripts, care about tone, and measure success by whether the customer's problem got solvedOwnership in production: rollouts, monitoring, log analysis and incident responseClear writing and the ability to work with non-engineers in operations, compliance and legalNice To Have
Hands-on experience with Sierra Agent Studio, or a comparable no-code agent platform (Decagon, Ada, Kore.Ai, Google CCAI, Amazon Lex/Connect)Voice AI experience: speech-to-text, text-to-speech, latency tuning, barge-in handlingContact center systems such as Genesys, and agent handoff designBackground in fintech or another regulated industry (UDAAP, FDCPA, TCPA, PCI, SOC 2)What We Offer You
Market-competitive salary ($140K-$180K CAN) and stock option planPaid coverage of medical, dental and vision insuranceOpportunities for professional growth and developmentPaid parental leave
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📌 Ai Experience Engineer (Winnipeg)
🏢 Upgrade
📍 Winnipeg