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 build and own the journeys end to end, from first draft to steady state. 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.
Design and build Sierra journeys in Agent Studio for chat, voice and email, from discovery with operations through production rollout
Review transcripts, recordings and analytics every week, find where conversations fail or transfer, and ship fixes to journey logic, instructions and knowledge
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
Containment: Own containment and CSAT targets per journey, run staged rollouts (1% → 100%), and prioritize the work that moves those numbers most
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
Apply tiered authentication and step-up verification, verbatim compliance language and guardrails against hallucination and off-policy answers
Testing: Build simulation and regression suites so every journey change ships with evidence it did not break existing behavior
Monitoring: Be the technical owner on our side, escalate platform issues and shape roadmap asks
3–5 years of Frontend Software Engineering experience, or equivalent experience in Solutions Engineering, Conversational AI or Technical Product roles
~ Experience building evaluations for non-deterministic systems: test sets, simulations, LLM-as-judge, regression gates
~ Enough technical depth to read API specs, work with backend engineers on REST and GraphQL integrations, and reason about authorization and permission scopes
~ 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
~ Ownership in production: rollouts, monitoring, log analysis and incident response
~ Transparent writing and the ability to work with non-engineers in operations, compliance and legal

ai, Google CCAI, Amazon Lex/Connect)
Voice AI experience: speech-to-text, text-to-speech, latency tuning, barge-in handling
Competitive salary ($140K-$180K CAN) and stock option plan
Paid coverage of medical, dental and vision insurance
Paid parental leave
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📌 AI Experience Engineer (Conversational AI) (Montreal)
🏢 Upgrade
📍 Montreal