AI Experience Engineer (Conversational AI) About the Role: 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 rollout

Optimization:

Review transcripts, recordings and analytics every week, find where conversations fail or transfer, and ship fixes to journey logic, instructions and knowledge

Edge 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 handoff

Containment:

Own containment and CSAT targets per journey, run staged rollouts (1% to 100%), and prioritize the work that moves those numbers most

Product 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 needs

Safety and compliance:

Apply tiered authentication and step-up verification, verbatim compliance language and guardrails against hallucination and off-policy answers

Handoffs:

Design transfers to human agents in Genesys with accurate summaries and auth context

Testing:

Build simulation and regression suites so every journey change ships with evidence it did not break existing behavior

Monitoring:

Watch latency, errors and drop-offs in SumoLogic and Grafana, and own the alerts

Voice tuning:

Latency, filler phrases, interruptions, personality and tone

Sierra relationship:

Be the technical owner on our side, elevate platform issues and shape roadmap asks

What We Look For

3–5 years of Frontend Software Engineering experience, or equivalent experience in Solutions Engineering, Conversational AI or Technical Product roles

Working knowledge of how LLM agents behave: instructions, tool calls, knowledge retrieval, and where each one fails

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 authentication 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

Clear writing and the ability to work with non-engineers in operations,



compliance and legal

Nice 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 handling

Contact center systems such as Genesys, and agent handoff design

Background in fintech or another regulated industry (UDAAP, FDCPA, TCPA, PCI, SOC 2)

What We Offer You

Competitive salary ($140K-$180K CAN) and stock option plan

Paid coverage of medical, dental and vision insurance

Opportunities for qualified growth and development

Paid parental leave

Health & wellness initiatives

Upgrade is dedicated to building a diverse team and an inclusive culture. We believe that it’s crucial to Upgrade’s long-term success to create an environment where all employees feel like they belong and have an equal opportunity to succeed. For this reason, we are asking candidates to voluntarily self-identify through a few demographic questions. Our purpose in collecting this information is to help us assess our outreach efforts and diversity representation goals. Your responses will not be linked to your identity or your application, and neither recruiters nor hiring managers can see this information at an individual level. Your responses are stored in the aggregate and will not play any role in our hiring decision. Your decision to participate or not participate in this survey will have no impact on your candidacy at Upgrade. How you do you identify? (Gender identity) Select...

Are you legally authorized to work in Canada? * Select...

Will you now, or in the future, require sponsorship or employer support to obtain or maintain authorization to work in Canada (e.g., an employer-specific work permit or LMIA)? *

Have you personally designed, built, and launched customer-facing conversational AI journeys (chat or voice) before using platforms such as Sierra, Cognigy, Kore.ai, Dialogflow, or similar? *

#J-18808-Ljbffr

📌 AI Experience Engineer (Conversational AI) (Winnipeg)
🏢 Upgrade
📍 Winnipeg