AI Experience Engineer (Conversational AI)

The company helps customers move in the right direction with affordable and responsible financial products. Since 2017, we’ve helped over 7.5 million customers access over $42 billion in consumer credit. With a relentless focus on improving our customers' financial well-being, we build products that put more money in their pocket and support their journey toward a better financial future. We’re backed by some of the most prominent technology investors and were most recently valued at $7.3B.

We’re consistently recognized for our collaborative and inclusive culture. Most recently, we were named one of the World’s Top Fintech Companies by CNBC, Best Places to Work by Built In, Best Places to Work by the San Francisco Business Times, America’s Greatest Workplaces by Newsweek, Best Startup Employer by Forbes, and Healthiest Employers by Phoenix Business Journal.

We’re looking for new team members who get excited about designing and delivering new and better products. Come join us and help build a better financial future for millions of people.

About the Role

An AI Experience Engineer owns the full lifecycle of the journeys our customers have with the company'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 the company'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 the company'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 the company builds, tests and ships AI experiences.

Our Core Technologies

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.

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% → 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, escalate 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 authorization and permission scopes

• Working knowledge of JavaScript/TypeScript, with the ability to build and maintain coded journeys and integrate APIs within conversational AI platforms.

• 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)

• Conversation design or UX writing experience

What We Offer You

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

• Paid coverage of medical, dental and vision insurance

• Flexible PTO

• Opportunities for professional growth and development
• Paid parental leave

• Health & wellness initiatives

Environmental & Working Conditions

Work is performed indoors in a fast-paced environment that requires the ability to manage multiple priorities and meet established workflows, schedules, and service expectations.

Employees regularly input, retrieve, and exchange information accurately using digital systems and applications to support operational and customer service objectives.

The role requires the ability to receive and exchange information with customers, peers, supervisors, and cross-functional partners through available communication channels, which may include meetings, email, phone, and digital collaboration tools, and may involve real-time, verbal, or in-person exchanges depending on business need.

Job duties may involve managing a high volume of inbound and/or outbound customer interactions and work activities using telecommunications and computer systems. The role requires the ability to read, analyze, and interpret information displayed on computer screens and remain in a working posture for extended periods, consistent with the demands of the position.

Work may be performed in a contact center, office, or remote environment, depending on business needs and the nature of the role. Onsite work environments may include shared workspaces, standard office lighting, and moderate background noise typical of customer service or operational settings.

Employees working remotely are responsible for maintaining a secure and productive workspace with reliable internet connectivity that supports company systems and safeguards the confidentiality of company and customer information.

Reasonable accommodations may be made to enable qualified individuals with disabilities to perform the essential functions of the position in accordance with the Americans with Disabilities Act (ADA) and applicable state and local laws.

We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

Upgrade does not accept unsolicited resumes from staffing agencies, search firms, or any third parties. Any resume submitted to any employee of the company without a prior written agreement in place will be considered the property of the company, and the company will not be obligated to pay any referral or placement fee. Agencies must obtain advance written approval from the company's Talent Acquisition department to submit resumes and only in conjunction with a valid, fully executed agreement.