Remote Senior Escalation Engineer Jobs in Oregon

Five9 is one of the world's leading cloud contact center platforms. Our AI-powered Automated Quality Management (AQM) product is transforming how enterprises measure, evaluate, and improve agent and interaction quality at scale. As we build out our dedicated AQM Prompt Engineering capability within Specialized Services, we are hiring a Senior WEM AQM Prompt Engineer to lead and shape this practice.

This senior role goes beyond hands-on prompt design. You will be the technical authority for Five9 AQM prompt engineering - setting standards, building reusable assets, mentoring the Prompt Engineer team, and acting as the go-to expert for complex customer escalations and pre-sales engagements. If you have spent a significant portion of your career building sophisticated Speech Analytics programs in Verint, NICE, or Genesys - and you have developed serious prompt engineering skills alongside that domain expertise - this role was designed for you.

Why Your Speech Analytics Background is the Foundation for This Role
Building effective AQM prompts follows the same disciplined, iterative methodology that defines expert-level Speech Analytics category design:

At the senior level, this role adds a leadership and practice-building dimension: you will set the standards the rest of the Prompt Engineering team follows and serve as the technical authority across the most complex customer engagements.

Key Responsibilities - Practice Leadership
Serve as the technical lead and subject matter authority for Five9 AQM Prompt Engineering within Specialized Services.
Define and own the prompt engineering methodology, standards, quality gates, and best practice documentation for the team.
Build and maintain a curated, reusable prompt library of validated evaluation templates spanning key verticals and QM use cases.
Mentor and technically guide the WEM AQM Prompt Engineer team (x3), conducting prompt reviews and providing structured feedback.
Drive continuous improvement of the team's prompt design process based on performance data, customer outcomes, and LLM platform developments.

Key Responsibilities - Customer Delivery
Lead prompt engineering on the most complex and high-value AQM customer engagements, from initial scoping through production deployment.
Act as the senior escalation point for prompt performance issues, failure analysis, and remediation on live customer deployments.
Partner with customers at senior stakeholder level to translate QM strategy and compliance requirements into precise, measurable AQM evaluation criteria.
Design and execute prompt validation frameworks - including representative call sampling, precision/recall analysis, and A/B prompt testing - to ensure accuracy before production release.

Key Responsibilities - Product & Pre-Sales Collaboration
Serve as the Prompt Engineering SME in pre-sales engagements, demonstrating Five9 AQM capabilities and advising prospective customers on prompt-driven evaluation design.
Provide structured product feedback to the Five9 AQM product team based on field experience, identifying gaps, limitations, and enhancement opportunities.
Develop and deliver internal training and enablement for consultants and implementation staff on AQM prompt engineering techniques.
Represent the Prompt Engineering practice in cross-functional forums and contribute to go-to-market materials, customer case studies, and thought leadership content.

Key Requirements
Minimum 5 years' hands-on experience as a Speech Analytics Lead, Senior QM Analyst, or WEM Consultant with deep expertise in category/topic design, program governance, and optimization in Verint (Categories/Category Sets), NICE CXne (Category Sets), Genesys (Topics), or equivalent - at a seniority level sufficient to have owned or led an analytics program.
Formal prompt engineering qualification or a verifiable, substantive portfolio of production-grade prompt design work, including evidence of iterative refinement, performance measurement, and documentation.
Demonstrable understanding of LLM behavior - including how prompt structure, instruction framing, persona assignment, chain-of-thought, and few-shot examples affect model outputs.
Strong background in Quality Management design: experience building evaluation frameworks, scorecard design, calibration processes, and QM governance.
Experience leading or mentoring technical team members in a delivery or consulting environment.
Proven track record of translating complex business requirements into structured, testable, and scalable technical solutions.
Excellent written and verbal communication skills; comfortable presenting to senior client stakeholders and internal leadership.
BA/BS or equivalent experience; advanced degree in a relevant discipline is advantageous.

Preferred Qualifications
Formal prompt engineering certification: DeepLearning.AI Prompt Engineering for Developers, Anthropic Prompt Engineering, OpenAI Prompt Engineering, DAIR.AI Prompt Engineering Guide, or equivalent industry-recognized program.
Direct experience with one or more leading LLM platforms at an advanced level (OpenAI GPT-4+, Anthropic Claude, Google Gemini, Meta Llama, or similar), including API usage, system prompt design, and evaluation harness development.
Prior hands-on experience with Five9 AQM or another AI-native QM solution (e.g., NICE Enlighten QM, Genesys Cloud AI Quality, Medallia, Qualtrics).
Experience contributing to or owning a Speech Analytics or QM center of excellence - including methodology documentation, internal training, and cross-client best practice standardization.
Familiarity with prompt evaluation frameworks (e.g., LLM-as-judge, human-in-the-loop evaluation pipelines, or equivalent).
Exposure to NLP concepts - tokenization, embeddings, semantic similarity - sufficient to reason about why a prompt succeeds or fails.
Experience with JSON, Python scripting, or no-code automation tools as applied to prompt testing and workflow automation.
Background in contact center compliance-driven QM (financial services, healthcare, utilities) where regulatory accuracy requirements add additional complexity to evaluation design.

Key Competencies
Technical Authority - recognized internally and externally as the go-to expert on LLM prompt design for contact Centre quality evaluation.
Analytical Rigor - applies statistical thinking and structured measurement to validate and continuously improve prompt performance.
Linguistic Mastery - exceptional command of written instruction; understands how nuance, framing, and ambiguity in prompt language directly influence AI outputs.
Leadership & Coaching - ability to elevate the capability of others through structured mentoring, peer review, and knowledge transfer.
Strategic Customer Engagement - trusted advisor to senior client stakeholders on the use of AI in quality management.
Innovation Orientation - proactively monitors the LLM landscape and identifies opportunities to improve Five9 AQM prompt design practices.
Operational Excellence - drives the team toward repeatable, scalable processes without sacrificing quality or creativity.

About Five9 WEM Specialized Services
The Specialized Services team within Five9 Professional Services delivers expert-led implementation, optimization, and advisory engagements across the Five9 WEM portfolio. Our AQM Prompt Engineering practice is a newly established Centre of excellence, designed to ensure that customers realize the full potential of Five9's AI-powered quality management capabilities. As the founding senior hire into this practice, the Senior WEM AQM Prompt Engineer will have a rare opportunity to define how prompt engineering is done at Five9 - and to build something genuinely new.