About the team/role

We are seeking a skilled and detail-oriented AI Conversation Designer to join our Service Design team. This role is central to managing and optimizing our conversational AI agents across multiple modalities, directly impacting customer experience and operational efficiency. The ideal candidate will have hands-on experience with conversational AI platforms, a strong understanding of conversation design principles, and the ability to analyze performance data to drive continuous improvement. This role requires someone who is curious, adaptable, and passionate about leveraging AI to deliver seamless, human-centered support experiences.

What you’ll do

• Lead the development, optimization, and ongoing management of conversational AI agents across modalities, ensuring consistent performance and user experience.
• Own the end-to-end lifecycle of assigned AI agents, including prompt engineering, conversation design, testing, and deployment.
• Drive measurable improvements in agent performance through analysis of key performance indicators and conversation analytics.
• Partner with cross-functional teams to identify automation opportunities and implement solutions that reduce contact volume while maintaining service quality.
• Develop and maintain comprehensive documentation for AI agent workflows and processes.
• Monitor and troubleshoot AI agent behavior, diagnosing issues across conversation flows and escalating technical issues as needed.
• Implement and iterate on dynamic response content, including conditional logic, personalization, and multimedia elements within conversational interfaces.
• Lead special projects as required to support evolving AI capabilities and business needs.

What you bring

• 3-5 years of experience in conversational AI, knowledge management, chatbot administration, or similar roles managing customer-facing digital channels.
• Hands-on experience with conversational AI platforms and understanding of NLU/NLP concepts.
• Proficiency in conversation design principles, including intent mapping, utterance training, and fallback strategies.
• Strong analytical skills with the ability to interpret conversation logs, performance dashboards, and customer feedback to drive optimization.
• Excellent written communication skills and ability to craft clear, concise bot responses for diverse audiences.
• Proven ability to collaborate cross-functionally and translate business requirements into actionable solutions.
• Comfort navigating ambiguity and managing multiple priorities in a fast-paced environment.
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

What you get:

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive compensation and opportunity for advancement
• 100% medical, dental and vision coverage
• Unlimited PTO policy
• Monthly wellness stipend, home office stipend

The Enterprise Support Specialist at Checkr is a pivotal role that combines advanced problem-solving skills with a customer-centric approach. This position requires handling sensitive information with care, swiftly resolving complex issues, and maintaining high-quality support standards. As a subject matter expert, you'll guide team members, contribute to process improvements, and drive innovation in our support services. Your empathy, adaptability, and excellent communication skills will be crucial in delivering exceptional customer experiences that align with Checkr's mission of building a fairer future in the hiring industry. This role offers the opportunity to make a significant impact on our operations while fostering a culture of excellence in customer support.

What you'll do:

• Handle high volumes of customer inquiries via various channels with professionalism
• Deliver exceptional, personalized customer service
• Swiftly resolve complex issues while maintaining quality and meeting deadlines
• Serve as a Subject Matter Expert on products, features, and common issues for your customer portfolio
• Proactively identify and implement operational gaps that impact customer experience 
• Contribute to team knowledge base and training materials for a specialized group of accounts
• Collaborate with cross-functional teams to resolve complex issues
• Maintain strong relationships with key stakeholders, including our Sales, Customer Success, Implementations, Shared Services, and Escalations groups to proactively identify unique customer requirements for our Enterprise and Strategic accounts
• Stay up-to-date with product knowledge and industry trends
• Meet or exceed performance metrics and quality standards
• Support new business initiatives to improve customer and agent experiences
• Handle sensitive information with utmost care and confidentiality
• Generate regular reports on customer issues, trends, candidate outreach, and general support performance
• Serve as a Point of Contact for new onboarding customers and maintain relationship that includes reporting, insights to Success teams, and informing internal team of updates
• Conduct in-depth research to resolve complex customer inquiries
• Analyze data to identify patterns and suggest improvements in support processes
• Assist other Support teams as needed by the business

What you bring:

• 3+ years of experience in a customer-facing role
• Strong written and verbal communication skills
•  Advanced problem-solving and critical thinking abilities
•  Excellent analytical skills to identify root causes and deliver effective solutions
•  Proven track record of handling complex customer inquiries efficiently
•  Ability to navigate ambiguous scenarios and think creatively
•  Customer-centric mindset with high empathy and adaptability
•  Proficiency in CRM systems, support tools, and chat systems
•  Experience in maintaining and improving knowledge bases
•  Familiarity with FCRA standards and compliance (or willingness to learn)
•  Ability to thrive in a fast-paced, ever-changing environment
•  Strong multitasking skills and effective time management
•  Passion for continuous learning and process improvement
•  Comfortable with technology and able to adapt to new tools quickly
•  Strong research skills and attention to detail
•  Ability to synthesize complex information and present findings clearly
•  Team player with a positive attitude and willingness to learn
•  Experience mentoring or guiding team members (preferred)
•  Proficiency in data analysis and reporting tools (preferred)
•  High school diploma or equivalent; Associate's degree preferred
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

What you get:

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive compensation and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to 25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend

#LI-AG1 

About the team/role

As the Staff Knowledge Base Specialist, you will be a senior contributor to the knowledge systems that enable both Checkr's human and digital workers to resolve issues accurately and efficiently. This is a senior individual contributor role within Shared Services, responsible for leading complex, cross-functional knowledge programs that span department boundaries and directly shape the quality of agent-assisted and AI-driven resolution at scale. You will set strategy, clarify goals, and independently drive programs from initiation to measurable outcomes.

Knowledge at Checkr serves a dual audience: human agents who rely on clear, actionable content to resolve complex cases, and AI agents that retrieve, reason over, and act on that same knowledge base autonomously. This role requires mastery of both dimensions. You will design content that is clear and actionable for human agents while simultaneously being structured for accurate AI retrieval, optimized for fast search, and enriched with metadata that drives correct segmentation and response logic. You will also build, manage, and iterate on AI workforce agents that accelerate knowledge operations, treating them as members of your toolkit the same way you would a contractor or vendor.

Our ideal candidate brings a rare combination of disciplines: the precision of a technical writer, the systems thinking of an information architect, and the LLM fluency of a prompt engineer. You have hands-on experience building knowledge for RAG-based AI systems, a sharp instinct for the content gaps that cause agent escalations and model hallucinations, and the ability to drive alignment across engineering, product, quality, and operations partners. You thrive in ambiguity, mentor peers, and balance department impact with broader company objectives. You are startup-minded: comfortable building from scratch, owning ambiguous problems end to end, and leveraging AI agents as force multipliers to drive outcomes at a scale beyond what manual effort allows.

This role is based in Nashville, TN and requires periodic travel (<25%) to connect with teams across Checkr office locations in San Francisco and Denver.

What you'll do

• Design and drive Checkr's agent-facing knowledge architecture: content structure, chunking strategy, metadata schema, retrieval optimization, and decision logic encoding for both human and AI agent consumption.
• Independently lead complex, cross-functional knowledge programs from initiation to delivery, coordinating with product, engineering, quality, and operations stakeholders to set strategy and achieve program goals within planned timeframes.
• Build, deploy, and manage AI workforce agents that execute knowledge operations tasks, including content audits, metadata enrichment, quality checks, and triage workflows, owning agent performance and iterating on prompts, logic, and guardrails to improve outcomes.
• Define and enforce authoring standards that serve a dual audience: content readable and actionable for frontline BPO agents, and structured for accurate, low-latency AI retrieval.
• Design and manage analytical workflows, including AI assisted triage, to surface knowledge gaps from escalation patterns, quality scores, and conversation failure logs.
• Proactively identify and anticipate risks and gaps in the knowledge ecosystem, including content that misleads agents, creates compliance exposure, or degrades AI performance; propose and execute next steps without waiting to be directed.
• Build and maintain metadata frameworks that ensure knowledge is correctly segmented across agent types, customer tiers, product lines, and support workflows.
• Partner with AI/Product and Engineering teams to surface knowledge-side limitations affecting agent and AI resolution quality, influence prompt design, and advocate for platform enhancements.
• Identify opportunities across agent and AI performance data to drive continuous improvements to content standards, knowledge architecture, and intake processes.
• Serve as a trusted cross-functional partner to Quality, Training, Service Design, and frontline operations teams, translating frontline agent experience needs into knowledge improvements.
• Mentor Knowledge team members on agent-aware and AI-aware authoring practices, providing clear, specific feedback and coaching to build team capability.

What you bring

• 5+ years of experience in knowledge management, information architecture, technical writing, or content operations, with demonstrated progression in scope and complexity.
• 2+ years of hands-on experience building knowledge for AI systems, including chunking strategies, metadata design, retrieval accuracy improvement, and hallucination reduction in a RAG-based environment.
• Experience designing content for a dual audience: human agents who need clear, scannable, actionable content and AI systems that require precision structure for accurate retrieval and reasoning.
• Hands-on experience building and managing AI agents or automated workflows (e.g., prompt chains, decision agents, RPA sequences) to execute operational tasks at scale.
• Proven ability to independently lead complex, cross-functional programs, balancing department priorities with broader company objectives and driving outcomes without direct authority.
• Fluency with leading LLMs (GPT-4, Claude, Gemini) and Gen AI concepts including RAG, agentic AI, chain-of-thought prompting, decision flows, and vector search.
• Strong systems thinking: ability to trace how a knowledge gap, metadata error, or unclear procedure propagates into agent escalations, AI failures, and customer experience degradation.
• Analytical mindset with comfort reading quality scores, latency logs, and accuracy data to diagnose root causes and design targeted solutions.
• Track record of proactively identifying risks, leading retrospectives, and implementing process improvements that prevent recurring issues.
• Demonstrated ability to mentor and coach more junior team members; experience leading external contractors is a plus.
• Exceptional written communication: able to produce clear, actionable content for agent-facing audiences and translate complex AI-system concepts into standards and recommendations for varied stakeholders.
• Preferred: Experience with Zendesk or Salesforce knowledge bases.
• Preferred: Background in support operations or conversation design.
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes

What you'll get

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive compensation and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend

Truework, recently acquired by Checkr, provides access to crucial employment and income information needed for mortgage loans, apartment rentals, background checks and more. We are disrupting a $5B+ industry, dominated by legacy incumbents, with a better product and intense customer focus. Within Checkr, Truework operates independently, allowing rapid iteration while also being able to leverage the strengths and assets from our core business. Think of it like joining a startup within a startup!

The Operations team is at the core of Truework’s product fulfillment engine. As an Customer Experience Representative, you will be directly responsible for completing manual verification requests, a critical step in delivering our core product. You will serve as a key driver of revenue by ensuring verifications are completed accurately, quickly, and in compliance with all standards. This is a high-impact, high-volume role that demands precision, professionalism, and persistence. You’ll be engaging directly with employers, payroll providers, and HR contacts to obtain verification data and ensure delivery of time-sensitive products that drive customer satisfaction.

What you’ll do

• Own the end-to-end manual outreach process to fulfill employment and income verifications, ensuring fast and accurate product delivery
• Make outbound phone calls and send written communication to HR and payroll contacts to gather required information in a timely manner
• Conduct discovery and validation work to identify accurate employer contacts, ensuring data integrity and preventing fraudulent or incomplete verifications
• Manage a high volume of outreach activity with new claims and follow ups daily while maintaining top-tier accuracy and documentation
• Navigate internal systems and workflows to complete and submit verifications within defined SLAs
• Collaborate cross-functionally with Customer Support, Quality, and other teams to escalate complex issues and contribute to process improvement

What you bring

• 1+ year of experience in outreach, contact center, sales, fulfillment, or other customer-facing roles; startup or high-growth environments preferred
• Exceptional verbal and written communication skills, with a proven ability to persuade and problem-solve via phone and email
• Strong time management and organizational skills with an ability to juggle multiple priorities in a fast-paced environment
• Self-starter mindset with a drive to hit productivity and fulfillment goals
• Deep sense of ownership over customer and revenue-impacting work, and a commitment to data security, confidentiality, and compliance in every interaction
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

What you’ll get

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive cash and equity compensation and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Flexible PTO policy
• Monthly wellness stipend

#LI-AG1

As the Senior Manager, Enterprise Support, you will own the support experience for Checkr's enterprise customers, driving exceptional service delivery and building scalable support programs that differentiate us in the market. Reporting to the Director of Customer Support, you'll be responsible for enterprise escalations, white-glove support programs, and ensuring our largest customers receive world-class service that drives retention and expansion.

You'll work closely with Customer Success, Sales, and Product teams to translate enterprise customer needs into actionable support strategies. You'll build and lead a team of enterprise support specialists who serve as trusted advisors to our most strategic accounts, handling complex technical inquiries, managing escalations with urgency and expertise, and proactively identifying opportunities to improve the enterprise customer experience.

Our ideal candidate is an experienced enterprise support leader who understands the nuances of supporting complex B2B customers with high-touch service expectations. You have a proven track record of managing enterprise escalations, building premium support programs, and partnering cross-functionally to drive customer outcomes. You're data-driven, operationally excellent, and passionate about leveraging both human expertise and AI capabilities to deliver exceptional support at scale.

This role will require periodic travel (<25%) to connect with teams across Checkr office locations and to visit enterprise customers on-site.

Responsibilities

• Enterprise Support Excellence: Own and optimize the enterprise support experience, ensuring rapid response times, high-quality resolutions, and proactive engagement with our largest customers
• Escalation Management: Serve as the primary point of contact for complex enterprise escalations, coordinating cross-functional resources and driving issues to resolution with appropriate urgency and communication
• Team Leadership: Build, coach, and develop a high-performing team of enterprise support specialists who serve as trusted advisors to strategic accounts
• Premium Support Programs: Design and implement differentiated support offerings for enterprise customers, including dedicated support models, enhanced SLAs, and white-glove service programs
• Cross-Functional Partnership: Collaborate closely with Customer Success, Account Management, Sales, Product, and Engineering teams to ensure seamless enterprise customer experiences and advocate for customer needs
• Voice of Customer: Systematically capture and analyze enterprise customer feedback, translating insights into actionable improvements and product requirements
• Operational Rigor: Establish and monitor enterprise support KPIs (CSAT, SLA adherence, escalation resolution time, etc.), drive continuous improvement, and report on team performance
• Process & Systems: Develop enterprise support playbooks, escalation protocols, and knowledge management systems that enable consistent, high-quality service delivery
• AI Integration: Partner with the Director to implement AI-powered tools that enhance enterprise support efficiency while maintaining the high-touch, personalized service our enterprise customers expect
• Customer Retention: Drive support initiatives that directly impact enterprise NRR (Net Revenue Retention) and reduce churn through exceptional service delivery

What You Bring

• 5+ years of experience in customer support leadership roles, with at least 3 years focused on enterprise B2B customers
• Direct management experience leading teams of 10-20+ support professionals in high-growth environments
• Enterprise support expertise: Deep understanding of enterprise customer expectations, complex multi-stakeholder environments, and premium support models
• Escalation management: Proven track record of successfully managing high-stakes customer escalations and executive-level communications
• Required: Enterprise B2B SaaS experience with complex, technical products
• Preferred: Experience in HR tech, compliance, or background screening industries
• Cross-functional leadership: Strong ability to influence and partner with Sales, Customer Success, Product, and Engineering teams
• Operational excellence: Data-driven approach to decision making with expertise in support metrics, SLA management, and quality assurance
• Systems thinking: Experience building support processes, playbooks, and systems that scale with growth
• Technical acumen: Comfortable supporting technical products and working with engineering teams to resolve complex issues
• Communication skills: Exceptional written and verbal communication, with ability to interact confidently with C-level executives and enterprise stakeholders
• Change agent: Track record of driving continuous improvement and implementing new programs or technologies (including AI tools) in support environments
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes

What You Get

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive compensation and opportunity for advancement
• 100% medical, dental and vision coverage
• Unlimited PTO policy
• Monthly wellness stipend

About Truework

Truework, recently acquired by Checkr, provides access to crucial employment and income information needed for mortgage loans, apartment rentals, background checks, and more. We’re disrupting a $5B+ industry dominated by legacy incumbents and outdated processes. Within Checkr, Truework operates independently, allowing rapid iteration while leveraging the strengths and assets of the core business.

About the Role

This role sits on Checkr’s Operations Insights & Analytics team, directly supporting Truework’s operations team as its primary analytics partner. Truework’s operations are more complex than a typical help desk — and deeply understanding their processes will be central to your success in this role.

Truework already has some operations reporting and data infrastructure in place, but as the first dedicated analyst focused on this work, you’ll own the process of improving and expanding it. Some existing dashboards need to be rebuilt or consolidated, sources-of-truth established, and the team needs reliable performance & cost metrics. You’ll also contribute to the near-term migration from Looker to Omni Analytics.

The ideal candidate is someone who can context-switch between hands-on data work and strategic analysis, thrives in ambiguity, and is energized by making messy things clean. You should be someone who, when given a high-level goal, figures out what questions to ask, what data is needed, and what infrastructure would provide it — and then builds it.

What You’ll Do

Drive Analysis & Business Performance

• Build and maintain models for cost, headcount, and operational performance that inform leadership decisions across Truework operations
• Track and analyze team performance week-over-week, identifying trends, bottlenecks, and opportunities for efficiency gains
• Translate technical findings into clear recommendations for stakeholders at all levels, from operational teams to executive leadership

Build & Improve Reporting

• Define and standardize key operational metrics, working with stakeholders to ensure shared understanding of definitions and methodology
• Consolidate and rebuild existing dashboards, validating data accuracy and filling gaps in coverage
• Build production dashboards and self-service reporting in Omni Analytics, giving Truework’s operations teams reliable visibility into team performance

Strengthen Data Infrastructure

• Improve and expand existing data models to support reliable analytics across Truework’s operations
• Write and maintain dbt models, manage data pipelines, and work with raw database schemas to strengthen analytical foundations
• Identify and fix data quality issues — bad joins, missing records, misaligned definitions — before they become reporting problems
• Contribute hands-on to migrating Truework’s data infrastructure onto Checkr’s systems, working independently to navigate unknowns and solve technical problems as they arise

What You Bring

Required

• 5+ years of experience in analytics, data engineering, or a hybrid role — ideally in a high-growth or startup environment where you’ve had to build things from scratch
• Advanced SQL: complex joins, window functions, CTEs, query optimization. You should be able to navigate unfamiliar database schemas and figure out how data fits together.
• Hands-on experience with data modeling and pipeline tools (dbt, Airflow, or similar). You’ve built and maintained data models, not just queried them.
• Strong BI experience building production dashboards (Looker, Tableau, or similar). You know how to design reporting that’s actually useful, not just comprehensive.
• Comfort working in ambiguous environments with incomplete information. You don’t wait for perfectly defined requirements — you figure out what’s needed and start building.
• Strong communication skills: you can explain technical concepts to non-technical stakeholders and advocate for data quality and infrastructure investments
• An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.

Preferred

• Python for data manipulation, scripting, and statistical analysis
• Experience with data migration projects — moving data between systems, reconciling schemas, validating parity
• Domain experience in operations analytics, fintech, or verification/identity services
• Familiarity with version control (Git) and software engineering practices in an analytics context

What You Get

• A fast-paced and collaborative environment
• Learning and development allowance
• Competitive compensation and opportunity for advancement
• 100% medical, dental, and vision coverage
• Up to $25K reimbursement for fertility, adoption, and parental planning services
• Unlimited PTO policy
• Monthly wellness stipend