About CheckrCheckr is building the data platform to power safe and fair decisions. Checkr’s innovative technology and robust data platform help customers assess risk and ensure safety and compliance to build trusted workplaces and communities. Checkr has over 100,000 customers including Amazon, DoorDash, Netflix, Kimpton, and Anthropic.We’re a team that thrives on solving complex problems with innovative solutions that advance our mission. Checkr is recognized on Forbes Cloud 100 2025 List and is a Y Combinator 2024 Breakthrough Company.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 Pay Transparency Disclosure One of Checkr’s core values is Transparency. To live by that value, we’ve made the decision to disclose salary ranges in all of our job postings. We use geographic cost of labor as an input to develop ranges for our roles and as such, each location where we hire may have a different range. If this role is remote, we have listed the top to the bottom of the possible range, but we will specify the target range for an exact location when you are selected for a recruiting discussion. For more information on our compensation philosophy, see our website. On-target Earnings OR Base Salary range (Nashville, TN) $104,000—$130,000 USD At Checkr, we believe an in office work environment strengthens collaboration, drives innovation, and encourages connection. Our hub locations are Denver, CO; San Francisco, CA; Nashville, TN; and Santiago, Chile. Individuals are expected to work from the office 3+ days a week. In-office perks are provided, such as lunch five times a week, a commuter stipend, and an abundance of snacks and beverages. A relocation stipend may be available for those willing to relocate to a Checkr hub location. Equal Employment Opportunities at CheckrCheckr is committed to building the best product and company, which requires hiring talented and qualified individuals with a diverse set of perspectives and lived experiences. Checkr believes in hiring people of all backgrounds, including those whose histories are impacted by the justice system in accordance with local, state, and/or federal laws, including the San Francisco’s Fair Chance Ordinance. Applicant Privacy PolicyIf you are a California resident or are located in Alberta or British Columbia, our Applicant Privacy Policy applies to our collection and processing of your personal information when you apply for a role with us or otherwise participate in our recruitment process. *Legitimate Checkr emails will always include our official domain name after the @ symbol (e.g., [email protected] or [email protected]).