Kyle Dieruf

Engineering Leader · AI, Search & Consumer Products

Leading by building. I run teams where agents write the code, people own the reasoning, and everyone ships.

  • 2026 AI Excellence Award
  • Agents author nearly every PR
  • Cycle time: weeks → hours or days

Minneapolis, MN

About

I lead Marketplace Search and AI at Cars.com: the core search experience, dealer products, and Carson, the company’s first AI search agent, recognized with a 2026 AI Excellence Award.

I lead as an engineer first. The Agentic Enablement Playbook is the operating model I distilled from leading teams through the shift to agentic-first delivery, starting with Search and AI and scaling to 8 teams across the Marketplace organization. It frees people to spend their time on judgment, taste, and architecture: the work only they can do.

Agents author nearly every pull request. Cycle time has dropped from weeks to hours or days. Every product manager and designer ships code.

Experience

Cars.com

Remote · May 2018 – Present

Senior Software Engineering Manager

Mar 2025 – Present

Leading Marketplace Search and AI: the company’s core search experience, dealer products, and Carson, its first AI search agent.

  • Led delivery of Carson, Cars.com’s AI search agent, recognized with a 2026 AI Excellence Award: 6–8M unique users per month, 25–30% adoption among web searchers, and roughly 20–25% of all web leads, with Carson users converting at meaningfully higher rates from search results to vehicle pages to dealer leads. Delivered by a 7-person team of 4 engineers and 3 data scientists.
  • Led the shift to agentic software delivery, starting with my Search and AI teams and scaling to peer teams across the Marketplace organization, 8 teams in total. Teams ground agents in organizational context (an approach I call Intent Engineering), turn workflows into reusable agent skills, and enforce quality through evals, CI, and policy-as-code. Agents now author nearly every pull request, cycle time has dropped from weeks to hours or days, and every product manager and designer on these teams ships code.
  • Shipped the Cars.com ChatGPT App to production, establishing the company’s first public-facing MCP server and a live presence inside ChatGPT. Delivered without dedicated engineering resources, from stakeholder alignment through AgentCore infrastructure.
  • Drove the formation of a cross-functional AI Engineering team, merging application engineers with Data Science to eliminate organizational silos, and coached Data Science leadership to adopt a rapid, iterative delivery model alongside engineering.
  • Defined the engineering strategy for Carson, including the Vector DB vs. API-Orchestrated GenAI analysis that set its hybrid architecture by showing why vector-only retrieval breaks the ecommerce contract.
  • Led the end-to-end rebuild of the Search Results Page on a server-driven UI (SDUI) architecture across web, iOS, and Android, delivering 14x faster page loads (LCP from 24s to 1.67s at p95).
  • Authored an SEO Execution Plan that turned weeks of bespoke engineering per search pattern into hours of self-service configuration, letting the SEO team operate independently of engineering cycles.
  • Earned 100% positive feedback from my direct reports in the company engagement survey, with every project commitment met and the team operating autonomously through a 10-week manager absence.

Software Engineering Manager

Dec 2022 – Apr 2025

Led mobile and API engineering through rapid growth, establishing the server-driven UI foundations that now power multi-platform delivery.

Senior Software Engineer II / Senior Software Engineer I / iOS Engineer

May 2018 – Dec 2022

Full-stack from day one: led the AWS migration of the web service ecosystem, then served as Lead iOS Engineer and Lead GraphQL Developer on a greenfield platform overhaul, building a new API ecosystem and iOS app end to end.

Humana

Louisville, KY · May 2014 – May 2018

Application Architect / Consultant / Engineer

May 2014 – May 2018

Progressed from intern to architect in four years, leading the Humana Pharmacy app rebuild and its move to Cloud Foundry microservices.

The Agentic Enablement Playbook

The operating model I run: teams that build the machine that builds the product. Agents execute and humans reason. The harness, meaning the context, skills, and gates agents work within, is the product.

01

Ground the Harness

Codify the organization as agent-readable context: architecture, live OKRs, protocols, product definitions, domain boundaries.

02

Map the Human Work

Inventory real workflows and separate human reasoning from clerical execution. Find where judgment actually lives.

03

Codify the Skills

Convert mapped workflows into reusable agent skills. Tribal knowledge becomes infrastructure.

04

Build the Gates

Evals, CI, policy-as-code, protected paths. Quality enforced by construction, not inspection.

05

Open the Domains

Every team accepts contributions from every discipline, across every domain. A breaking contribution is a harness gap, not a contributor failure.

The Full Model

Read the full playbook

Each stage in depth, the maturity ladder, and the norms that make cross-domain contribution work.

Read it →

The result: contributors who operate as leaders across every domain, quality enforced by construction instead of inspection, and a time to market that is structurally reinvented.

Skills

AI & Agentic Systems

AI EnablementAgentic OrchestrationMulti-Agent SystemsMCP ArchitectureContext & Intent EngineeringLLM IntegrationLLM EvalsAI Guardrails & Policy-as-CodeLangChainAWS Bedrock / AgentCore

AI Coding Agents

Claude CodeCursorCodexFactory (Droids)

Leadership

Org DesignTeam ScalingHiringPerformance ManagementOKR-Based PDLC GovernanceAI Strategy & Roadmapping

Search & Consumer Product

OpenSearch / ElasticsearchRelevance TuningSearch ArchitectureServer-Driven UI (SDUI)Web Performance (Core Web Vitals)Native Mobile (SwiftUI, Jetpack Compose)

Technical Stack

PythonTypeScript / JavaScriptReactNext.jsNode.jsGraphQL (Apollo)RESTStreaming APIsSQL

Platform & Observability

AWSCloudflareTerraformGitHub ActionsDataDog (LLM Observability, APM)RudderStackAmplitude

Education

Purdue University

Computer and Information Technology, Information Systems

Graduated May 2016

Let’s connect.

Interested in connecting with engineering and AI leaders building what’s next.

Minneapolis, MN