Kyle Dieruf
Engineering Leader · Search, AI & Consumer Products
Minneapolis, MN
About
I lead engineering teams and build alongside them, from domain modeling and product design to architecture and implementation.
My Agentic Enablement Playbook describes how I prepare codebases and delivery systems so people across disciplines can build with agents.
Experience
Cars.com
Remote · May 2018 – Present
Mar 2025 – Present
Lead engineering and technical direction for Marketplace Search and AI, spanning core search, dealer products, and Carson.
- Initiated and led delivery of Carson, Cars.com’s AI search agent and a 2026 AI Excellence Award winner, generating roughly 20–25% of web leads.
- Rebuilt search around shared server-driven UI APIs for web and fully native iOS and Android apps; reduced web p95 LCP from 24s to 1.67s.
- Made new search-page types self-service for the SEO team, replacing weeks of engineering work.
- Shipped the Cars.com ChatGPT App and the company’s first public MCP server without a dedicated engineering team.
- Rebuilt team delivery around agent-ready codebases and enforced guardrails, enabling 10+ production deployments per week at approximately 5% change fail rate.
- Built the agent harness and drove adoption across 8 Marketplace teams through hands-on pairing and coaching for engineers, product managers, and designers.
- Established an engineering culture of product ownership and business acumen, turning ideas like Market Area Expansion into significant new revenue streams.
Dec 2022 – Mar 2025
Led mobile and API engineering.
- Grew mobile and API engineering from 4 to 16 engineers, added a Product Manager and second Engineering Manager, and organized delivery into autonomous pods.
- Set the mobile product and architecture strategy: fully native iOS and Android apps backed by shared, server-driven APIs, preserving familiar OS design patterns and native integrations.
iOS Engineer → Senior Software Engineer II
May 2018 – Dec 2022
Designed and built the GraphQL platform that enabled a new native mobile stack and exposed canonical Marketplace data to internal teams and third-party integrations. Led the AWS migration of web services in my first year.
Humana
Louisville, KY · May 2014 – May 2018
Intern → Application Architect
May 2014 – May 2018
Led the rebuild of the Humana Pharmacy app and moved its APIs to Cloud Foundry microservices.
The Agentic Enablement Playbook
How I take a team from using AI tools to building and running products with agents, in six stages.
Give agents business and codebase context
Make domain models, product goals, architecture, and engineering standards discoverable and keep them current.
Map the work
List the team’s real workflows and sort the steps that need judgment from the busywork.
Turn workflows into agent loops
Encode each workflow so agents can run it, first as skills people invoke, then as deployed agents that run on their own.
Build quality gates
Add evals, CI, and policy checks so quality doesn’t depend on someone catching mistakes in review.
Let everyone contribute
Enable contributions across disciplines with shared context, clear ownership, and the same quality standards.
Let agents watch what you ship
Have agents monitor system health, experiment results, and business analytics, and turn what they find into fixes and improvements.
Skills
Leadership
Search & Consumer Product
AI & Agentic Systems
Technical Stack
Platform & Observability
Education
Purdue University
Computer and Information Technology, Information Systems
Graduated May 2016
Let’s connect.
Always happy to talk shop with other engineering and AI leaders.
Minneapolis, MN