Kyle Dieruf

Leading Marketplace Search and AI: the company’s core search experience and first conversational AI product.

• Led delivery of Carson, Cars.com’s AI-powered search product recognized with a 2026 AI Excellence Award, serving 6–8M unique users per month with 25–30% adoption among web searchers. Carson users convert at meaningfully higher rates across the SRP-to-VDP and VDP-to-Lead funnel, with Carson generating roughly 20–25% of all web leads. Delivered by a 7-person cross-functional team of 4 engineers and 3 data scientists.
• Pioneered the practice of Intent Engineering, an agentic-first approach to organizational AI enablement. By grounding AI agents in live company OKRs, architecture context, and domain knowledge, the approach enables agents to make product-aware decisions without human handholding. Adopted across multiple teams.
• Built Cars.com’s enterprise ChatGPT integration, establishing the company’s first public-facing MCP server. Leveraged Intent Engineering to deliver at engineering depth and pace without dedicated engineering resources, managing full project delivery from stakeholder coordination through AgentCore infrastructure standup.
• Drove the formation of a cross-functional AI Engineering team, merging application engineers with Data Science to eliminate organizational silos. Coached Data Science leadership through influence to adopt a rapid, iterative delivery model alongside engineering.
• Resolved production incidents end-to-end without pulling the team in reactively, using Intent Engineering to assess DataDog telemetry and diagnose issues across multiple codebases, delivering engineer-reviewed solutions directly.
• Authored the Carson Roadmap and Strategy, a 5-phase AI investment plan establishing the department’s technical direction and competitive positioning against CarGurus, Amazon, and Google Shopping. Referenced by product and engineering leadership for prioritization decisions.
• Conducted the Vector DB vs. API-Orchestrated GenAI strategic analysis that determined Cars.com’s hybrid AI architecture, demonstrating why vector-only approaches break the ecommerce contract and positioning the company against Amazon, Google Shopping, and CarGurus Discover.
• Led the end-to-end rebuild of the Search Results Page using SDUI architecture across web, iOS, and Android, delivering 14x LCP improvement (24s to 1.67s at p95), 3x FCP improvement (4.3s to 1.28s), and 4.5x DOM Time to Interactive improvement vs. the legacy platform.
• Authored a 5-phase SEO Execution Plan transforming SEO from weeks of bespoke engineering per search pattern to hours of self-service configuration, enabling the SEO team to operate independently of engineering cycles.
• Achieved 100% positive feedback from all 10 direct reports in the company engagement survey, with all project commitments met and the team operating autonomously through a 10-week manager absence.
• Navigated significant organizational complexity alongside product delivery, rescuing a stalled cross-team project to MVP, coaching the owning EM to full ownership, and managing a senior-level personnel transition with zero impact on delivery commitments.