Kalyan (Kal) Dudala
Oakland, CA · kal@trivialpursuits.dev · LinkedIn
Product builder and systems thinker working at the intersection of AI, interaction design, and real-world workflows. I build AI tools that reduce friction and unlock flow. Everything I build is motivated by the core principle that AI is best used as a thought partner and collaborator, not a substitute. Previously spent 9 years leading platform, data, and developer experience products at VMware and Pivotal across Kubernetes and Cloud Foundry, with a focus on developer productivity, APIs, distributed systems, telemetry and observability, disaster recovery, and data services.
Core Competencies
AI Systems & Applied ML: Claude Code · OpenAI API · Prompt & Interaction Design · RAG pipelines · Fine-tuning · Model evaluation frameworks · Natural Language Understanding · Generative agents · Memory systems
Cloud & Distributed Platforms: Kubernetes · Cloud Foundry · VMware Tanzu · BOSH · AWS · GCP · Reliability engineering, release orchestration, and telemetry pipelines at scale
Product Leadership & Strategy: Roadmapping · Market positioning · Stakeholder alignment · Narrative development · Customer research · Cross-functional team leadership · Hiring & mentorship
Technical Implementation: Python · SQL · TypeScript · React · Node · Distributed architecture design · Observability (Prometheus / Grafana) · Operational automation
Design & Systems Thinking: Human-in-the-loop systems · Interface architectures that preserve flow · Generative & evaluative research · Rapid prototyping · Scenario-driven UX · Multi-modal collaboration design
Experience
Founder
Trivial Pursuits
Created applied AI solutions to a variety of human problems, keeping humans in the loop, sharpening judgment instead of replacing it, and amplifying human creativity and capabilities.
Launched
- Autobiographer (autobiographer.io): A not-for-profit job application tool that analyzes fit, facilitates thoughtful applications and creates tailored application materials.
- Road Not Taken (roadnottaken.io): A popular personalized travel guide generator for road trips that works worldwide.
- Shiny Black Holes (shinyblackholes.com): A semi-autobiographical collaboration between a human songwriter and a generative music model.
In Development
- Saathi: An AI-powered immigration advisor that helps immigrants identify pathways to legal status and naturalization. Open-source version enables legal aid organizations to provide multilingual intake for high-need immigrant communities.
- Chalk (chalk.my): A shared AI-teacher digital workspace designed to alleviate cognitive load for teachers and support differentiated instruction.
Founder
RevMatch.co
Manual sports cars with real mechanical feel are disappearing. RevMatch keeps them on the road and makes them accessible to enthusiasts.
- Bootstrapped a 10-car enthusiast fleet (Porsche 911, Boxster, Cayman, Alfa Romeo Quadrifoglio, Miata, GTI, Wrangler) optimized for driving thrills
- Built to profitability: ~$150K ARR with 25-30% contribution margin
- Designed end-to-end AI operations stack (automated messaging, scheduling, access control, risk screening, route planning) reducing ongoing labor to 0.2 FTE
Lead AI Designer & Developer
SOLVED Consulting
Worked across U.S. and India-based teams to design AI Grading and Feedback capabilities for teachers. The goal was to reduce cognitive overhead so teachers could stay present with students.
- Designed AI grading and feedback agents for Math and ELA (K-12) that matched teacher voice, rubric logic, and instructional intent
- Built the "Agreement / Consistency / Latency / Feedback Quality" evaluation framework for AI-assisted grading
- Created interactive feedback loops where teachers can correct and teach the model
Product Line Manager
VMware Tanzu
- Tanzu Kubernetes Grid Release Lead: Managed release planning, execution, and stakeholder communication. Produced 25% more releases with 50% fewer coordination meetings.
- Tanzu Telemetry & Insights: Developed phone home services for TAS and TKG. Increased customer participation from 35% to 62%.
- Tanzu Observability: Integrated OSS Prometheus and Grafana into out-of-the-box metrics solution.
Staff Product Manager
Pivotal Cloud Foundry
- PCF Untitled: Founded Pivotal's internal zero-to-first-signal prototyping lab. Built working end-to-end prototypes to test hypotheses before committing to productization.
- BOSH Backup & Restore: Conceptualized and led development of the BBR tool for disaster recovery, becoming a cornerstone for platform resilience.
- Ops Manager API: Created robust API removing dependency on GUI interaction. Has since scaled to billions of requests.
Data Scientist & Product Owner
Scholastic Education
- Developed NLP-powered learning aids for struggling readers and designed formative assessment systems for MATH 180 & READ 180
- Revolutionized teacher reporting with just-in-time predictions, growth-over-time displays, and intelligent small group generation tools