Season 7 of Chats with Kent is out: Become a Product Engineer.
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The goal of the Call Kent Podcast is to get my answers to your questions. You record your brief question (120 seconds or less) right from your browser. Then I listen to it later and give my response, and through the magic of technology (ffmpeg), our question and answer are stitched together and published to the podcast feed.
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I look forward to hearing from you!
Kent talks with Dillon Mulroy, Principal Engineer at Cloudflare, about Agent Experience and dogfooding AI platform work: how Cloudflare closes the loop between builders and customers, why observability and support are product superpowers, and how to stay disciplined when agents tempt you to ship huge diffs overnight.
They go deep on watching users work, firehose social feedback, partnering with support, and why “make pain painful” aligns incentives for better software.
0:00 Introduction to Product Engineering 0:53 Dillon's Role at Cloudflare and Agent Experience 2:04 Preparing Cloudflare for Agent Users 5:29 Product Taste and Building What You'd Want to Use 7:09 Building Great Products for Non-Developer Users 10:03 Pushing Back on Pressure to Ship Fast 12:07 Getting Direct Feedback From Users 14:34 Watching Users Work 17:34 Support Teams as a Gold Mine of Product Signal 18:42 Observability, Metrics, and Customer Escalations 20:46 Rebuilding Vercel Domains 22:40 Making User Pain Painful 23:54 Discipline, Small Scope, and Reviewing AI-Written Code 27:52 Observability as Product Engineering 31:00 Delighters and Going Beyond the Basics 37:04 Onboarding Friction and Feedback Loops 40:36 Rewrites, Pain Reduction, and Fixing the Right Problems 44:20 Cross-Functional Relationships Beyond End Users 45:30 Learning Product Sense by Sitting With Support 47:01 Homework: Care Deeply and Build Better Feedback Systems
Dillon’s path runs from internal insurance tools to Vercel Domains to Cloudflare’s agent and dashboard work—always with the same through-line: care about the user, get real feedback, and invest in primitives so delighters don’t collapse under bad foundations. This episode covers metrics and paging as a product habit, learning from customer escalations, scoping small when AI speeds up coding, and building cross-functional relationships (support, sales, finance) as part of engineering judgment.
You’ll hear practical parallels with episodes on delighters and onboarding tension, plus why reviewing agent-written code still matters for system intuition when things break at 2 a.m.
Kent talks with Dillon Mulroy, Principal Engineer at Cloudflare, about Agent Experience and dogfooding AI platform work: how Cloudflare closes the loop between builders and customers, why observability and support are product superpowers, and how to stay disciplined when agents tempt you to ship huge diffs overnight.
They go deep on watching users work, firehose social feedback, partnering with support, and why “make pain painful” aligns incentives for better software.
0:00 Introduction to Product Engineering 0:53 Dillon's Role at Cloudflare and Agent Experience 2:04 Preparing Cloudflare for Agent Users 5:29 Product Taste and Building What You'd Want to Use 7:09 Building Great Products for Non-Developer Users 10:03 Pushing Back on Pressure to Ship Fast 12:07 Getting Direct Feedback From Users 14:34 Watching Users Work 17:34 Support Teams as a Gold Mine of Product Signal 18:42 Observability, Metrics, and Customer Escalations 20:46 Rebuilding Vercel Domains 22:40 Making User Pain Painful 23:54 Discipline, Small Scope, and Reviewing AI-Written Code 27:52 Observability as Product Engineering 31:00 Delighters and Going Beyond the Basics 37:04 Onboarding Friction and Feedback Loops 40:36 Rewrites, Pain Reduction, and Fixing the Right Problems 44:20 Cross-Functional Relationships Beyond End Users 45:30 Learning Product Sense by Sitting With Support 47:01 Homework: Care Deeply and Build Better Feedback Systems
Dillon’s path runs from internal insurance tools to Vercel Domains to Cloudflare’s agent and dashboard work—always with the same through-line: care about the user, get real feedback, and invest in primitives so delighters don’t collapse under bad foundations. This episode covers metrics and paging as a product habit, learning from customer escalations, scoping small when AI speeds up coding, and building cross-functional relationships (support, sales, finance) as part of engineering judgment.
You’ll hear practical parallels with episodes on delighters and onboarding tension, plus why reviewing agent-written code still matters for system intuition when things break at 2 a.m.
Kent talks with Dillon Mulroy, Principal Engineer at Cloudflare, about Agent Experience and dogfooding AI platform work: how Cloudflare closes the loop between builders and customers, why observability and support are product superpowers, and how to stay disciplined when agents tempt you to ship huge diffs overnight.
They go deep on watching users work, firehose social feedback, partnering with support, and why “make pain painful” aligns incentives for better software.
0:00 Introduction to Product Engineering 0:53 Dillon's Role at Cloudflare and Agent Experience 2:04 Preparing Cloudflare for Agent Users 5:29 Product Taste and Building What You'd Want to Use 7:09 Building Great Products for Non-Developer Users 10:03 Pushing Back on Pressure to Ship Fast 12:07 Getting Direct Feedback From Users 14:34 Watching Users Work 17:34 Support Teams as a Gold Mine of Product Signal 18:42 Observability, Metrics, and Customer Escalations 20:46 Rebuilding Vercel Domains 22:40 Making User Pain Painful 23:54 Discipline, Small Scope, and Reviewing AI-Written Code 27:52 Observability as Product Engineering 31:00 Delighters and Going Beyond the Basics 37:04 Onboarding Friction and Feedback Loops 40:36 Rewrites, Pain Reduction, and Fixing the Right Problems 44:20 Cross-Functional Relationships Beyond End Users 45:30 Learning Product Sense by Sitting With Support 47:01 Homework: Care Deeply and Build Better Feedback Systems
Dillon’s path runs from internal insurance tools to Vercel Domains to Cloudflare’s agent and dashboard work—always with the same through-line: care about the user, get real feedback, and invest in primitives so delighters don’t collapse under bad foundations. This episode covers metrics and paging as a product habit, learning from customer escalations, scoping small when AI speeds up coding, and building cross-functional relationships (support, sales, finance) as part of engineering judgment.
You’ll hear practical parallels with episodes on delighters and onboarding tension, plus why reviewing agent-written code still matters for system intuition when things break at 2 a.m.
Kent talks with Dillon Mulroy, Principal Engineer at Cloudflare, about Agent Experience and dogfooding AI platform work: how Cloudflare closes the loop between builders and customers, why observability and support are product superpowers, and how to stay disciplined when agents tempt you to ship huge diffs overnight.
They go deep on watching users work, firehose social feedback, partnering with support, and why “make pain painful” aligns incentives for better software.
0:00 Introduction to Product Engineering 0:53 Dillon's Role at Cloudflare and Agent Experience 2:04 Preparing Cloudflare for Agent Users 5:29 Product Taste and Building What You'd Want to Use 7:09 Building Great Products for Non-Developer Users 10:03 Pushing Back on Pressure to Ship Fast 12:07 Getting Direct Feedback From Users 14:34 Watching Users Work 17:34 Support Teams as a Gold Mine of Product Signal 18:42 Observability, Metrics, and Customer Escalations 20:46 Rebuilding Vercel Domains 22:40 Making User Pain Painful 23:54 Discipline, Small Scope, and Reviewing AI-Written Code 27:52 Observability as Product Engineering 31:00 Delighters and Going Beyond the Basics 37:04 Onboarding Friction and Feedback Loops 40:36 Rewrites, Pain Reduction, and Fixing the Right Problems 44:20 Cross-Functional Relationships Beyond End Users 45:30 Learning Product Sense by Sitting With Support 47:01 Homework: Care Deeply and Build Better Feedback Systems
Dillon’s path runs from internal insurance tools to Vercel Domains to Cloudflare’s agent and dashboard work—always with the same through-line: care about the user, get real feedback, and invest in primitives so delighters don’t collapse under bad foundations. This episode covers metrics and paging as a product habit, learning from customer escalations, scoping small when AI speeds up coding, and building cross-functional relationships (support, sales, finance) as part of engineering judgment.
You’ll hear practical parallels with episodes on delighters and onboarding tension, plus why reviewing agent-written code still matters for system intuition when things break at 2 a.m.
Kent talks with Dillon Mulroy, Principal Engineer at Cloudflare, about Agent Experience and dogfooding AI platform work: how Cloudflare closes the loop between builders and customers, why observability and support are product superpowers, and how to stay disciplined when agents tempt you to ship huge diffs overnight.
They go deep on watching users work, firehose social feedback, partnering with support, and why “make pain painful” aligns incentives for better software.
0:00 Introduction to Product Engineering 0:53 Dillon's Role at Cloudflare and Agent Experience 2:04 Preparing Cloudflare for Agent Users 5:29 Product Taste and Building What You'd Want to Use 7:09 Building Great Products for Non-Developer Users 10:03 Pushing Back on Pressure to Ship Fast 12:07 Getting Direct Feedback From Users 14:34 Watching Users Work 17:34 Support Teams as a Gold Mine of Product Signal 18:42 Observability, Metrics, and Customer Escalations 20:46 Rebuilding Vercel Domains 22:40 Making User Pain Painful 23:54 Discipline, Small Scope, and Reviewing AI-Written Code 27:52 Observability as Product Engineering 31:00 Delighters and Going Beyond the Basics 37:04 Onboarding Friction and Feedback Loops 40:36 Rewrites, Pain Reduction, and Fixing the Right Problems 44:20 Cross-Functional Relationships Beyond End Users 45:30 Learning Product Sense by Sitting With Support 47:01 Homework: Care Deeply and Build Better Feedback Systems
Dillon’s path runs from internal insurance tools to Vercel Domains to Cloudflare’s agent and dashboard work—always with the same through-line: care about the user, get real feedback, and invest in primitives so delighters don’t collapse under bad foundations. This episode covers metrics and paging as a product habit, learning from customer escalations, scoping small when AI speeds up coding, and building cross-functional relationships (support, sales, finance) as part of engineering judgment.
You’ll hear practical parallels with episodes on delighters and onboarding tension, plus why reviewing agent-written code still matters for system intuition when things break at 2 a.m.
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