2026-03-25 20:03:34
Steve Kaliski is a software engineer at Stripe who has spent the past six and a half years building developer tools and payment infrastructure. He’s part of the team that created “minions”—Stripe’s internal AI coding agents, which now ship approximately 1,300 pull requests per week with minimal human intervention beyond code review. In this episode, Steve demonstrates how Stripe engineers activate development work from Slack and leverage cloud-based development environments for parallel agent workflows, and demos machine-to-machine payments where AI agents transact autonomously with third-party services.
Listen or watch on YouTube, Spotify, or Apple Podcasts
How Stripe’s “minions” write 1,300 pull requests per week with minimal human intervention
Why a good developer experience for humans creates better outcomes for AI agents
The critical role of cloud development environments in unlocking AI-powered engineering velocity
The machine payment protocol that lets AI agents spend money to accomplish tasks
The code review strategy for handling thousands of agent-written PRs
Why non-engineers at Stripe are starting to use minions to ship code
The future of software businesses built primarily for agent consumers
Optimizely—Your AI agent orchestration platform for marketing and digital teams
Rippling—Stop wasting time on admin tasks, build your startup faster
(00:00) Introduction to Steve
(02:39) Stripe’s minions and their effect on Stripe as a whole
(04:42) Why activation energy matters more than execution
(05:44) What is a minion? The technical architecture
(06:52) Demo: Activating a minion from Slack with an emoji
(09:04) Why good developer experience benefits both humans and agents
(11:22) Walking through the agent loop and system prompts
(13:42) Why Stripe chose Goose as their agent harness
(16:00) The role of Stripe’s developer productivity team
(17:15) Why cloud environments unlock multi-threaded AI engineering
(21:14) One-shot prompting: from Slack to shipped PR
(22:04) How Stripe handles code review for 1,300 AI-written PRs weekly
(23:44) Non-engineers using minions across the company
(24:53) Demo: Planning a birthday party with Claude and machine payments
(32:15) Quick recap
(35:08) The future of ephemeral, API-first businesses for agents
(36:36) Lightning round and final thoughts
• Goose (AI agent harness): https://github.com/block/goose
• Claude Code: https://claude.ai/code
• Cursor: https://cursor.sh/
• VS Code: https://code.visualstudio.com/
• Slack: https://slack.com/
• Browserbase: https://browserbase.com/
• Parallel AI: https://www.parallel.ai/
• PostalForm: https://postalform.com/
• Stripe Climate: https://stripe.com/climate
• Stripe machine payments: https://docs.stripe.com/payments/machine
• Blue-Green Deployment: https://martinfowler.com/bliki/BlueGreenDeployment.html
• Git worktrees: https://git-scm.com/docs/git-worktree
Twitter: https://twitter.com/stevekaliski
LinkedIn: https://www.linkedin.com/in/steve-kaliski-079a7710/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-03-24 20:45:12
👋 Hey there, I’m Lenny. Each week, I answer reader questions about building product, driving growth, and accelerating your career. For more: Lenny’s Podcast | Lennybot | How I AI | My favorite AI/PM courses, public speaking course, and interview prep copilot
P.S. Get a full free year of Lovable, Manus, Replit, Gamma, n8n, Canva, ElevenLabs, Amp, Factory, Devin, Bolt, Wispr Flow, Linear, PostHog, Framer, Railway, Granola, Warp, Perplexity, Magic Patterns, Mobbin, ChatPRD, and Stripe Atlas by becoming an Insider subscriber. Yes, this is for real.
Welcome to our biannual State of the Product Job Market—our fourth and, very surprisingly, the most optimistic. In spite of the headlines about layoffs and AI taking jobs, we’re actually seeing a lot of promising signs in tech hiring, and some interesting new trends:
PM openings are at the highest levels we’ve seen in over three years
AI hasn’t slowed the demand for software engineers (at least not yet)
AI roles in general are absolutely exploding
Design roles have plateaued
The Bay Area is increasing in importance
Remote work opportunities continue to decline
Despite ongoing layoffs, the overall number of tech jobs continues to grow
While these numbers are promising, I know a lot of people are having a hard time finding a job right now. And more openings doesn’t automatically mean people are finding jobs more quickly. For anyone in that situation, first of all, I’m sorry. Second, I’m working on ways to help. Until then, check out the end of this post for a bunch of resources I’ve collected that’ll improve your odds of landing a gig.
Let’s get into it.
This analysis is based on data from TrueUp, one of my favorite collaborators and sources of data. They track job openings at tech companies and top startups around the world (over 9,000 companies) and make it easy to browse open gigs. Their data looks at roles at tech companies—the most sought-after and lucrative jobs. (It doesn’t include roles at non-tech companies and consulting agencies.)
There are over 7,300 open PM roles at tech companies globally, and trending up. This is 75% above the low we saw in early 2023, and already up nearly 20% since the start of this year. Today we have the most open PM roles we’ve seen since 2022. (You can see all of these open roles here.)
The same trend is true for engineering roles . . .
There are over 67,000 (!!!) eng openings at tech companies globally right now, with 26,000 just in the U.S. We don’t know if there would have been more open roles if not for AI or if AI is actually leading to more open roles, but since the start of this year, the increase in open eng roles is accelerating even more.
If you’re skeptical that this growth is real and likely to be sustained, we’re also seeing a surge in demand for tech recruiters. The number of open recruiter roles is almost back to 2022 peak levels. This role got hit the hardest post-Covid, and also recovered the quickest. By definition, recruiting headcount expands and contracts with hiring demand, so it’s likely a leading indication that we’re tracking toward sustained highs in hiring demand in tech.
AI roles were already growing fast in our last update mid-last year, but they are now hockey-sticking:
“AI roles” includes (1) all open roles at AI-driven companies, like OpenAI, Anthropic, Cursor, and Lovable, and (2) AI-specific roles at non-AI companies, like an AI PM at Figma. Browse them here.
Demand for AI engineers and AI PMs is similarly exploding.
Whether this is simply the number of AI companies being created or the headcount at top AI companies growing, it’s a good time to be in AI.
Unlike PM and engineering, open design jobs have been relatively flat since early 2023, and there are also fewer of these roles than PMs and engineers in absolute terms (about 5,700 globally).
I don’t know exactly what’s going on here, but it does feel AI-related. Unlike PM and eng, which started growing in 2024 (two years post-ChatGPT), design didn’t. If I had to venture a theory, I’d say that because AI is allowing engineers to move so quickly, there’s less opportunity—and less desire—to involve the traditional design process. A recent tweet commented on this same trend. That said, you’d think design would become a differentiator as more products compete for attention. Something to think about for your company! We’ll keep watching this trend and AI’s impact on org design more generally.
One interesting observation we made when we went a level deeper: the ratio of demand for PMs vs. designers has flipped. In mid-2023, we went from more open designer roles to more open PM roles. And ever since, PM demand has been pulling away (currently 1.27x). This will be another trend to monitor, in terms of how AI is reshaping org design.
The Bay Area has long had the highest share of tech roles, but that share is still growing. Over 20% of all eng and designer roles are now in the Bay Area, and over 23% (!!!) of open PM roles are too (up 50% since 2022!). And all three are still going up.
A whopping third of open AI roles are based in the Bay Area, but, interestingly, this number has stayed relatively flat in the past few years. That tells me that the Bay Area unquestionably continues to be the center of AI (the next city is New York, with 10.2%), but at the same time, AI roles outside the Bay Area continue to grow at the same rate.
One more interesting data point: NYC has established itself as the #2 tech jobs location in the world, despite not being the headquarters of any of the leading tech companies. Bengaluru (formerly Bangalore), London, Tel Aviv, and Singapore continue to be the top international hubs for tech.
2026-03-24 17:02:05
If you’re a premium subscriber
Add the private feed to your podcast app at add.lennysreads.com
Contrary to what the headlines might be telling you, PM job openings are at their highest point in over three years, AI roles are hockey-sticking, and tech headcount is growing. Today’s episode is our fourth biannual update on the tech job market (the most optimistic yet) and breaks down seven key trends shaping the job landscape right now.
In this episode, you’ll learn:
Why PMs have reason to be optimistic
How the influx of new AI roles is shaping the industry
The unexpected sign of tech growth
What current job openings look like for design and software engineering roles
Surprising trends across remote job opportunities
References:
2026-03-23 23:02:35
Brought to you by:
Marco Casalaina, VP of Core AI Products at Microsoft, walks through how he uses Warp, Microsoft 365 Copilot, and ChatGPT to spin up lightweight “micro-agents” on the fly that handle everything from Azure admin to document scanning to video compression.
Listen now on YouTube • Spotify • Apple Podcasts
Automation frees you to focus on higher-value activities. As Marco puts it: “I do something else while these agents are doing whatever it is I need them to do.” When scanning his daughter’s homework, he was able to help her with math problems instead of fighting with scanner software.
Hardware automation is an underappreciated AI use case. Marco demonstrates how Warp can control his scanner through NAPS2, a CLI tool for scanners. This allows him to scan documents, flip pages, and combine PDFs without ever touching the scanner software.
File manipulation is a powerful AI capability. When Marco needed to compress a 1.7GB video file, he simply asked Warp to analyze why it was so large and re-encode it with FFmpeg. The AI identified the issue (excessive bitrate and resolution) and compressed it to 13MB while maintaining quality.
Ad hoc agents are changing how we approach automation. Marco defines these as “unnamed agents created on the fly to do something for me.” Rather than building complex, permanent workflows, these micro-agents handle specific tasks when needed and then disappear. This approach is becoming a trend across general-purpose AI tools, blurring the line between consuming and building agents.
CLI tools with AI create better interfaces than traditional GUIs. Marco points out that designing graphical interfaces for complex systems like Azure permissions is extremely difficult. AI with access to command-line tools can abstract away these design challenges.
How Microsoft’s AI VP Automates Everything with 5 Micro-Agent Workflows: https://www.chatprd.ai/how-i-ai/microsofts-ai-vp-automates-everything-with-5-micro-agent-workflows
How to Create an Automated Meeting Scheduler with Microsoft 365 Copilot: https://www.chatprd.ai/how-i-ai/workflows/how-to-create-an-automated-meeting-scheduler-with-microsoft-365-copilot
How to Scan and Merge Two-Sided Documents into a Single PDF with AI: https://www.chatprd.ai/how-i-ai/workflows/how-to-scan-and-merge-two-sided-documents-into-a-single-pdf-with-ai
How to Automate Azure User Role Management with AI in the Terminal: https://www.chatprd.ai/how-i-ai/workflows/how-to-automate-azure-user-role-management-with-ai-in-the-terminal
If you’re enjoying these episodes, reply and let me know what you’d love to learn more about: AI workflows, hiring, growth, product strategy—anything.
Catch you next week,
Lenny
P.S. Want every new episode delivered the moment it drops? Hit “Follow” on your favorite podcast app.
2026-03-23 20:01:26
Marco Casalaina, VP of Core AI Products and AI Futurist at Microsoft, demonstrates how he uses AI tools to automate administrative tasks that typically consume valuable time. Rather than using Warp as a coding assistant (its primary marketed purpose), Marco leverages it to manage Azure resources, scan documents, compress videos, and more. He shows how these “micro-agents” can reduce friction in everyday workflows, allowing him to focus on higher-value activities. Marco also demonstrates how Microsoft 365 Copilot and ChatGPT can create triggered workflows that respond to emails or check for information on a schedule, highlighting how the line between consuming and building AI agents is blurring.
Listen or watch on YouTube, Spotify, or Apple Podcasts
How to use Warp to manage Azure resources and assign permissions without navigating complex web interfaces
Techniques for automating document scanning and processing directly from the terminal
Methods for analyzing and compressing video files using AI-generated FFmpeg commands
How to create simple rules that dramatically improve AI performance for specialized tasks
Ways to build triggered workflows in Microsoft 365 Copilot that automatically respond to emails
How to configure ChatGPT to perform scheduled tasks like checking for new content
Strategies for creating consistent AI interactions using AutoHotkey shortcuts
Rovo—AI that knows your business
Lovable—Build apps by simply chatting with AI
(00:00) Introduction to Marco Casalaina
(02:14) Why Marco chose Warp for administrative tasks
(03:57) Demo: Using Warp to manage Azure resources and permissions
(06:00) How CLI tools eliminate GUI friction for complex tasks
(07:18) Creating rules to improve AI performance for specialized tasks
(10:28) Demo: Document scanning automation
(13:00) Combining odd and even pages using a Python automation
(15:04) The value of ephemeral AI solutions vs. permanent tools
(17:12) Video compression using FFmpeg commands
(20:22) The concept of “ad hoc agents” for specific tasks
(22:31) Demo: Creating triggered workflows in Microsoft 365 Copilot
(25:51) Demo: Setting up scheduled tasks in ChatGPT
(27:17) How AI automation changes time management
(29:14) Teaching AI skills to the next generation
(30:30) Strategies for improving AI performance with AutoHotkey
• Warp: https://www.warp.dev/
• Microsoft Azure: https://azure.microsoft.com/en-us
• Azure CLI: https://learn.microsoft.com/en-us/cli/azure/
• Microsoft 365 Copilot: https://www.microsoft.com/en-us/microsoft-365/copilot
• ChatGPT: https://chat.openai.com/
• NAPS2: https://www.naps2.com/
• PyPDF2: https://pypdf2.readthedocs.io/
• FFmpeg: https://ffmpeg.org/
LinkedIn: https://www.linkedin.com/in/marcocasalaina/
ChatPRD: https://www.chatprd.ai/
Website: https://clairevo.com/
LinkedIn: https://www.linkedin.com/in/clairevo/
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
2026-03-22 20:31:51
Jessica Fain is a product leader at Webflow and former Chief of Staff to the CPO at Slack, where she worked alongside April Underwood and many past podcast guests including Stewart Butterfield, Annie Pearl, Tamar Yehoshua, and Noah Weiss. She’s spent her career learning how executives actually make decisions—and why most people completely misunderstand the process.
Listen on YouTube, Spotify, and Apple Podcasts
Why great ideas often don’t get buy-in
Why executive calendars are “like strobe lights” and why the first 30 seconds of a meeting matter so much
Why executives are usually optimizing for a global maximum while you are often optimizing locally
The best question Jessica uses when a leader says something that seems wrong: “That’s so interesting. What led you to believe that?”
Why you should go in to learn, not to convince
Why showing only one option is a mistake
Why AI will make influence more important, not less
Omni—AI analytics your customers can trust
Lovable—Build apps by simply chatting with AI
Vanta—Automate compliance, manage risk, and accelerate trust with AI
• LinkedIn: https://www.linkedin.com/in/jessica-fain-79b8989
• Box: https://www.box.com
• Slack: https://slack.com
• Brightwheel: https://mybrightwheel.com
• Webflow: https://webflow.com
• April Underwood on LinkedIn: https://www.linkedin.com/in/aprilunderwood
• Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack): https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua
• Atlassian: https://www.atlassian.com
• Behind the scenes of Calendly’s rapid growth | Annie Pearl (CPO): https://www.lennysnewsletter.com/p/behind-the-scenes-of-calendlys-rapid
• Calendly: https://calendly.com
• Glassdoor: https://www.glassdoor.co.in/index.htm
• The 10 traits of great PMs, how AI will impact your product, and Slack’s product development process | Noah Weiss (Slack, Foursquare, Google): https://www.lennysnewsletter.com/p/the-10-traits-of-great-pms-how-ai
• Ethan Eismann on X: https://x.com/eeismann
• Slack founder: Mental models for building products people love ft. Stewart Butterfield: https://www.lennysnewsletter.com/p/slack-founder-stewart-butterfield
• Ilan Frank on LinkedIn: https://www.linkedin.com/in/ilanfrank
• Checkr: https://checkr.com
• Ali Rayl on LinkedIn: https://www.linkedin.com/in/alirayl
• Rachel Wolan on LinkedIn: https://www.linkedin.com/in/rachelwolan
• How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan: https://www.lennysnewsletter.com/p/how-webflows-cpo-built-an-ai-chief
• Barbara Minto’s website: https://www.barbaraminto.com
• How Slack invests in big little details through Customer Love Sprints: https://slack.design/articles/sweating-the-small-stuff
• Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein
• The Enneagram Institute: https://www.enneagraminstitute.com/type-descriptions
• The Pitt on Prime Video: https://www.amazon.com/The-Pitt-Season-1/dp/B0DNRR8QWD
• Towel warmer: https://www.amazon.com/FLYHIT-Large-Towel-Warmer-Bathroom/dp/B0CB5K34L2
• Casa: https://getcasa.com
• Jimi Hendrix: https://en.wikipedia.org/wiki/Jimi_Hendrix
• Greek Theatre: https://en.wikipedia.org/wiki/Greek_Theatre_(Los_Angeles)
• Pachinko: https://www.amazon.com/Pachinko-National-Book-Award-Finalist/dp/1455563927
• Homegoing: https://www.amazon.com/Homegoing-Yaa-Gyasi/dp/1101971061
• A History of Burning: https://www.amazon.com/History-Burning-Janika-Oza/dp/1538724243
• The Overstory: https://www.amazon.com/Overstory-Novel-Richard-Powers/dp/039335668X
Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
Lenny may be an investor in the companies discussed.