Who I Am

I built and sold Launchable (AI/ML for DevOps) to CloudBees after raising from Battery Ventures, Unusual Ventures, and 645 Ventures. Before that, I scaled Jenkins and Bitbucket at CloudBees and Atlassian.

I’m also the author of Dog Inspired: The Art of Embracing Life’s Journey.


What This Newsletter Is About

This isn’t another AI hype newsletter. It’s field notes from actually building, selling, and exiting an AI B2B company.

I write about:

  1. Product & Engineering: Agent engineering, AI-native product development, technical architecture decisions that matter

  2. Go-to-Market: What actually works when selling AI to enterprises (vs. the demo-to-deployment gap everyone ignores)

  3. Building in Public: Real-time lessons from operating AI companies—wins, failures, and everything in between

My rule: If I haven’t done it, seen it work firsthand, or find it fascinating enough to dig into deeply—I don’t write about it.


Who This Is For

Founders, product leaders, and operators building AI-native B2B companies.

Not analysts. Not people watching from the sidelines.

If you’re in the arena—building product, closing deals, managing teams—this is for you.


What You Get

Free subscribers receive weekly posts on building and scaling AI-native B2B companies.

Paid subscribers ($10/month or $100/year) get:

  • All archived content

  • Early access to new frameworks and playbooks

  • Comment access and community discussion

  • Invitations to live operator sessions (coming soon)

Many readers expense subscriptions from L&D budgets.


Posting Schedule

New posts every week. I take 2-4 weeks off per year to recharge and write better content.


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Subscribe to The Operator's Guide to AI-Native B2B — by Harpreet Singh

Operator insights on building AI-native B2B—agent engineering, product, and GTM. Building in public.

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