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Editorial Note by Jordan Wolf: We recently reviewed an excellent, highly critical breakdown of the "AI-native sales organization" model popularized by companies like Anthropic. Having spent years architecting go-to-market systems and managing enterprise revenue operations, the structural risks highlighted in this analysis resonate deeply with my own hands-on experience. Below is our comprehensive review and strategic endorsement of why absolute automation is a dangerous trap

I started working on internet and technology companies starting in 2006. (This doesn’t include my building websites, prototypes, etc… since childhood). My high interest in the SaaS business model started in 2009 in a mixed Undergrad/MBA class at the University of Wisconsin School of Business called Entrepreneurial Finance, where my final project was to do the work of an Investment Banking team preparing a client for their IPO roadshow. That client was pre-IPO OpenTable. Afte

This post was originally posted on my LinkedIn profile blog in 2014 with the title: If I Were 22: Think Smaller. I thought about it recently, re-read it, and decided the message is still great for Founders working on their GTM Strategy. Whether you're working on your first Minimal Viable Product (MVP), working toward Product-Market Fit, or scaling B2B startups I recommend the quick read. --- A close entrepreneur friend of mine once told me his advice for getting started in.

For the past few years, I’ve spent time each day using the popular LLMs to better understand their potential. Given that I’m doing Go-to-Market consulting, I thought it would be fun to upload my resume and seek its hopefully objective assessment. I’ve decided to share the results below. Prompt: “Can you make a summary of my skills and how you think I compare to the market for talent in those skills?” Response: Executive Summary of Your Skill Set 1) Go-to-Market & Revenue Lea