Same Me. A New Chapter.

A new perspective, more practical resources, and a November 3 debut.

Need a hand figuring out AI for your CS team?

The Journey: #86 That's Not My Job Anymore

Every job description for a CSM I read right now still says the same things it said five years ago. Manage the relationship, drive adoption and own the renewal. Meanwhile the actual job has rewritten itself underneath the title without telling anyone, and most of the CS community is still catching up. There's so much fear and noise about AI in this space that people are sprinting to say "we use AI" without ever asking what that should actually mean. I found out the hard way, with a client, in a room, with a whiteboard that got very messy very fast.

The Journey: #85 Collaboration or Compliance

Picture the quarterly planning meeting. Sales walks in with the number, the plan, and the list of what everyone else needs to go do. The rest of the room nods, takes notes on their assignments, and calls it cross-functional alignment. I ran that exact meeting at five different companies and told myself every time that it counted as collaboration.

The Journey: #84 We Didn’t Build This For You

Every product team I talk to right now is bragging about velocity. Two-week release cycles, AI writing half the code, feature drops every Friday. Nobody’s asking the question that actually matters, which is whether their customers can use any of it. I found out how badly that question gets skipped two weeks ago, sitting in a client’s office, staring at a health score that had fallen off a cliff for reasons nobody could explain yet.

The Journey: #83 You Made the Sale, But Not the Money

Every CS org has a number they love to report. Expansion revenue closed, retention rate holding steady or just NRR. Almost none of them report the number that actually determines whether any of it mattered, which is how long it took to stop losing money on the customer they just signed. I didn't know that number existed for the first several years of my career. Then my CFO showed it to me, and it rearranged how I thought about my job.

The Journey: #82 Competitors Don't Need Permission

Think about the last five renewals that closed clean. Not the ones that slipped, not the ones that went sideways, the ones that just renewed, no drama, nothing to see here. Now ask yourself honestly, do you actually know if your customer looked at anyone else first, or did you just assume the relationship was strong enough that it didn't matter. Most of you don't know. And that gap, the space between what you assume and what's actually true, is where you're losing more than you think.

The Journey: #81 I Quit

I've left five companies in my career, and if you'd asked me in the moment, I would have told you all five decisions felt completely different. One felt like growth. One felt like a mistake I was correcting. One felt like survival. One felt like peace. And one felt like heartbreak. People ask me constantly whether they should leave their job, like there's a universal answer sitting somewhere I'm just refusing to hand over. There isn't. But there is a pattern underneath all five of my exits, and I think it's worth pulling apart.

The Journey: #80 Delegation Is Not a Skills Problem

I built my entire CS career on being the person who knew more than anyone else in the room. I was a customer of the product before I ever worked for the company, which meant by the time I was a CSM, I wasn't learning the platform, I was already fluent in it. That fluency became my identity. And it became the exact thing that made me a terrible new leader, because the moment I had a team, the thing that made me great became the thing that made me dangerous.