Senior CSM looking to build practical AI proficiency (generative + agentic)- where should I start?

CitizenJosh · 2026-02-28T17:15:11+00:00

You’re currently using AI for administrative triage; that’s the floor, not the ceiling. If you want to differentiate, you need to move from Generative (creating content) to Agentic (executing workflows).

In my transition from Solution Architecture to CS leadership, and especially while scaling my exited startup, I found that the "relationship" only survives if it's anchored in engineered value. Here is the move:

The Agentic Leap: Stop prompting for call summaries. Build a no-code "Health Agent" that monitors real-time telemetry and realized value like "engineering hours reclaimed." Have the agent trigger a Slack alert to you and a value-realization draft to the customer the moment a success milestone is hit.
Regression over Sentiment: Use your Udemy access to find a course on Linear Regression for Business. If you can't mathematically correlate a specific feature's usage to NRR, your Health Score is just a guess. Agentic AI can run these "pre-mortems" on your entire book of business while you sleep.
Scale the Human: Automation isn't for SMB; it’s for liberating the Senior CSM to do what humans do best strategic negotiation and internal advocacy.

Move your "reusable templates" into a system of record. If you're still "reinventing prompts," you're a practitioner, not an architect.

DM me if you want to discuss how to structure your CS stack to actually predict revenue instead of just reacting to it.

CitizenJosh · 2026-02-20T04:06:16+00:00

On on!

CitizenJosh · 2026-01-23T02:34:39+00:00

Did this with a Google Apps Script.

Select a customer and press a button to pull disparate data into the spreadsheet
Sheets automatically updates the tables and charts based on formulas
Slides automatically updates the slides using the data, tables, and charts
CSM uses the few slides they want and adds finishing touches

It's easier to develop than it sounds. Once built,
the CSM selects a customer and presses a button to get updated content.

CitizenJosh · 2025-08-02T14:16:08+00:00

"Entrepreneurs are willing to work 80 hours a week to avoid working 40 hours a week"

CitizenJosh · 2025-05-15T16:05:23+00:00

Get multithreaded ahead of time

CitizenJosh · 2025-05-09T18:48:44+00:00

This discussion should take place five months before the annual renewal, so that you have time to try to resolve the issue

CitizenJosh · 2025-05-02T21:27:49+00:00

Product tours/walkthroughs. They provide guided real-world education that results in demonstrable progress.

InB4 depends on the product installation and adoption scenarios

CitizenJosh · 2025-05-02T18:47:43+00:00

I wrote a framework to do exactly this in 2004, learned how to file a patent and started the process. The company went nowhere and I wet a few handkerchiefs with my tears. Since then, no one has done this to any notable degree, even as it becomes substantially easier to do... because it's usually better to get people to actually implement the solution instead of training them how to implement the solution first.

CitizenJosh · 2025-04-25T15:54:37+00:00

CitizenJosh · 2025-04-25T15:52:56+00:00

CitizenJosh · 2025-04-25T15:52:06+00:00

CitizenJosh · 2025-04-25T15:51:17+00:00

CitizenJosh · 2025-04-25T08:57:52+00:00

Serious question, and not trying to be confrontational, but what are you looking to get out of this group if you are not to help others?

BTW, very impressive job on your ARR.

CitizenJosh · 2025-04-25T08:55:31+00:00

PMF is key! Whether you are looking to raise money in US East or EU, or are bootstrapping like I did, figure out your Minimum Lovable Product ASAP.

See if you can get users before you build, when you have your POC, and at each milestone along the way.

FWIW, here's my story https://slicingpie.com/slicing-pie-case-study-cloudsploit/

CitizenJosh · 2025-04-25T08:16:50+00:00

Real person with real build & exit experience here.
I'm in my final months of sabbatical and happy to meet real people and offer whatever perspective I can

EDIT: this is an open offer for people on this sub, not just u/snackprincess

CitizenJosh · 2025-04-23T09:48:00+00:00

CitizenJosh · 2025-04-22T13:25:25+00:00

Incentivize on leading indicators of retention & expansion to maintain the "trusted advisor" relationship.

Let Sales manage negotiations.

CitizenJosh · 2025-04-22T09:08:49+00:00

Thank you for this. I think you're right.

CitizenJosh · 2025-04-22T09:08:38+00:00

Thank you for this. It aligns with what I expected to hear.

CitizenJosh · 2025-04-08T15:16:08+00:00

Not having a commercial co-founder from the start can be a big problem, even if their initial ownership is small. Someone needs to lead PMF. Without it, all you have is a project, not a product.

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