Your product can threaten your product

Product-market fit is not a finish line you cross once and then frame on the wall. Markets move. Customers change. The thing that got you here frequently becomes the thing that keeps you here.

There are a few ways this happens.

One large customer gets loud enough that the roadmap starts bending around them (and they take a permanent seat on your shoulder). A feature ships for one account, then stays forever because nobody wants to have the cancellation conversation. An experiment becomes permanent furniture. The team keeps maintaining things that no longer earn their place.

That is how product debt accumulates. Not because anybody is careless, but because every local decision can sound reasonable while the whole product drifts away from the customers you actually want to serve.

At SalesLoft, we used to say "Customers First." The distinction matters: CustomerS first, not Customer first. One customer can be wrong. A pattern across the right customers should be ignored at your peril.

You absolutely should not reject every big opportunity or pretend every customer is interchangeable. Instead, recognize when revenue is buying a product decision that will make the next ten deals harder.

Read the full article "Your Product Threatens Your Product" here: https://huntersoftwareconsulting.com/posts/2026-08-30-product-threatens-product/

Aly Madhavji joined me for a conversation about fundraising readiness, and he put one part of the process very plainly: a pitch deck has never raised money.

The deck has a job. It gets you a meeting.

After that, the failure mode moves. If nobody takes the meeting, inspect the short message and the hook. If investors take the meeting but disappear during follow-up, the deck may not be the problem anymore. Look at the pitch, the follow-up, and whether you are showing progress over time.

Aly also recommends having an 11-second pitch, a 30-second pitch, and a 90-second pitch. That is useful because founders often try to make one artifact do every job. A sentence that earns attention is not the same thing as a conversation that builds confidence, and neither is the same thing as a data room that makes diligence easy.

The episode is live on YouTube: https://www.youtube.com/watch?v=h2_ldHhY8RQ&pp=0gcJCRMMAYcqIYzv

This Friday, ask:

The point is not to turn the founder into a part-time engineer. It is to make the business legible enough that the founder can make the calls that they have to make.

If the answers are fuzzy, do not immediately request more metrics. Find the missing owner, give them the data and ownership to get you clarity. The right human can always cut through a system's noise.

Anthropic's Claude in Chrome is now generally available. It can read, type, navigate, click, and fill forms using existing logins.

That matters because the AI conversation has moved from "Can it help me with this?" to "Can it do this for me?"

If an agent changes a CRM record, sends a message, submits a vendor request, or updates a customer account, the action still needs a DRI - Directly Responsible Individual. Before putting one of these workflows into production, decide how to reverse the action, when a person reviews it, and which system is your source of truth.

I like the capability, and use it regularly. I do not want the capability making the operating decisions for me.

The company can look busy while the business remains enmired. Tickets move. Meetings happen. Code reaches production. Meanwhile, the founder has less time to sell, the team cannot explain what's changing, and the product drifts toward whoever shouted last (or what an agent last suggested).

The work is not to make the system busier. It is to make the connection between work and business outcome visible enough to act on.

Don't let perfect become the enemy of good - just make progress. See you next week.

- Hunter