Take the customer breakage now at 100 customers rather than at 300 - but run it through Ryan and sales before it ships

September 23, 2026 at 3:51 PMstrategyhigh

Situation

Pushing Justin Haynes and Nathan Blackham on getting three to five times the throughput out of their orgs, Peter asked where the big blocks of time are. Justin said he could do something immediately that would dramatically speed things up but would break some customers. Peter answer: do you want to break customers now when we have 100 customers, or break customers in a year when we have 300? He then attached a condition - everyone sits down, Justin explains what he wants to change and what the fallout looks like, Ryan Smith and sales both understand it, and then it goes. He pre-warned Ryan in their 1:1 that this is coming.

Reasoning

The disruption is not avoidable, only schedulable, and its cost scales with the installed base - so the cheapest moment to pay it is the earliest. Delay is not neutral here, it is compounding. The condition he attached is the other half: the thing that makes a deliberate breakage survivable is that Support and sales are not surprised by it, which converts a customer incident into a planned migration. He is buying speed with a cost he is willing to name, not pretending the cost is zero.

Additional Context

Emerged from a full day with Justin and Nathan at Peter house on 9/17 planning Linux work and org changes. Peter framed the throughput target as three to five times, explicitly rejecting slow acceleration as a route there.

Observed Evidence

Direct quote of Peter own framing in the Ryan 1:1, corroborated by his description of the same 9/17 session to Steve Wallace the same morning.

Matching Patterns

58%
Time Over Cost(prices the delay before pricing the disruption, treats schedule as the scarce quantity)
52%
Conscious Tech Debt for Execution Speed(accepts a named cost to buy speed, surfaces it to the org rather than absorbing it quietly)

Confidence Breakdown

33/35
Evidence
24/30
Pattern
19/20
Source
12/15
Corroboration

Reasoning Depth Analysis

Org Signal:Breaking a customer is an allowable cost when it is chosen, sequenced and socialised - what is not allowable is doing it by accident, which is exactly what just happened with Veeam.
Who Affected:Ryan Smith and Support absorb the tickets; sales absorbs the customer conversations; Justin org gets the throughput.
Precedent:Establishes that scaling pain is paid forward, and that the gate on deliberate breakage is cross-functional awareness rather than executive approval.
Consequences:Real - Peter told Ryan directly that some stuff is going to come, so the change is expected to ship.
Timing:Now rather than later is the entire content of the decision; 100 versus 300 customers is the stated clock.

Source

reflection

AI Confidence

88%

Related Context

🎥
Ryan <> Peter Weekly 1:1, 2026-09-18

fathom

Justin is like, well, I can do something right now that is going to dramatically speed things up, but I am going to break some customers if I do it. My response to him was, okay, well, do you want to break customers now when we have 100 customers, or do you want to break customers in a year when we have 300 customers? Let us all get together. Let us understand what you want to change. Let us make sure Ryan understands what you want to change, what the fallout is going to look like for some customers. Let us make sure that sales understands. And let us go do it. And then let us go faster.

🎥
Steve <> Peter Weekly 1:1, 2026-09-18

fathom

I had Nathan and Justin here for the day yesterday. What processes we can change to get five times the throughput. I am going to make some changes there.

Outcome

No outcome recorded yet.

Decision ID: f95d9932-1472-4ba7-bda3-6256ce36e99c