Technical due diligence, from the seller's side
Most guidance on technical diligence is written for the buyer. I have been on the seller's side of a completed acquisition of a company I wrote the code for. I get founders ready for the review before a sale or a raise, so it confirms the story instead of unravelling it.
Why diligence catches founders out
By the time a buyer's technical team shows up, the deal is supposed to be mostly agreed. What that team finds can still move the price, add earn-out conditions, or end the process. The problem is timing: most of what diligence penalises, a business that lives in one person's head, an architecture nobody wrote down, security work that got deferred for two years, cannot be fixed in the few weeks between a letter of intent and the review.
I have been on the other end of this. I coded one of the first LinkedIn automation platforms myself, grew it to 500+ B2B clients with zero outside funding, built a team of 20, and sold the company in June 2025. The exit is on the record. The founder of Acquire.com interviewed me about it. So I prepare founders for the questions I was actually asked, not a generic checklist.
What a buyer's technical review looks at
Every acquirer and lead investor runs some version of this. The specifics vary; the categories do not.
How I get you ready
The work is not cosmetic. It is making the findings true and boring before a stranger goes looking for them. I help founders reduce founder-dependency, clean up the technical story, and turn the messy parts into a documented list rather than a surprise, so the buyer's reviewer finds exactly what you told them they would.
Concretely: an honest audit of where the technical story is weak; a plan to reduce the bus factor and write down the architecture; the obvious security and IP gaps closed; and a data room that answers the predictable questions before they are asked. When the review comes, it becomes a formality instead of a negotiation you are losing.
This is one strand of fractional CTO work. If you are not selling yet but want the option open, the same preparation is just good technical hygiene, and it is far cheaper to build in than to retrofit under a deadline.
When to start
Earlier than feels necessary. Six to eighteen months before you expect to sell or raise is enough time to move founder-dependency and documentation, the two things that cannot be crammed. If you are already in a process, a focused review still pays for itself by finding the issues before the buyer's team does, while you still control how they are framed.
Questions founders ask
What is technical due diligence?
Technical due diligence is the review a buyer or investor runs on your technology before they close a deal. They look at whether the code is maintainable, whether the business can run without any one person, what the security and compliance exposure is, how much technical debt is hiding in the roadmap, and who actually owns the code and the third-party dependencies. The output is a risk assessment that moves the price, changes the deal terms, or kills the deal. Preparing for it in advance is what keeps it from doing the last one.
How do I prepare my startup for technical due diligence?
You reduce founder-dependency so the company is not one person's head, you write down the architecture and the decisions behind it, you close the obvious security and compliance gaps, you make the licensing and IP ownership clean, and you turn the messy parts into a known, documented list rather than a surprise. The goal is that a buyer's technical reviewer finds what you already told them they would find. I sold my own bootstrapped SaaS in 2025, so I prepare founders for the questions I was actually asked, not a generic checklist.
When should I start preparing for technical due diligence?
Before you have a term sheet, ideally six to eighteen months before you expect to sell or raise. Most of what diligence penalises, founder-dependency, undocumented architecture, deferred security work, cannot be fixed in the few weeks between signing a letter of intent and the review. Starting early turns diligence from a scramble into a formality. If you are already in a process, it is still worth a focused review to find the issues before the buyer's team does.
Why hire a fractional CTO for due diligence instead of a consultancy?
Because a consultancy sends you a checklist and a junior team; a fractional CTO who has sold a company sends you the person who has been in the room. I have been on the seller's side of a completed acquisition of a company I wrote the code for myself, so I know which findings actually move a deal and which ones a buyer raises to negotiate. You get one senior operator, a small number of founders at a time, and no agency markup.
What does due diligence readiness cost?
It usually starts with a $295 strategy session: one focused hour plus a written diagnosis of where your technical story is weak and what to fix first. Deeper readiness work runs as ongoing advisory from $995 a month, or a fractional CTO engagement scoped per company, typically a few days a month. The first 30-minute intro call is free, and it is where we decide which of those fits. See full pricing.
Thinking about a sale or a raise?
Tell me where you are and roughly when. The first 30 minutes are free, and you will leave with an honest read on how your technical story holds up.