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Technical Due Diligence

Technical Due Diligence

I tell buyers what they're buying.

I do technical diligence for PE firms, growth investors, independent sponsors, and searchers once they’re under LOI or term sheet on a software, data, or technology-enabled business. The read also tests whether your thesis survives AI over the hold. I’ve led engineering teams for 19 years, and I’ve been on the buy side myself.

I do technical diligence for PE firms, growth investors, independent sponsors, and searchers once they’re under LOI or term sheet on a software, data, or technology-enabled business. The read also tests whether your thesis survives AI over the hold. I’ve led engineering teams for 19 years, and I’ve been on the buy side myself.

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Jason Nappier

What the diligence answers

Six questions, answered before you sign

I examine the team and the technology, including the architecture, code, cloud infrastructure, security, data, and third-party licensing, to answer the six questions that matter to the deal.

01

Whether the thesis survives AI

I assess how AI could weaken the product or the business model over the hold, including where it's automating work the target gets paid for. Most diligence reads don't ask this question explicitly.

01

Whether the thesis survives AI

I assess how AI could weaken the product or the business model over the hold, including where it's automating work the target gets paid for. Most diligence reads don't ask this question explicitly.

01

Whether the thesis survives AI

I assess how AI could weaken the product or the business model over the hold, including where it's automating work the target gets paid for. Most diligence reads don't ask this question explicitly.

02

What changes the price

I size technical debt, deferred maintenance, and key-person dependency so they show up in the model rather than as a surprise after close.

02

What changes the price

I size technical debt, deferred maintenance, and key-person dependency so they show up in the model rather than as a surprise after close.

02

What changes the price

I size technical debt, deferred maintenance, and key-person dependency so they show up in the model rather than as a surprise after close.

03

Whether it runs without the people who built it

In founder-led or thinly staffed businesses, critical technical knowledge often sits with one or two people. I find out what only they know and what it takes to transfer it.

03

Whether it runs without the people who built it

In founder-led or thinly staffed businesses, critical technical knowledge often sits with one or two people. I find out what only they know and what it takes to transfer it.

03

Whether it runs without the people who built it

In founder-led or thinly staffed businesses, critical technical knowledge often sits with one or two people. I find out what only they know and what it takes to transfer it.

04

What it costs over the hold

I estimate the cost of hosting, licenses, replacing end-of-life frameworks, and the engineering hires the plan quietly assumes. You get the number before it becomes your number.

04

What it costs over the hold

I estimate the cost of hosting, licenses, replacing end-of-life frameworks, and the engineering hires the plan quietly assumes. You get the number before it becomes your number.

04

What it costs over the hold

I estimate the cost of hosting, licenses, replacing end-of-life frameworks, and the engineering hires the plan quietly assumes. You get the number before it becomes your number.

05

Whether you’ll own what you’re buying

I check who holds the code, accounts, and credentials, whether contractors assigned their IP, and what exposure sits in open-source and third-party licenses. Issues that need a legal call go to your counsel as a prioritized list.

05

Whether you’ll own what you’re buying

I check who holds the code, accounts, and credentials, whether contractors assigned their IP, and what exposure sits in open-source and third-party licenses. Issues that need a legal call go to your counsel as a prioritized list.

05

Whether you’ll own what you’re buying

I check who holds the code, accounts, and credentials, whether contractors assigned their IP, and what exposure sits in open-source and third-party licenses. Issues that need a legal call go to your counsel as a prioritized list.

06

Whether the plan can be built

When the investment case depends on new development, I assess whether the plan is feasible with the proposed team, budget, and timeline, and set kill criteria, meaning the observable conditions that should stop or change the build.

06

Whether the plan can be built

When the investment case depends on new development, I assess whether the plan is feasible with the proposed team, budget, and timeline, and set kill criteria, meaning the observable conditions that should stop or change the build.

06

Whether the plan can be built

When the investment case depends on new development, I assess whether the plan is feasible with the proposed team, budget, and timeline, and set kill criteria, meaning the observable conditions that should stop or change the build.

How I help

During diligence and after the close

Two engagements, each scoped and priced on its own.

Technical Due Diligence

For PE firms, growth investors, independent sponsors, and searchers acquiring or investing in a software, data, or technology-enabled business. I read the code, work read-only inside the cloud environments, and sit with the people who built and run the systems. You get the findings ranked by what they should change about price, terms, the post-close plan, or the decision to proceed, in a one-page decision view backed by a detailed findings memo. It's a fixed fee, scoped before we start.

Book a Call

Technical Due Diligence

For PE firms, growth investors, independent sponsors, and searchers acquiring or investing in a software, data, or technology-enabled business. I read the code, work read-only inside the cloud environments, and sit with the people who built and run the systems. You get the findings ranked by what they should change about price, terms, the post-close plan, or the decision to proceed, in a one-page decision view backed by a detailed findings memo. It's a fixed fee, scoped before we start.

Book a Call

Post-Close Technology Execution

For acquirers in the first hundred days. The diligence report tells you what to fix, and this is fixing it: stabilizing the technical team, closing the key-person gaps, and putting AI to work where the value creation plan needs it, with the same person who wrote the read.

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Post-Close Technology Execution

For acquirers in the first hundred days. The diligence report tells you what to fix, and this is fixing it: stabilizing the technical team, closing the key-person gaps, and putting AI to work where the value creation plan needs it, with the same person who wrote the read.

Book a Call

By the numbers

A track record you can stand on

19

Years leading engineering teams

40+

Engineers in organizations I’ve scaled

$1B+

Annual revenue through a design tool my teams built

2

Software companies co-founded

Jason Nappier

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Some of the biggest technical risks in a deal come from people, structure, and leadership problems wearing a technical disguise. Reading the code alone won’t find them.

I’ve spent 19 years building and leading the teams that ship software, including hiring, organizing, coaching, and running engineering across companies and continents. Most recently I led 22 engineers and managers across three teams at 8am, a PE-backed legal tech company. Before that I led engineering at Big Health on FDA-regulated, HIPAA-governed digital therapeutics. Earlier I managed an engineering team at Vistaprint and owned the architecture of a security monitoring product at Tenable Network Security.

I’ve also run my own acquisition search and taken a deal through diligence. That taught me what a technical read has to do for a buyer, which is a different job from what it does for an engineer. It has to feed the model, surface what changes the price, and answer whether the business can be run after close.

In most deals, a few issues matter far more to the price and the plan than the rest, so I find those and tell you which to act on first. I’m there after close if you want the same person executing what the read found.

Track record

Nineteen years leading engineering teams, and time on the buy side

Led 22 engineers and managers across three teams at 8am, a PE-backed legal tech company.

Ran my own acquisition search and took a deal through diligence.

Scaled an engineering organization from 15 to more than 30, including building an offshore engineering operation that actually worked.

Led development of the design tool at Vistaprint that more than $1B in annual revenue flows through.

Ran a controlled A/B test measuring the productivity and quality effect of AI-assisted development, then built the enablement and standards that made the gains stick.

Co-founded two software companies. Master’s and Bachelor’s in Computer Science. Trained career and leadership coach.

Questions

Frequently Asked Questions

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Get in touch

Get in touch

What do you need to know before you sign?

What do you need to know before you sign?

A short call

Tell me where the deal stands and what you need answered.

A short call

Tell me where the deal stands and what you need answered.

An honest read

I'll tell you whether I can answer it inside your timeline. If I can't, I'll say so.

An honest read

I'll tell you whether I can answer it inside your timeline. If I can't, I'll say so.

A clear next step

If I can help, I'll tell you the scope, the access I need, and what you'll get.

A clear next step

If I can help, I'll tell you the scope, the access I need, and what you'll get.