Pre-Sale Technology & Data Advisory

Trigpoint
Advisory

Clear vision. Before the deal.

If you're thinking about selling your business in the next one to three years, your technology and data will either add real value to the deal — or quietly undermine it.

Most owners only find out which one it is when a buyer's due diligence team starts asking awkward questions.

I work with businesses on short, cost-effective pre-sale technology and data reviews — typically 5 to 10 days over 4 to 6 weeks. The result is a practical, plain-English guide to what will genuinely improve your sale, what to stop spending money on, and what a buyer's team is likely to find before you do.

Have a conversation

Value created for businesses

80%+
faster insight and reporting — giving leadership teams better information, faster
50%+
reduction in manual effort through AI and automation
30%+
cost reduction through targeted simplification
£2m+
in direct savings delivered across complex, regulated businesses
Lowerrisk
reduced exposure through adoption of basic data privacy policies — one of the most common buyer objections, and one of the cheapest to fix
Lowercost
reduced technology spend through supplier simplification — cutting what isn't earning its keep before a buyer uses it against you

The problem

Technology and data issues are one of the most common reasons deals go wrong — or go for less than they should.

Most business owners don't see it coming. By the time a buyer's team raises a flag, there's nothing you can do about it cleanly. The time to act is before the process starts.

01

Technology that's become a liability rather than an asset — and the owner doesn't know which it is

02

Data practices that won't survive scrutiny — GDPR gaps, inconsistent reporting, weak controls

03

Spending on systems that aren't earning their keep and won't impress a buyer

04

Missed AI and automation opportunities that could have strengthened your numbers before going to market

05

No clear, credible technology story to tell buyers — and no one to help you build one

06

The noise around AI is deafening — and most businesses don't know where to start, what's real, or whether their data is in good enough shape to get any value from it at all

"No jargon. No 200-page reports. No expensive team of consultants. Just clear, experienced advice — focused entirely on what matters for your sale."
James May · Trigpoint Advisory

How it works

A short, focused engagement. Minimal disruption. Clear output.

01

An honest conversation first

No obligation. We talk about where your business is heading and whether this is the right moment to take stock of your technology and data position.

02

A short, focused review

Typically 5 to 10 days over 4 to 6 weeks. I work across your teams — from leadership to the people doing the day-to-day work — without disrupting the business. The real picture is rarely found at the top.

See how a typical engagement runs →
03

Regular updates throughout

No surprises. You know what's emerging as we go. Nothing lands in a final report that you haven't already heard about.

04

Clear, plain-English output

A practical guide — not a 200-page report. Three clear sections: what to start or continue doing, what to stop, and what needs more thought before you decide. Written for a business owner, not a technical team.

05

Introductions and ongoing support

If changes need making, I can introduce you to trusted technology and data providers. And if you want a steady hand through the sale process itself, ongoing advisory support is available — a few days a month, as and when you need it.

What you walk away with

  • ✓
    A clear view of the 2–5 things that will genuinely move the needle on your valuation
  • ✓
    Fewer unpleasant surprises when a buyer's team starts digging
  • ✓
    Confidence you're not spending money on changes that won't matter to a buyer
  • ✓
    An honest view of what to stop doing — and what's just noise
  • ✓
    A technology and data narrative that holds up under scrutiny
  • ✓
    Introductions to trusted providers if changes need making

The output — at a glance

Start or continue
What will improve valuation
Quick wins with EBITDA impact
Changes to make before market
Stop or don't start
Spend that won't move the needle
Projects that create noise
Technology costing more than it earns
Consider further
Areas needing specialist input
Decisions that depend on buyer type
Risks to monitor, not necessarily fix

Experience

25 years working in technology. At every level — from the boardroom to the shop floor.

I started as a developer and have spent 25 years working my way through technology teams, then running them, then advising boards. I've worked across professional services, financial services, legal, e-commerce, and manufacturing — in businesses ranging from small owner-managed firms to a FTSE 100 company with over a million clients.

What makes the difference isn't seniority — it's range. The people who know where the real problems are buried are often not in the boardroom. Some of the most valuable conversations I have are with operations managers, finance teams, and front-line staff who've been quietly working around a broken system for years. I know how to have those conversations — and how to turn what I hear into something that matters commercially.

2022 – 2026

Chief Data Officer

FTSE 100 Financial Services Business

Led data, technology and AI strategy across a large, regulated business with over a million clients. Advised the board on where to invest — and, just as importantly, where not to.

2016 – 2022

Director — Technology & Transformation

Large-scale investment platform

Led all technology across a complex platform. Cut the cost base by over 30% through targeted simplification — without cutting capability.

2013 – 2016

Head of Division — Technology Services

Financial services

Built and led development, UX, testing and release management. Introduced DevOps and managed offshore delivery.

2008 – 2013

Head of IT

Mewburn Ellis LLP — specialist IP law firm

2004 – 2008

Head of IT Services & Project Management

Bond Pearce LLP — regional law firm

1999 – 2004

Developer & IT Service Manager

Apex Computers (IBM Partner)

Ongoing

Non-Executive Director

Stephenson Law

Advisory role connecting technology decisions to commercial outcomes.

What this has delivered in practice

80%+
faster insight & reporting
50%+
effort saved through automation
30%+
cost reduction delivered
£2m+
in direct savings

These aren't aspirational figures. They're the result of making the right calls about where to invest, what to simplify, and what to stop doing — across businesses of very different sizes and sectors. The same thinking applies whether you're running a £3m professional services firm or a much larger, more complex operation.

How a review runs

What happens — and when.

A typical Trigpoint review takes 5 to 10 days of actual work, spread across 4 to 6 weeks. Here's what that looks like in practice.

Before
we start

The initial conversation

A straightforward chat
No forms, no pitch decks. We talk about your business, your sale timeline, and what's keeping you up at night. I'll tell you honestly whether a review makes sense — and if so, what it would involve.
Scoping and access
We agree who I'll need to speak to, what documents to pull together, and how to keep disruption to an absolute minimum. A short survey goes out before week one begins.
Week 1

Surveys, documents and first conversations

Structured surveys
Short, targeted surveys go to the right people — leadership, finance, operations, IT, and a handful of front-line staff. 10 to 15 minutes each. No jargon.
Document requests
Technology spend, software licences, IT asset register, sample MI reports, backup records, GDPR policies — whatever exists. Nothing elaborate required.
First interviews
60-minute conversation with the owner or CEO. 45 minutes with the finance lead. These set the commercial context before the detailed work begins.
Weeks
2 – 3

Deeper conversations and operational observation

Operational interviews
Conversations with the IT or tech lead, operations manager, and HR. These are where the real picture emerges — the systems held together with workarounds, the manual processes nobody talks about, the key-person risks that wouldn't be obvious from the top.
Observation and walkthrough
Where useful, I'll walk through a typical working day in the key systems — not to audit the code, but to see what people actually do and where the friction is. Front-line staff often hold the most valuable insight.
Why this matters: The things that catch businesses out in due diligence are rarely what the leadership team is worried about. They're the things nobody thought to mention — because they've always worked that way.
Weeks
3 – 4

Analysis and first-draft output

Everything pulled together
Survey responses, interview notes, documents and observations are cross-referenced against a structured review framework — covering policy, governance, technology, process, people, and commercial impact.
Commercial judgement applied
AI helps organise and structure the initial output. But 25 years of experience is what decides what actually matters — what to prioritise, what a buyer will care about, and how to frame it in a way that's useful to you, not just accurate.
Weeks
4 – 6

Output delivered and next steps agreed

The plain-English summary
What to start, what to stop, what to consider further. Written for you and your advisers — not a technical audience.
Walkthrough conversation
We go through the findings together. No surprises — you've had updates throughout. This is where we agree what to prioritise and in what order.
Introductions if needed
If changes need making, I'll introduce you to the right people — without you having to navigate the technology market on your own.

What a Trigpoint review covers

The same ground a buyer's team will cover — months before they arrive.

A buyer's due diligence team will examine every area below in forensic detail. A Trigpoint review covers the same ground at a high level — so you know what's coming, what to fix, and what it means for your deal. No nasty surprises. No running out of time to act.

DD Buyer's full due diligence — deep, forensic, specialist
SL Trigpoint review — high-level, directional assessment
→ Flagged to relevant advisers
— Not in scope for either
Policy & Compliance
GDPR & data protection
✓
Full DD — forensic review
✓
Trigpoint — gaps flagged
If not addressed deal risk
Gaps found in DD give buyers grounds to renegotiate price or delay completion. Serious breaches carry fines of up to £17.5m.
Benefit of acting early
Policy fixes cost almost nothing and remove one of the most common buyer objections before it becomes leverage against you.
Cyber security posture
✓
Full DD — inc. pen testing
✓
Trigpoint — exposure flagged
If not addressed deal risk
A breach during the sale process can collapse a deal entirely. Buyers increasingly require Cyber Essentials or equivalent as a condition.
Benefit of acting early
Knowing your exposure means you can address the worst of it cheaply — before a buyer's team does it for you.
Software licensing
✓
Full DD — full audit
✓
Trigpoint — risks identified
If not addressed deal risk
Unlicensed software creates legal liability that transfers to the buyer — a reliable, low-effort way for them to reduce the price.
Benefit of acting early
Inexpensive to fix and closes a clean line of attack on your valuation.
Governance & Ownership
Key person dependencies
✓
Full DD — team interviews
✓
Trigpoint — identified & mitigation advised
If not addressed deal risk
If the business runs on one person's knowledge, buyers price in the risk — or make their retention a condition of the deal.
Benefit of acting early
Documentation and cross-training reduce this visibly and cheaply before DD exposes it as a structural weakness.
Technology spend review
—
Full DD — not in scope
✓
Trigpoint — waste identified & costed
If not addressed quick win
Unnecessary spend suppresses EBITDA quietly. Buyers who spot it use it to argue the business is poorly managed.
Benefit of acting early
Cutting £20–80k of wasted annual spend improves EBITDA directly. At a 5–10x deal multiple, that's £100k–800k added to your sale price.
IP ownership & software contracts
✓
Full DD — legal review
→
Trigpoint — flagged to legal advisers
If not addressed deal risk
Custom software with no clear ownership creates unresolved liability — a common problem that surprises owners.
Benefit of acting early
Identified early so legal advisers can resolve it — not surfaced in DD as an open issue with no resolution ready.
Technology & Systems
Core systems landscape
✓
Full DD — detailed review
✓
Trigpoint — mapped & risks flagged
If not addressed
Buyers form their own view of your systems — often worse than reality. Fragmented systems signal operational risk and inflate their cost estimates.
Benefit of acting early
A clear map with an honest narrative puts you in control of the conversation — rather than reacting to a buyer's assumptions.
Legacy or unsupported systems
✓
Full DD — detailed review
✓
Trigpoint — commercial impact assessed
If not addressed deal risk
Buyers identify replacement costs and deduct them from the price — typically more than the actual cost of replacement.
Benefit of acting early
Real cost estimates in hand mean you frame this as a known, managed issue — not a surprise that hands negotiating power to the buyer.
AI & automation opportunities
—
Full DD — not in scope
✓
Trigpoint — opportunities mapped & costed
If not addressed value add
Efficiency gains that could have improved EBITDA before sale are left on the table — and the benefit goes to the buyer, not you.
Benefit of acting early
Even simple automation — reporting, onboarding, reconciliation — can save £50k+ annually. At a 5–10x multiple, that's real money added to your sale price.
Process & Operations
Reporting & management information
✓
Full DD — data quality review
✓
Trigpoint — gaps identified
If not addressed common issue
Manual or slow MI raises doubts about whether the numbers can be trusted. Buyers use this to question the whole financial picture.
Benefit of acting early
Automated reporting is often quick to implement using tools already paid for — and immediately strengthens buyer confidence in the data.
Data quality & integrity
✓
Full DD — forensic review
✓
Trigpoint — worst areas flagged
If not addressed deal risk
Inconsistent data undermines confidence in every number the business presents. Buyers use it to discount across the board.
Benefit of acting early
Even basic data clean-up changes the buyer's perception of how well-run the business is — and protects the credibility of your financials.
People & Skills
Technology team capability
✓
Full DD — team assessment
✓
Trigpoint — gaps identified
If not addressed common issue
Capability gaps raise post-acquisition cost in the buyer's model — directly reducing what they're willing to pay.
Benefit of acting early
A clear view of gaps means you can address the most visible ones — or have a credible plan ready rather than leaving it as an open question.
Offshore / contractor dependencies
✓
Full DD — contract review
✓
Trigpoint — exposure flagged
If not addressed deal risk
Contractors without contracts create IP and liability exposure that transfers to the buyer — flagged by every buyer's legal team, every time.
Benefit of acting early
Basic agreements are straightforward to put in place and close a gap that would otherwise be a standard DD finding.
Commercial & Valuation Impact
Technology's impact on EBITDA
—
Full DD — not in scope
✓
Trigpoint — modelled & quantified
If not addressed value add
Technology costs that could be cut, and opportunities that could add value, go unrecognised — and the upside goes to the buyer at your expense.
Benefit of acting early
A £50k EBITDA improvement adds £250k–500k to your sale price at a 5–10x multiple. This is where the review pays for itself many times over.
Deal risk & action plan
✓
Full DD — findings report
✓
Trigpoint — prioritised action plan
If not addressed deal risk
Risks surface in DD when there is no time to fix them — and a buyer has every incentive to use them against you.
Benefit of acting early
The same issues, found 12 months earlier, can almost always be resolved at modest cost. Trigpoint turns what would be a DD report into a to-do list you complete before anyone is watching.

Why now

The market for owner-managed business sales is active. Technology issues are consistently one of the biggest reasons deals go for less — or don't go through at all.

The evidence isn't from theory. It comes from the deals themselves.

7,492
UK M&A deals in 2024 — the highest annual volume since 2018
88%
of UK deals by volume involved SMEs — businesses just like yours
96%
of senior technology leaders say tech due diligence has uncovered major issues in M&A deals
30%
of failed mergers are attributed directly to technology integration issues
⚠️
Issues found in DD are expensive
When a buyer's team finds a problem, you're in the worst possible position to deal with it — under time pressure, with the buyer holding the leverage. The result is price chipping, extended warranties, earn-out dependency, or deals that fall apart altogether.
📋
Most sellers aren't prepared
Technology review — if it happens at all — typically arrives during due diligence, by which point there's no runway to fix anything cleanly. Only one in four business owners conducts any form of technology review before going to market.
✅
The fix is usually simpler than it looks
Most technology issues that surface in DD are fixable — given time. GDPR policies, backup processes, software licences, reporting automation. The same work that costs a few thousand pounds to address before a sale can cost hundreds of thousands in price reductions if found by a buyer's team.
Typical return on investment
10x+
For a business with an enterprise value of £5m, a technology issue that prompts a 5% price reduction costs the seller £250,000. A pre-sale review that enables remediation of that issue typically costs a fraction of that — making it one of the highest-return investments a business owner can make in the run-up to a sale.

Pre-sale technology review isn't a cost of doing business. It's a value-creation activity.

Get in touch

If you're thinking about a sale, let's have an honest conversation.

No commitment required. Just a straightforward chat about where you are, where you're heading, and whether this could help.

Phone07428 700115
Emailjames@trigpointadvisory.co.uk
LinkedInJames May
BasedSouth West England