Fractional CIO | IT Strategy for High-Stakes M&A | Faster M&A, Smoother Exits | De-risking IT & unlocking value | Author

Most technology integrations miss their synergy targets. Not because the technology is wrong, but because the right leadership wasn't in place early enough.

That's where I come in.

I'm an Interim / Fractional CIO specialising in Transformation & Resilience. I work with CEOs and boards of multi-site, acquisition-led businesses, typically PE-backed, 500–10,000 employees, to turn technology from a source of risk into a source of value.

When integration timelines slip, cyber posture is unclear, or the estate has grown faster than the team can manage, I step in to stabilise delivery, simplify complexity, and build a roadmap the board can trust.
Recent engagement:

VetPartners (BC Partners-backed, £1B revenue, 14,000 staff, 9 countries). Built the Group IT Strategy from scratch. Created acquisition integration blueprints. Accelerated new practice onboarding by 30%. Simultaneously ran IT operations for 540 UK practices.

Career outcomes:

£700M+ M&A technology integration across the platform and bolt-on acquisitions
£15M+ annual EBITDA contribution through operational excellence and cost optimisation
Technology leadership across automotive retail, consumer goods, and veterinary services

Clients call me when:

→ Integration is off-track, and synergies are at risk
→ The board wants cyber confidence before exit, audit, or due diligence
→ Technology is a red flag in the data room
→ They need senior leadership fast—without permanent headcount

I also serve as NED (Digital & Technology) at Age UK, and I've published on AI governance, IT leadership, and board-level technology strategy.

Available for select interim and fractional mandates.

Let's talk: DJ@Starkhorn.co.uk

Daniel J. Jacobs

The AI didn’t fail. It did exactly what we asked, just not what we meant.
We built an agent that ran flawlessly… until everything around it started quietly breaking.

 If you're leading AI deployments or planning to, this reflection might save you some heartache.

👇 Read it here: Reflections on Agentic AI, Human Trust, and the Space 

Between Promise and Reality

What’s the most surprising thing you’ve learned deploying AI in the real world?

Interim / Fractional CIO (Transformation & Resilience) | Board-level clarity on Technology (Risk • Cost • Delivery) | Multi-site & acquisition-led businesses | M&A integration • Cyber resilience • Operating model

View newsletter: Digital Disruption Digest

The system did what we asked. It just didn’t do what we meant, and we didn’t realise the difference until something subtle broke. Reflections on Agent

Open article: The AI didn’t fail. It did exactly what we asked — just not what we meant. by Daniel J. Jacobs • 7 min read

The AI didn’t fail. It did exactly what we asked — just not what we meant.

“We won’t fix the legacy stack, it’s too complex and too expensive. Let’s add AI and show progress.”

That move can create a short-term win.

The short-term gain

➡️ Nicer dashboards and “insight” layers
➡️ A quick story for the board: “We’re doing AI”
➡️ Lower upfront disruption than a proper rebuild
➡️ Faster cycle times in a few workflows (support, sales ops, reporting)

It feels like momentum because some metrics will move.

𝐓𝐡𝐞 𝐥𝐨𝐧𝐠𝐞𝐫-𝐭𝐞𝐫𝐦 𝐜𝐨𝐬𝐭 (𝐭𝐡𝐚𝐭 𝐪𝐮𝐢𝐞𝐭𝐥𝐲 𝐞𝐚𝐭𝐬 𝐭𝐡𝐞 𝐛𝐞𝐧𝐞𝐟𝐢𝐭)

If the core systems are brittle, AI becomes a high-gloss layer sitting on low-trust data and fragile processes.

You end up with:

➡️ Automation of mess (you scale inconsistency, not performance)
➡️ Rising change cost (each “quick win” increases architectural debt)
➡️ Hidden operational risk (every new model relies on unstable integrations)
➡️ A strategy trap (it looks modern, so the real modernisation never happens)
➡️ AI outputs nobody trusts (because the underlying data is wrong or incomplete)

AI on broken foundations doesn’t transform the business; it amplifies whatever the business already is.

𝐀 𝐂𝐄𝐎-𝐥𝐞𝐯𝐞𝐥 𝐰𝐚𝐲 𝐭𝐨 𝐭𝐡𝐢𝐧𝐤 𝐚𝐛𝐨𝐮𝐭 𝐢𝐭

Don’t ask, “Where can we deploy AI?”

Ask, “Where do we have clean ownership, stable data, and a repeatable process so AI can compound value instead of compounding risk?”

𝐑𝐮𝐥𝐞 𝐨𝐟 𝐭𝐡𝐮𝐦𝐛:

If a process can’t be measured, governed, and explained without AI… Adding AI won’t fix it. It will just make it faster and harder to debug.

𝐐𝐮𝐞𝐬𝐭𝐢𝐨𝐧: Where in your business is AI used to modernise, and what would fixing the foundation unlock instead?

Kicking off 2026 with renewed energy and big goals, but what I’m hearing from leadership teams isn’t “new year, new me”.

It’s urgency.

After months of planning in 2025, 2026 is shaping up as the year of decisive execution. The “nice-to-have” transformation work is becoming “must-have” modernisation, and the question has changed:

𝐍𝐨𝐭: “Should we modernise?”
𝐁𝐮𝐭: “How fast can we move without breaking what already works?”

The companies that win this year will treat technology as a strategic lever, not a support function:

➔ IT optimisation as a weapon, not a cost centre
➔ M&A integration as value creation, not operational admin
➔ Cybersecurity as business enablement, not just risk management

If 2026 is the year you’re aiming to reduce complexity, strengthen resilience, or become acquisition-ready, I’m happy to compare notes.

What’s your biggest technology challenge heading into 2026?

#ITStrategy #DigitalTransformation #Cybersecurity #BusinessGrowth #2026Goals

New IT strategy question for 2026:
How fast can you change your mind—without breaking the business?

That confession will sound familiar to anyone who has watched organisations cycle through enthusiasm and quiet disappointment. Project NANDA’s prelimi

Open article: New IT strategy question for 2026:
How fast can you change your mind—without breaking the business? by Daniel J. Jacobs • 7 min read

70% of digital transformations fall short. It's not because the technology fails, but rather because the operating model remains unchanged. (McKinsey/BCG)

After years spent guiding transformations and saving millions across PE-backed businesses, one truth is impossible to ignore:

“Technology rarely breaks a transformation.
Behaviour, capability, and ownership do.”

Because if the organisation doesn’t change how it works, the tooling becomes nothing more than expensive wallpaper.

Here’s how this destroys EBITDA:

𝟏. 𝐁𝐞𝐡𝐚𝐯𝐢𝐨𝐮𝐫𝐚𝐥 𝐅𝐚𝐢𝐥𝐮𝐫𝐞

If leaders don’t change how they work, new systems become old habits wrapped in a new interface.

Commercial impact:
→ £300k–£700k in unrealised value for a mid-market portfolio company.

𝟐. 𝐋𝐚𝐜𝐤 𝐨𝐟 𝐂𝐚𝐩𝐚𝐛𝐢𝐥𝐢𝐭𝐲

You can’t scale with a workforce that doesn’t believe in the new system—or lacks the skills to use it.

The hard truth:

- 60% of work can be automated
- 70% of teams fear the capability gap
- 80% of leaders mistake resistance for stubbornness (instead of upskilling)

Commercial impact:
→ 10–15% rise in operating costs (often £500k+ annually)

𝟑. 𝐙𝐞𝐫𝐨 𝐎𝐰𝐧𝐞𝐫𝐬𝐡𝐢𝐩

When nobody owns decisions, transformations collapse under their own weight:

- No clear accountabilities
- No single owner for platforms
- No clarity on “who delivers what, by when”

Commercial impact:
→ £5M–£10M wiped off the exit valuation due to poor execution discipline

𝐓𝐡𝐞 𝐫𝐮𝐥𝐞 𝐨𝐟 𝐭𝐡𝐮𝐦𝐛:

Spend your first 30 days on:
✓ Shifting behaviour
✓ Upskilling teams and rebuilding capability
✓ Establishing clear ownership and decision rights

When behaviour, capability, and ownership move in tandem, PE-backed companies typically see a 1–4% annual improvement in EBITDA.

Because successful transformations were never about technology —
They’re about disciplined execution.

Repost ♻️ if you’re tired of seeing transformations fail for the same avoidable reasons.

P.S. CIOs, which mistake (1–3) do you see most often in the field?

Early in my career, I measured myself by how much I was needed.

Every escalation that landed on my desk felt like proof I was valuable.
Every decision that required my sign-off confirmed I was essential.

Then I took two weeks off. And the wheels came off.

Not because my team wasn’t capable.
Because I’d built a system that required me to function. I’d confused being needed with being effective.

That was a hard lesson. And it shows up fast in boardrooms and due diligence.

When investors assess a business, they’re not only looking at EBITDA.
They’re quietly asking: what happens if this person leaves?

If the honest answer is “things slow down” or “decisions stall”, that risk gets priced in, even if performance looks fine today.

The harsh reality for technology leaders is that being indispensable isn’t a sign of strength; it's a sign of vulnerability masked as importance.

The shift that changed how I lead:

𝐒𝐭𝐨𝐩 𝐚𝐬𝐤𝐢𝐧𝐠, “How do we perform when I’m here?”
𝐒𝐭𝐚𝐫𝐭 𝐚𝐬𝐤𝐢𝐧𝐠, “How do we perform when I’m not?”

Design decision rights so choices don’t bottleneck.
Build operating rhythms that run without you in the room.
Create clarity so your team doesn’t need to check with you; they already know.

That’s operational maturity: not a leader holding things together, but a system that doesn’t need holding.

What’s one thing you’ve deliberately built to work without you?

PE firms don’t buy technology.
They buy better EBITDA.

This is the non-negotiable truth of Private Equity.

Most CIOs still believe PE wants:
• New platforms
• AI implementation
• Modern tech stacks
• Big transformation programmes

This is “technology theatre”.

After delivering £1.5M in savings across multiple PE-backed businesses in 10+ countries, one pattern is consistent: 𝐏𝐄 𝐨𝐧𝐥𝐲 𝐛𝐮𝐲𝐬 𝐨𝐮𝐭𝐜𝐨𝐦𝐞𝐬.

Here's the brutal truth. PE partners aren't interested in shiny tech. They need commercial clarity.

They priorities:

𝟏. 𝐌𝐚𝐫𝐠𝐢𝐧 𝐞𝐱𝐩𝐚𝐧𝐬𝐢𝐨𝐧:
Reducing operational cost through vendor optimisation, licence rationalisation, and system consolidation.

𝟐: 𝐑𝐢𝐬𝐤 𝐫𝐞𝐝𝐮𝐜𝐭𝐢𝐨𝐧:
Eliminating technical and vendor debt (including the £500k penalties and £3M true-ups we routinely uncover) that can erode exit value.

𝟑. 𝐀 𝐒𝐭𝐫𝐨𝐧𝐠𝐞𝐫 𝐄𝐱𝐢𝐭 𝐒𝐭𝐨𝐫𝐲:
Building a simple, scalable platform that guarantees growth. Allows the next buyer to pay a higher multiple (as seen in the 10x outcome achieved for one of our clients).

This requires the CIO to become the Chief Value Officer.

Every transformational decision (from renewing a Salesforce contract to integrating a new acquisition) must be tied around its direct commercial outcome— otherwise it's noise.

P.S. What is the single biggest "tech for optics" investment you’ve seen that failed to deliver a measurable EBITDA-level return? Comment ↓

AI in growth planning has moved from experiment to operating system. Five evidence-backed patterns, and what actually changes in your next planning cycle

The shift isn't about faster spreadsheets. It's about fundamentally rethinking how organisations sense, decide, and adapt. Something quiet but profoun

Open article: 5 Ways AI Is Reshaping Growth Planning in 2026 by Daniel J. Jacobs • 5 min read

5 Ways AI Is Reshaping Growth Planning in 2026

Your M&A integration strategy should do one thing above all: protect EBITDA.

Most integrations fail because leaders start with systems rather than commercial reality.

They obsess over:
- Buying new tools
- Implementing platforms
- Rebuilding CRMs
- Chasing “transformation theatre.”
- Forcing teams to adapt before they’re ready

And the consequences are predictable.
Here’s how EBITDA leaks when leaders ignore commercial reality:

𝟏. 𝐒𝐥𝐨𝐰𝐞𝐫 𝐨𝐩𝐞𝐫𝐚𝐭𝐢𝐨𝐧𝐬:
Misaligned teams delay integration by 30–60 days, resulting in £500k+ in EBITDA leakage.

𝟐. 𝐄𝐱𝐭𝐞𝐧𝐝𝐞𝐝 𝐢𝐧𝐭𝐞𝐠𝐫𝐚𝐭𝐢𝐨𝐧 𝐭𝐢𝐦𝐞𝐥𝐢𝐧𝐞𝐬:
Each delay increases deal costs by 10–15%, often adding £500k–£1M in extra operating spend.

𝟑. 𝐒𝐡𝐫𝐢𝐧𝐤𝐢𝐧𝐠 𝐞𝐱𝐢𝐭 𝐦𝐚𝐫𝐠𝐢𝐧𝐬:
A 60–90-day delay can reduce valuation by 0.5x–1.2x EBITA multiples, wiping £5M–£12M from the exit story of a mid-market portfolio company.

And once EBITDA leaks, you almost never get it back.

𝐓𝐡𝐞 𝐭𝐫𝐮𝐭𝐡 𝐢𝐬:
Protecting EBITDA is unrelated to technology.

It begins with stabilising people, contracts, and processes in the first 90 days (long before systems are touched).

Because if teams aren’t aligned, contracts aren’t secured, and processes aren’t controlled, the exit clock is already ticking. Every month of delay permanently erodes value.

This is why the best CIOs ruthlessly remove duplication, noise, and complexity.
They lead with clarity, disciplined sequencing, and clean commercial execution.

The result?

𝐂𝐮𝐭𝐭𝐢𝐧𝐠 £𝟐𝟓𝟎𝐤–£𝟓𝟎𝟎𝐤 𝐢𝐧 𝐞𝐱𝐜𝐞𝐬𝐬 𝐜𝐨𝐬𝐭 𝐰𝐢𝐭𝐡𝐢𝐧 𝐭𝐡𝐞 𝐟𝐢𝐫𝐬𝐭 𝟗𝟎 𝐝𝐚𝐲𝐬 (as we’ve seen repeatedly across multiple PE-backed businesses).

Commercial stability comes first.
Systems come last.

Repost ♻️ if you’re tired of watching the same integration failures repeated across the industry.

P.S. What’s the most expensive integration mistake you’ve seen CIOs make? Comment below ↓

Alt text for the Image: M&A Integration Strategy Fix

Most execs don’t realise it… 
Every time employees use public AI tools for sensitive work, they could be training their competitors’ systems.

After Samsung’s $100M wake-up call, and seeing similar risks across industries. I built a framework to help leaders turn AI governance into a competitive edge.

Read more here: https://lnkd.in/eDRYMFFt

Sally Henderson, your High-Stakes Leadership Mentor

Leadership & Mentoring Expert

The difference between success and failure is not why you lead. It is HOW you lead.

I work with C-suite leaders and executive teams who are already successful and committed to getting better. You come to me when you're navigating high stakes situations, making critical decisions at pace and need to land significant results regardless of the scale of change around you.

Known for my straight talking, direct approach and ability to cut through to what's important quickly, I'm not a classic executive coach. I'm more directive in style and I will share my opinion and advice when the pressure is real and the stakes are highest.

As one CEO client put it: "Working with Sally is a breath of fresh air, a cold shower and warm hug all at once - and brilliant for it."

My work is for C-suite leaders and teams who are serious about mastering their leadership, willing to face the inevitable pain points of real growth, and determined to have a bloody good time doing it.

I'm the creator of The REAL Method, a leadership framework that helps C-suite leaders master their Role, Emotions, Acceleration and Leadership when it matters most. I'm also the author of The HOW of High Performance: Master high stakes leadership, achieve results that matter, and a TEDx and keynote speaker on leadership.

Clients include Accenture Song, Coca-Cola, Forbes, The IPA, IPG, M&C Saatchi, MSQ, NatWest, Nestlé, Next15, Octopus Investments, Reach, Saatchi & Saatchi, Sweaty Betty, The Social Element and VEVO.

"Sally is so much more than a coach or a mentor, she is a personal and professional accelerator! We have worked together on two major transitions – the post-sale integration of our business into fully owned status and my personal transition to corporate EMEA c-suite."
Jackie Stevenson, Global Chief Strategy & Innovation Officer, M&C Saatchi

I take on a limited number of senior leaders and executive teams each year. If this resonates, let's talk: https://www.sallyhenderson.co.uk/

The High-Stakes Leadership Mentor

Trusted expertise in driving leadership and business success for prominent brands and senior leaders.

My passion lies in creating the techniques, models and ideas to help senior teams and leaders to perform at their highest level; especially when the stakes are high. 

A ‘third lane’ for leadership development.

The Real Method™ fills a crucial gap in leadership development - a ‘third lane’ - that goes beyond classic coaching or traditional mentoring. 

To excel as a high-performance team or leader is non-negotiable. 

Executive teams and senior leaders come to me to get the practical and emotional toolkit needed to re-frame their mindset, to give them a clear perspective and the ability to perform even more effectively.

The results are proven and powerful. 

If your executive team and key senior leaders are ready to further accelerate high-performance leadership, we should work together.

Sally Henderson

I want to get my life’s work into as many hands as possible.

So I’m doing something I’ve never done before - a global book tour.

Yes I’m absolutely manifesting the life out of this to make it REAL Emma Harris!

🇬🇧 London
🇦🇪 Dubai
🇺🇸 New York
🇦🇺 Sydney

‘The HOW of High Performance: Master high-stakes leadership, achieve results that matter’ is written for senior leaders navigating change and complexity and gives a structured support system through The REAL Method.

The most successful leaders know they get better with the right help, support and challenge, and I know this book works.

Book tours don’t just happen. They need new connections, the bravery to ask for help, people willing to be generous with their ideas and support, to lean in just because they want to help and know they can.

And I’ve been blown away by just how wonderful and kind people are being. It’s making all the challenge and sheer grit of determination to write this book and put myself out there in the world feel so so worth it.

Good karma showed up recently in the loveliest way. 

I was introduced to a new team in a global organisation I’ve worked with before, and one person told me that a free webinar I’d run over two years ago about landing your dream role had been shared with her by a friend. She said it genuinely helped her get the position she’s in now.

It made me smile so much. You never know where the ripple goes when you put something useful out into the world just because you want to help and know you can, and there she was, living proof it comes back around.

So I’m asking for more of that good karma from you, my LinkedIn network, to help share my life’s work in this book. 

I’m looking for introductions to people who can help me set up Dubai, New York and Sydney, get booked for leadership keynotes, and connect me with brilliant people who can make this tour a success.

If you know someone who’d be brilliant for this, I’d love you to connect us. 

Thank you.​​​​​​​​​​​​😊

Sally Henderson, High-Stakes Leadership Mentor

For C-suite leaders & executive teams in high stakes moments who need straight answers, not endless self-discovery | Creator of The REAL Method | Author | TEDx & Keynote Speaker

No I didn’t win a big pitch.
I lost a pitch
I failed.
I’m no good.

That’s it everything else is going to start to unravel.

Feel familiar!!?

When we ‘fail’ to get an outcome we’ve worked hard for it sucks. It hurts. And it sure does bruise the ego!

BUT.

Winning happens in so many ways.

I did lose a big pitch at the end of last year. A pitch I’d put my heart and soul into, gave up my day off to work solidly on a bespoke brief, tweaked, reviewed, revised and delivered my best in a very tight turnaround. 

And after ALL that effort.
Didn’t win!
But I DID win in so many other ways.

You see at the same time I was under huge pressure to finish my book. The deadline was fixed. I also had many live clients and plenty of BAU demanding my attention and the book had to fit in around these commitments.

Had I won the new gig honestly I think I’d have tipped over into burnout.
I told the global CEO of this client this truth yesterday. That I was actually glad not to have won. They looked a bit shocked at my honesty but I am always about being real.

There will be future opportunities to pitch with the same client, plus many more that will come my way this year. 

The old me would have seriously bled at the perceived ‘rejection’.

The new me could see the naked truth that not winning the pitch wasn’t a failure at all. It was simply the right thing at the right time. 

What have you learnt about handling rejection and how has it helped you?

---

👋 I'm Sally Henderson, High-Stakes Leadership Mentor and specialise in working with C-suite Leaders and Executive Teams; especially through times of complexity and demanding change.

🔔 Follow me for practical tips and advice taken from my REAL Method Programme and decades of experience mentoring the best to help them be even better.

I am SO BORED of all the posts on here merging into one! 

AI is a useful tool and I use it to help me. The more I work with it the less I’ve come to realise it really isn’t a silver bullet. 

You have to have the idea, the content and clarity about your own tone of voice and what you want to stand for. The foundation work and hard work of original thinking can’t be outsourced. Because AI is only a tool and not a sentient unique being. It’s a machine that also often gets it wrong more than right and at times literally lies to you! 

Seeing a comment yesterday from Marco Bertozzi responding to a post offering prompts to get AI to write your LI content, prompted me to add my chat example below to his thoughts agreeing that everyone will just end up looking and sounding the same. The bots talking to the bots! 

Can’t just be Marco and I who are fed up? 

How we express ourselves through language is part of our identity. It reveals our personality, our sense of humour and our beliefs.

Less so when everyone is following Chat so obviously! 

Like this…

Open with a hook.

Say something else that says - it’s not this or this it’s this.

Write. In. Very. Short. Sentences. For. Impact

Maybe
Stack
Them
For 
Visual 
Impact 

Now at 3rd para insert ‘but here’s the thing’ or ‘lets be honest’

Scatter the word ‘actually’ throughout.

Remember it really matters.

And end with a what do you do when bored by generic Chat GPT writing rhythms?

Am I right?!?!! 🤣😭🤦‍♀️😩

Chat has its place but for me originality is way more interesting to read and connect with. 

(No AI was used in this post!!)

Executive teams are not a static entity. They are going through constant change, challenge and curve balls!

Whether your executive team is forming, norming or storming there will be positive and negative dynamics at play. This is totally normal whenever you bring a collection of ambitious, talented and determined individuals together.

The dynamic of positive and negative is to be welcomed and nurtured because no exec team or business every conquered their market or achieved their potential by being 100% aligned all of the time. This is not the role the collective is there to provide.

There is though a gulf of difference between an exec team that can enjoy healthy debate, tolerate friction and keep moving forward well and the exec team where you just scratch the surface and the politics run wildly with people falling down toxic cul-de-sacs of disagreement and mistrust.

An exec team has to have trust in place to be able to embrace their full potential and navigate the rapids of change.

But trust cannot be bought, borrowed or faked. In 2026 trust in and between your top people is a high-performance team leadership trait you simply cannot afford not to have in plentiful supply.

There's a technique from my leadership development programme, The REAL Method that Exec teams love for keeping trust healthy, accelerating growth and nipping any team dynamic problems in the bud.

It's called 'Uncomfortable Truths. Breaking Bread'.

A simple yet effective workshop that guides teams through what really matters when it comes to high performance, healthy team dynamics and successful outcomes.

If you'd like to find out more about Uncomfortable Truths and give your exec team dedicated expertise to help them master HOW they lead - especially through high stakes, drop me a note. 

(I love this picture taken last year when working with the awesome Commercial Senior Leadership Team at Reach. A superb bunch of great humans and collective team high performance)

---

👋 I'm Sally Henderson, High-Stakes Leadership Mentor and specialise in working with C-suite Leaders and Executive Teams; especially through times of complexity and demanding change.

🔔 Follow me for practical tips and advice taken from my REAL Method Programme and decades of experience mentoring the best to help them be even better.

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