Jon Webb Technology & Product Leadership

Chief Technology Officer

Technology leadership built for value creation.

CTO, CPTO and Group CTO across fintech, proptech, edtech and biotech. I create value through technology and product: turnarounds, scale-ups, acquisitions and exits, most recently through a private equity buyout of a £10m+ proptech group.

95%
Of delivered software via governed agentic workflows
£1.5m to £2m
At-risk client ARR recovered
25% to 85%
Increase in technical win rate, helping win NHS, Bupa and Next Retail
1 citation
By the Gates Foundation in 2012, for Mangahigh’s game-based learning
£22m
Exit of Flyt to Just Eat as part of the executive team

Services

Three ways I help.

Tech

Technology & product leadership

CTO, CPTO and Group CTO roles in PE-backed, VC-backed, AIM-listed and privately owned businesses. Board reporting, budgets, regulatory work spanning FCA and ISO 27001, and teams of 5 to 60 across the UK, EU and nearshore.

AI

AI engineering

Agentic development under a governed lifecycle: 95% of delivered software, human review before merge, nothing released without automated verification and test coverage. LLM automation embedded into core operational workflows, reaching 50% auto-approval on key decision processes while cutting the operational headcount needed to run them by 40%.

M&A

M&A & due diligence

Seven buy-side and sell-side transactions: technical due diligence, post-merger integration, seller-side diligence, exit and buyout. Cost restructuring and value creation mandates.

Positioning

Where I sit.

Most technology leaders operate in one lane. I sit in the overlap, where technical decisions, product direction and commercial outcomes have to agree.

Venn diagram of technology, product and commercial Three overlapping circles labelled technology, product and commercial, with a marker at the centre where all three meet. Technology Product Commercial JON WEBB

Key achievements

A record of outcomes.

2026
Led technology through a private equity buyout of a £10m+ proptech group following buy-and-build integration.
2022
Solidified Wagestream’s position as the #1 provider of on-demand pay to the public health sector.
2019
Part of the executive team that exited hospitality technology business Flyt to Just Eat for £22m.
2016
Turnaround and exit of digital agency Chroma Sports to a top-5 gambling business.
2012
Launched edtech Mangahigh into 4 countries. The Gates Foundation annual letter cited it as a successful game-based learning company.

Experience

Selected engagements.

Earlier roles

  • DNA Worldwide, Interim Group CTO: re-architected a D2C ancestry product across genome processing, data pipelines and lab management.
  • Growth Street, Interim VP Engineering: turnaround plan approved by the board; delivery frequency from monthly to three times weekly.
  • Fitbug (AIM listed), Interim CTO: halved operating costs, pivoted B2C to B2B, releases from monthly to five times a week.
  • Chroma Sports, Chief Product & Technology Officer: turnaround executed and business sold to Editec Lotteries for £3m.
  • TransferGo, CTO: recovered a failed launch in a month; customers grew from 12,000 to 100,000; transaction processing time down 70%.
  • Mangahigh, CTO: scaled a global edtech to 2 billion maths games a year; teams from 3 to 35; cited in the 2012 Gates Foundation annual letter as a successful game-based learning company.
  • 1998 to 2010: engineer to architect to head of systems across two top-5 European digital agencies, an insurtech and IoT adtech businesses.

Testimonials

In their words.

Leadership

“
During his tenure Jon has played a key role in stabilising, modernising and consolidating the Group’s technology function through multiple merger and acquisition activities and significant organisational change.
Canopy & The Lettings Hub Official reference
“
Jon took the bull by the horns and added structure, people, breadth and depth to almost all areas of the business, whilst tackling the many fires tech startups experience, before they could turn into infernos.
Tom Weaver CEO, Flyt
“
We hired Jon to restructure the engineering team, with the goal of improving productivity and happiness levels. Jon far surpassed my expectations and those of the team. I look forward to seeing which company Jon transforms next!
Greg Carter CEO, Growth Street

Colleagues

“
Jon didn’t just show us a better way of working, he did the invisible work behind the scenes too, and was always a champion for the team.
Team Member Canopy & The Lettings Hub
“
A breath of fresh air, and exactly what the tech team needed. Thank you for all the advice and support.
Colleague Canopy & The Lettings Hub
“
Jon picked us up out of the mess when the merger happened. It was so refreshing to finally have real, strong tech knowledge in the business.
Senior Colleague Canopy & The Lettings Hub

Insights

Writing on what works.

Governance

Everyone in your business is now a developer

Engineering wants control, the business wants tools now. Seven steps that let both happen without a breach, and without Engineering acting as gatekeeper.

Read the article →
AI

AI that decides: Jev and the OpenAI Decisions API for business leaders

Two new products pick an answer from a fixed list instead of writing text. What that means for cost, speed and control, and how to test it.

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M&A

Navigating the nuances of technical due diligence

What buyer-side and seller-side technical due diligence actually means, and the questions that matter on both sides of the table.

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Strategy

Buy vs. build for today’s CFOs

Buy a ready-made SaaS solution, or build bespoke in-house? A practical framework for CFOs weighing the trade-offs.

Read the article →
PE backed VC backed AIM listed Privately owned Fintech Proptech Edtech Biotech Turnaround M&A Post-merger integration Value creation Scale-up

Contact

The next value creation opportunity is a conversation away.

If any of this sounds like your business, I would love to hear from you.