Matt Stephenson
CTO / Transformation Leader
Based in United Kingdom · 33+ years experience
Summary
Technology Leader | The Common Sense CTO | Founder at Stepthinking | Strategy, Transformation, Delivery, Mentoring | Helping Software-Led Businesses Get Unstuck
About
I help businesses whose success depends on technology get clarity, control, and momentum when things have become complex, stuck, or misaligned.
EXPERIENCED TECHNOLOGY SENIOR LEADER
HOW I CAN HELP YOU
I operate as a CTO, Technology Leader, or Adviser, working with Founders, MDs, Boards, and Leadership Teams to provide experienced, hands-on leadership where it matters most.
This can be in a permanent capacity, or through interim and fractional engagements where businesses need immediate impact without long ramp-up times.
If your business is at a change point around growth, platform refresh, organisational reset, post-investment pressure, or where delivery is no longer keeping pace, I can help.
My focus is on technology strategy and transformation that actually lands. That means:
✅ Defining clear, pragmatic technology strategies aligned to business goals
✅ Stabilising and modernising critical platforms
✅ Designing operating models and team structures that work in practice
✅ Improving delivery, accountability, and decision-making
✅ Leading teams directly where confidence, clarity, or momentum has been lost
WHO AM I?
📌 30+ years’ experience across B2B and B2C environments including SaaS, retail, e-commerce, insurance, aviation, automotive, and data-driven businesses
📌 Proven track record operating at board level and leading teams from 10 to 150 people
📌 Delivered complex transformations spanning people, process, and technology in both regulated and fast-moving commercial environments
📌 Known for a pragmatic, outcomes-led approach — focusing on what works rather than over-engineering solutions
📌 Comfortable operating across the full spectrum: strategy, transformation, and hands-on leadership execution
If you need a senior technology leader to help modernise, stabilise, or reset your technology and teams, whether on a permanent or flexible basis, get in touch and let's start a conversation.
Please contact me at matt@stepthinking.com
Skills
Software Architecture, M&A / Due Diligence, Platform Modernisation, Engineering Leadership, Vendor Management
Regions covered
Industry experience
Fintech, Professional Services, Retail, SaaS, Education
At a glance
Matt brings hands-on experience across Software Architecture, M&A / Due Diligence, Platform Modernisation, Engineering Leadership, Vendor Management. Available for engagements across United Kingdom, Ireland. Industry experience includes Fintech, Professional Services, Retail, SaaS, Education.
How fractional CTO engagements with Matt work
Matt works on a fractional basis — typically one to three days a week for an agreed engagement length — so you get senior technical leadership without the cost or commitment of a full-time hire. Engagements commonly include technical due diligence, board reporting, engineering team leadership, technology strategy, architecture reviews, hiring support, and stepping in as interim CTO during a transition.