Fractional CTO & Board Advisory
Technology leadership,
without the overhead
Strategic guidance for startups, scale-ups, and nonprofits navigating complex technology decisions. Former Amazon engineering leader. SaaS founder. Startup advisor.
- 25+
- Years in Technology
- 8+
- Years at Amazon
- 15+
- Years building sheepCRM
Selected experience
About
I'm James Webster, founder of Croftsware and creator of sheepCRM — a membership and relationship CRM platform I built from scratch and have operated for over 15 years, serving membership organisations, charities, and nonprofits across the UK.
My career spans more than two decades of technical leadership, from Amazon — where I progressed to Senior Software Development Manager overseeing core retail catalogue systems and managing engineering teams across multiple countries — to working with a wide range of SaaS businesses and venture-backed startups.
Since leaving Amazon, I've founded and maintained software products, built and handed over engineering teams, and served as a trusted technical lead during periods of growth, transition, or restructuring. My work has included supporting startups such as Rangespan (later acquired by Google), as well as advising organisations on architecture, delivery processes, and operational readiness.
Based in Oxfordshire and working remotely, I partner with organisations that need senior technology leadership but don't require a full-time CTO. Whether you're a non-technical founder making your first engineering hire, or a board seeking independent technical oversight, I bring long-term experience, practical judgement, and a calm, delivery-focused approach.
Services
Four ways I work with organisations. The boundaries are softer than the labels suggest — most engagements start as one and borrow from another.
Fractional CTO
Embedded part-time technology leadership. I join your leadership team to set technical direction, build engineering culture, and make sure your technology investments earn their keep.
Non-Executive Director
Independent board-level technology oversight. I bring technical judgement to governance, so the board can ask the right questions and understand the answers.
Technical Due Diligence
Structured assessment of technology assets, teams, and practices for investors, acquirers, or boards. Clear findings and actionable recommendations, in two to four weeks.
Advisory
Strategic counsel on a specific challenge: architecture, AI adoption, vendor selection, team structure, or roadmapping. Light-touch retainer, no minimum commitment.
Recent writing
New Motor, Old Belts
Cheap software does not redesign a firm. The mills only changed shape because the buildings wore out, and software never wears out. Until the old thing is cheap to throw away, you are bolting a new motor onto old belts.
Nobody Gets Fired
Every founder believes the better product wins. In business-to-business it does not, and the reason is not that buyers are stupid. They are answering a different question from the one you are pitching. On the uncertainty tax, the safe incumbent, and why the challenger wins not by proving superiority but by making the change short enough to survive.
The Memory That Won't Compress
The vendors say agent memory is solved - extract the facts, embed them, retrieve on demand. But the institutional memory that actually stops an agent repeating your worst mistake is felt history, and felt history resists embedding by construction.
Approach
"Good technology decisions are business decisions. My role is to translate between the technical and commercial, ensuring technology serves strategy—not the other way around."
Pragmatic, not dogmatic. I favour proven approaches over fashionable ones. The right solution depends on your context, constraints, and ambitions.
Candid counsel. You're engaging me for honest perspective, not validation. I'll tell you what you need to hear, constructively.
Knowledge transfer. I aim to build your organisation's capability, not create dependency. Success means you need me less over time.
How I work
Every engagement starts with a conversation — no pitch decks, no sales process. We talk about where you are, what's working, and what isn't.
Embedded leadership
For fractional CTO and NED roles, I typically work one or two days per week, joining your leadership meetings, mentoring your engineering leads, and owning technical strategy. Engagements usually run for six months or longer.
Focused assessments
For technical due diligence or specific architecture reviews, I deliver a structured report within two to four weeks — clear findings, honest assessment, actionable recommendations.
Advisory
For ongoing counsel, I work on a light-touch retainer — available when you need a sounding board for hiring decisions, vendor evaluations, or technology strategy. No minimum commitment.
Get in touch
Interested in working together? I'd welcome a conversation about your situation and how I might help.