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.

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25+ Years in Technology
8+ Years at Amazon
15+ Years building sheepCRM
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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.

LinkedIn profile CTO Playbook podcast — Ep. 77
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Services

Fractional CTO

Embedded technology leadership on a part-time basis. I join your leadership team to set technical direction, build engineering culture, and ensure your technology investments deliver value.

Non-Executive Director

Independent board-level technology oversight. I bring technical expertise to governance, helping boards ask the right questions and understand technology risk and opportunity.

Technical Due Diligence

Assessment of technology assets, teams, and practices for investors, acquirers, or boards. Clear-eyed evaluation with actionable recommendations.

Advisory

Strategic counsel on specific challenges: architecture decisions, vendor selection, AI adoption, team structure, or technology roadmapping. Flexible engagement for focused problems.

Recent writing

Fifteen Years of sheepCRM The End of Simplicity The Three Mountains

All writing

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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.

04

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.

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Get in touch

Interested in working together? I'd welcome a conversation about your situation and how I might help.

Schedule a call james@croftsware.com