Andrew Flegg

Technology, product & commercial executive // Board-level advisor

Andrew Flegg

Summary

Senior technology, product and commercial executive operating at C-suite level in a FTSE 250 software company serving complex, regulated finance organisations. Andrew has helped make two of Alfa’s defining strategic technology shifts: the full replatforming of Alfa Systems to a modern Java web platform, and the later transition to Alfa Cloud and SaaS. He builds and runs bank-grade technology organisations, balancing architecture, cyber risk, operational resilience, customer trust and commercial outcomes. Known for plain-spoken board judgement, hands-on client leadership and the ability to turn deep technical choices into durable business advantage across the full executive agenda.

Executive Experience

Chief Technology Officer

(2019 – present)

Alfa Financial Software (Global)

Owned Alfa’s global technology, product and platform strategy across Product, Engineering, SaaS, Internal Technology, Information & Cyber Security, Solution Architecture and the wider Alfa Systems ecosystem — spanning product direction, cloud operations, cyber resilience, customer trust, commercial risk and board-level technology governance:

  • Led Alfa’s technology strategy for a bank-grade SaaS platform used by major regulated finance organisations, balancing long-term architecture, operational resilience, cyber risk, customer trust and commercial outcomes.
  • Represented Alfa externally with customers, prospects, investors, analysts and industry audiences, translating cloud, SaaS, AI, data and architecture choices into clear business judgement and market confidence.
  • Partnered with the CEO, CRO, COO, CFO, executive leadership and board on technology investment, execution risk, commercial trade-offs, forecasts, budgets and strategic priorities.
  • Led scalable, secure platform development; strengthened developer experience, continuous delivery and operational feedback loops; and used field experience to inform product roadmap, platform direction and customer outcomes.
  • Evaluated locations and established nearshore teams in Gdańsk, Poland for both 24/7 Cloud Operations and software engineering, expanding delivery capacity while protecting culture, accountability and service quality.
  • Led technology governance across assurance, audit and regulatory expectations, including ISO 27001/27018, SOC 1/2 Type II and GDPR data processor responsibilities.
  • Led and participated in final-stage customer contract negotiations as required, with — or instead of — the Chief Executive Officer and/or Chief Revenue Officer.
  • Built leadership capability, strengthened cross-functional alignment, and ran the function with clear accountabilities, budgets and a personable, plain-spoken leadership style that helped teams make good decisions and do their best work.
  • Managed a global team of ~270 people across 4 departments; with an annual budget of ~£9M (excluding staff). Scaled Alfa Cloud with &30% CAGR, supporting major regulated finance customers with secure single-tenant environments, 24/7 operations, and strong assurance controls.
Andrew Flegg andrew@flegg.org  |  linkedin.com/in/aflegg  |  +44 7956 366652

Executive Experience (continued)

Head of Solution Architecture

(2016 – 2019)

Alfa Financial Software (Global)

Led the shift from customer-managed, on-premise deployments to Alfa-managed cloud and SaaS, turning Alfa’s product architecture into an operational and commercial advantage. Built solution architecture capability, reduced delivery risk and cost, and helped establish a cloud-first model that gave customers the benefit of Alfa’s own operating expertise, security posture, upgrade discipline and platform knowledge. This laid the foundations for Alfa Cloud’s later scale and for a more repeatable, resilient SaaS business model.

Lead Delivery Architect & Director

(2013 – 2016)

Alfa Financial Software (US)

Executive-level technical lead on major US deployment for a top automotive finance company, owning architecture decisions and how Alfa Systems fit into a wider enterprise landscape. Drafted contracts/SOWs, contributed to US management and sales activity, and handled sensitive technical escalations across projects.

Lead Product Architect & Senior Manager

(2007 – 2013)

Alfa Financial Software (EMEA)

Led Alfa’s defining product transformations: the full replatforming of Alfa Systems from a mature AS/400-era monolith to a modern Java web application, preserving deep asset-finance functionality while creating the architectural basis for future scale, upgrades, APIs and cloud. Built tooling to convert and protect years of proven source-code investment rather than starting again from a blank sheet; helped shift engineering to a product-led, test-driven, iterative delivery model; and engaged directly with board, CEO, COO, customers and prospects on technology positioning, implementation risk and commercial credibility.

Senior Consultant

(2005 – 2007)

Alfa Financial Software (EMEA)

Delivered development, support and consultancy across asset finance projects, including enhancements to the legacy platform, data migrations, and framework development.

IBM

Developer & team leader roles (2000 – 2005)

Ford Motor Company

Early-career software development roles (1997, 1998 – 1999)

Jaffa Software

Founder: developer of RISC OS, open source & mobile software (1995 - 2020)

Board/Advisor Experience

Founding Board Advisor

(2026 – present)

The Women’s Association start-up

Hands-on advice and support during bootstrap phase of a technology start-up providing a platform for women and girls. Transitioning to ongoing advisory/Board role providing input on strategy, platform evolution, user trust, AI, data governance and ethical risk.

Impact Council Member & CEO Advisor

(2025 – present)

DIAL Global

Technical and Board steering for development of AskDIAL AI chatbot to expedite customers finding insights from multi-year reports. Ongoing participation in the Council, which brings together diverse perspectives across sectors to explore what inclusive, responsible leadership really looks like in practice; and how it’s embedded into culture, talent, and decision-making.

Founder, Member, Chair (2008 – 2011)

Maemo Community Council

Founded and chaired the Maemo Community Council to create an interface between Nokia and a large open-source community. Built consensus across stakeholders with different incentives; served multiple elected terms.

Andrew Flegg andrew@flegg.org  |  linkedin.com/in/aflegg  |  +44 7956 366652

Media/Appearances

Alfa's Intelligence - a conversation with the CTO

Podcast (2026)

Panmure Liberum

Harvey Robinson and Andrew look at the evolution of software development. Over the last 70+ years it is very clear that as software has become less complex to write, the problems it solves have got more complicated and the number of software engineers has grown exponentially. They also discuss moats from domain expertise, functionality, agile development, deep customer relationship, to trust, track record and operational expertise.

Alfa's CTO and CEO on Technology

Video (2025)

Alfa Financial Software

In this recorded discussion with Alfa’s CEO, Andrew reflects on how long‑term platform decisions shape what organisations can reliably do with technology. He discusses cloud‑native architecture, single‑version SaaS, continuous delivery, and the practical use of AI in regulated environments—arguing that durable advantage comes from clear trade‑offs and engineering discipline, not hype.

Navigating the AI landscape in the asset finance space

Interview (2024)

Leasing Life

In this industry round‑up on AI in financial services, Andrew offers a grounded perspective on where AI is genuinely delivering value—and where caution is warranted. He addresses practical applications such as decisioning and fraud, alongside concerns around data quality, bias, and regulation, arguing that successful adoption depends less on ambition and more on disciplined execution and context‑aware design.

Talking with... Andrew Flegg

Podcast (2022)

Be-IT: Talking with Tech Leaders

“Most Tech Leaders get started pretty early. Andrew was already getting to grips with rudimentary programming when he was still in short trousers. So it’s perhaps no surprise that he’s risen to become the Chief Technology Officer at Alfa Systems, the multinational asset finance software giant.”

What does the post-Covid leasing industry look like?

Keynote (2022)

Leasing Life

In this adapted keynote from the Leasing Life Conference, Andrew reflects on how the shocks of recent years—from Covid to macro‑economic and regulatory change—have reshaped expectations of technology in asset finance. He argues that differentiation now comes from combining adaptable platforms with resilient culture, enabling organisations to respond to uncertainty with speed, empathy, and durable competitive advantage.

In Conversation with... Andrew Flegg

Podcast (2020)

Finance & Leasing Association

Interviewed by Simon Goldie, the FLA's Head of Asset Finance, Andrew discusses how artifical intelligence and machine learning can transform business and customer experiences in asset finance, plus how to begin incorporating AI into operations.

Patents