Technical Leadership · Applied AI · Enterprise Strategy

Dean
McDonnell

I lead organisations through AI adoption and enterprise transformation — and I still go deep on the architecture.

Leadership roles at Stripe · Intercom · PayPal · ESW

Dean McDonnell, technical leader and Applied AI Architect
$160B+ Annual processing volume advised as trusted technical leader at Stripe
AU$13.6M Revenue uplift led through PayPal APAC technical strategy
15+ Years spanning engineering, pre-sales, TAM, and SE leadership
EMEA & APAC Built and led distributed technical teams across two regions
Portrait of Dean McDonnell

About

A technical leader who can still go deep.

I am an Applied AI Architect and enterprise technology leader with 15+ years helping global organisations adopt frontier AI, modernise platforms, and deliver large-scale digital transformation. My career has been defined by leading high-performing technical teams across EMEA and APAC — partnering with Sales, Product, and Engineering to translate complex challenges into measurable business outcomes.

I have built Solution Engineering functions from the ground up, served as a trusted advisor in Technical Account Management (TAM) to C-suite and VP-level stakeholders, and led architecture engagements spanning AI, cloud, APIs, payments, and SaaS. I develop AI adoption strategies, executive business cases, and operating frameworks that improve productivity, accelerate customer adoption, and establish repeatable best practices — and I ship AI products hands-on, from LLM-powered generation and RAG to transcription, translation, and conversational assistants.

Alongside corporate leadership at ESW, Stripe, Intercom, and PayPal, I founded Faces2Names.com — an AI-native SaaS platform on LLMs and AWS. I am passionate about enabling organisations to adopt frontier AI responsibly, combining technical depth, commercial insight, and people leadership.

Currently seeking: leadership roles (manager through Head of / Director / Principal) in Applied AI, Solution Engineering, Enterprise Architecture, or Customer Technical Leadership — and equally open to senior or principal individual-contributor roles in Applied AI where I can own architecture, strategy, and delivery.

How I lead

What I bring to leadership and principal AI roles.

Not only organisational leadership — deep Applied AI capability. I build the people, processes, and executive relationships that scale delivery, and I design and ship LLM-powered products myself.

Build & scale teams

I have hired, mentored, and developed Solution Engineers and Technical Account Managers; defined career frameworks and operating models; and led distributed teams across EMEA and APAC — including offshore delivery from Sydney into Chennai and Japan.

Shape AI & technical strategy

At ESW, I defined organisational AI strategy with executive business cases and adoption roadmaps. At Stripe, I advised CTOs and VP Engineering on platform strategy, platformisation of payment and billing capabilities, global expansion, and architecture spanning Payments, Billing, Connect, and more.

Win & grow enterprise

I partner with Sales on complex, high-value deals — discovery, architecture, proofs of concept (PoCs) and proofs of value (POVs), security reviews, and RFPs for C-suite buying committees — then own post-sales technical success, adoption, and expansion.

Operational excellence

I standardise discovery, onboarding, approvals, and playbooks; introduce operating metrics and continuous improvement; and apply automation and Applied AI to improve efficiency without losing the human judgement that complex deals require.

Experience

Leadership experience in detail.

From founding an AI product to leading enterprise Solution Engineering and advising strategic Stripe customers — a track record of ownership at scale.

  1. Leixlip, Ireland

    Co-Founder & Chief Product & AI Architect

    Faces2Names.com

    Founded and built an AI-native SaaS platform that enables families to preserve, organise, and discover collective knowledge through intelligent knowledge management, digital storytelling, and collaborative experiences — owning product vision, architecture, and delivery as a solo founder while exploring my next leadership opportunity.

    • Architected an end-to-end AI platform using LLMs for AI-generated autobiographies and eulogies, AI narrated slideshow generation, conversational AI chatbot assistance, speech-to-text and document transcription, multilingual AI translation, semantic search, document understanding, and intelligent content generation.
    • Designed secure, enterprise-grade AI and cloud architecture on AWS (S3, CloudFront, Route 53) with permission-aware AI, scalable REST APIs, and robust security controls including RBAC, MFA, encrypted auth, and signed URLs.
    • Led full product development delivering web and native mobile applications (PHP, JavaScript, MySQL, HTML, CSS, Kotlin, Swift) while defining the product roadmap, user experience, and long-term AI strategy.
    • Engineered advanced media and collaboration capabilities — intelligent media processing, secure document storage, digital legacy planning, knowledge graphs, timelines, messaging, and permission-based content sharing.
    • Defined long-term product vision balancing AI innovation with privacy, security, responsible AI principles, and commercial viability. Web platform live; Android app launched on Google Play.

    Focus LLMs · RAG · Prompt engineering · AI generation · Transcription · Translation · Chatbots · AWS · Full-stack

  2. Dublin, Ireland

    Head of Solution Engineering — Enterprise

    ESW

    Built and led the Enterprise Solution Engineering function for a global cross-border commerce platform — defining the operating model, mentoring a high-performing team, and establishing scalable frameworks for technical discovery, solution architecture, proofs of concept (PoCs), proofs of value (POVs), and customer delivery.

    • Defined the organisation’s AI strategy: evaluating emerging AI technologies and developing executive business cases, adoption roadmaps, and implementation plans covering AI-powered meeting intelligence, workflow automation, sales enablement, operational analytics, and productivity improvements.
    • Drove organisation-wide transformation — redesigning customer onboarding, technical approvals, analytics workshops, implementation governance, and cross-functional collaboration to reduce operational complexity and improve delivery consistency.
    • Developed Solution Engineering playbooks, career frameworks, and technical standards, standardising customer engagement, accelerating onboarding, and creating repeatable best practices.
    • Partnered with executive leadership and enterprise customers to identify AI opportunities, influence product strategy, and deliver business-focused AI transformation initiatives.
    • Led executive customer engagements including discovery workshops, architecture reviews, and PoC / POV sessions — translating complex technical challenges into commercially viable enterprise solutions.
    • Introduced data-driven operating metrics and continuous improvement practices, improving executive reporting, resource planning, and organisational visibility while fostering mentoring, knowledge sharing, and AI-assisted ways of working.

    Initiatives Enterprise AI adoption · SE operating model · Career frameworks · Onboarding optimisation · Executive business cases

  3. Dublin, Ireland

    Senior Enterprise Technical Advisor (TAM)

    Stripe

    Trusted advisor for a portfolio of strategic enterprise customers representing $160B+ in annual payment processing volume — partnering with executive stakeholders to define long-term technology and platform strategies over nearly four years in a senior Technical Account Management capacity.

    • Led enterprise architecture engagements covering global payments, API integrations, distributed systems, and platform scalability — applying platform thinking to how customers adopted and extended Stripe Payments, Billing, Connect, Identity, Financial Connections, and Webhooks.
    • Guided enterprise digital transformation initiatives, advising CTOs, VP Engineering, and Solution Architects on global expansion, automation, AI opportunities, multi-currency processing, recurring billing, and marketplace architectures — bringing Applied AI into strategic platform conversations.
    • Partnered with Product and Engineering leadership to resolve complex architectural challenges, influence product roadmap priorities, and advocate for enterprise customer requirements.
    • Led executive technical engagements — discovery workshops, architecture reviews, implementation planning, and business reviews — driving platform adoption and identifying expansion into new products, markets, and use cases.
    • Improved operational excellence by leading critical technical escalations, developing internal tooling and dashboards, mentoring Technical Account Managers, and establishing trusted executive relationships that enabled strategic technology decisions.

    Domains API strategy · Distributed systems · Payment architecture · Cloud integrations · Security · Executive advisory

  4. Dublin, Ireland

    Senior Presales Engineer — EMEA

    Intercom

    Led technical discovery and architecture design for enterprise SaaS deployments across EMEA, representing the technical voice in complex sales cycles and shaping how enterprise customers adopted Intercom’s platform.

    • Delivered tailored demos, proofs of concept (PoCs), proofs of value (POVs), security reviews, and managed RFP responses for technical buying committees including C-suite stakeholders.
    • Architected API integrations within complex enterprise stacks including CRM and data platforms, and automated onboarding workflows.
    • Partnered with Product to represent enterprise scalability and integration requirements, influencing roadmap priorities based on customer feedback and market trends.
    • Contributed to hiring and team growth, including interviewing candidates and supporting the expansion of the EMEA pre-sales function.
  5. Sydney, Australia

    Lead Sales Engineer — Midmarket, APAC

    PayPal

    Owned technical strategy for 6,000+ mid-market and enterprise clients across APAC, leading delivery with an offshore technical team based in Chennai while based in Sydney — and earning the PayPal APAC regional award.

    • Ensured consistent technical delivery across a distributed APAC customer base spanning multiple markets and time zones.
    • Led API integration and checkout optimisation initiatives spanning fraud, authorisation, and payment flows — driving AU$13.6M annual revenue uplift through reduced drop-off.
    • Delivered executive-level technical reviews and strategic updates to align performance initiatives with commercial objectives.
  6. Sydney, Australia

    Lead Integration Engineer — APAC

    Partnerize

    • Partnered with Sales across the full client lifecycle — from demo to integration and go-live — providing technical consultation and project coordination for API-based SaaS onboarding.
    • Led a Tokyo-based team from Sydney, managing regional delivery and customer onboarding in Japan; played a key role in launching the Japan office, including onboarding the first in-market customers and establishing delivery processes.
    • Analysed performance data to identify growth opportunities; developed internal tools in PHP and JavaScript to improve workflow efficiency and reporting accuracy.
  7. Sydney, Australia

    Lead Engineer — APAC

    PracticeEvolve

    • Managed a client base of 150+ law firms, overseeing end-to-end deployment, solution design, and integrations for a cloud-based legal case management platform.
    • Delivered technical demos, discovery sessions, and infrastructure management across AWS and on-premises environments.
    • Handled technical escalations and maintained executive-level client relationships throughout the customer lifecycle.
  8. Foundation

    IT Help Desk Analyst — Department of Water & Environmental Regulation, Perth (2010–2011): supported 3,000+ employees across WA with Level 1 & 2 support. Founder & CEO — Websites Designed, Galway (2009–2010): secured 18 clients in the first year designing and building bespoke websites.

Founder proof point

Faces2Names.com — leading product, AI, and delivery from zero.

Beyond corporate leadership, I have proven I can own a full product P&L narrative: vision, AI architecture, security, UX, and shipping to production. Faces2Names.com is an AI-powered family storytelling platform that turns conversations and memories into lasting digital legacies — using LLMs for AI-generated autobiographies and eulogies, AI narrated slideshow generation from photos and videos, AI document and audio transcription, multilingual AI translation, semantic search, and an in-app AI chatbot assistant with grounded help and support escalation.

Following redundancy in late 2024, I dedicated focused time to turning a multi-year vision into a live web platform and Android app — while actively exploring my next role. It demonstrates hands-on Applied AI product ownership as well as the strategic judgement I bring to enterprise contexts.

Visit Faces2Names.com
  • AI autobiography & eulogy generation
  • AI narrated slideshow generation
  • AI document & audio transcription
  • Multilingual AI translation
  • In-app AI chatbot assistant
  • Semantic search & document understanding
  • Interactive family tree & merge workflows
  • Life timeline, media, maps & tagging
  • Permission-aware sharing (Owner → Public)
  • Family groups, messaging & document vault
  • Scheduled legacy letters & videos
  • Memorial / RIP discovery
  • Digital legacy & end-of-life planning
  • Web platform live
  • Android app on Google Play

Expertise

Leadership, Applied AI & technical depth.

A full capability map across people leadership, Applied AI product delivery, enterprise architecture, and the industries I know best — built for leadership roles from manager through Head of / Director / Principal, and for senior or principal Applied AI IC mandates.

Leadership & organisation

I build and scale technical organisations — not only as an individual contributor, but as someone who designs operating models, grows people, and partners with executives on outcomes that matter commercially.

  • Solution Engineering leadership — hiring, mentoring, career frameworks, and team operating models
  • Executive advisory and C-suite / VP Engineering stakeholder management
  • Cross-functional leadership across Sales, Product, Engineering, and Customer Success
  • Technical pre-sales leadership — discovery, PoCs, POVs, security reviews, RFPs, and deal strategy
  • Post-sales technical success, adoption, expansion, and escalation ownership as a trusted advisor
  • Distributed team leadership across EMEA and APAC, including offshore delivery
  • Change management, playbook design, and continuous improvement with operating metrics
  • Workshop facilitation — architecture reviews, executive briefings, and PoC / POV sessions

Applied AI

Hands-on Applied AI from strategy to shipped product: LLM architectures, responsible adoption, and production features that customers actually use — demonstrated end to end on Faces2Names.com and through enterprise AI programmes.

  • AI strategy, adoption roadmaps, and executive business cases for organisational transformation
  • Large Language Models (LLMs) — OpenAI, Claude, Amazon Bedrock
  • Prompt engineering, Retrieval-Augmented Generation (RAG), and grounded conversational AI
  • AI content generation — autobiographies, eulogies, and intelligent knowledge synthesis
  • AI narrated slideshow and media generation from photos and video
  • AI document understanding, speech-to-text transcription, and multilingual translation
  • In-app AI chatbot assistants with grounded help and support escalation
  • Semantic search, knowledge management, and AI-assisted workflows
  • AI governance, privacy-aware / permission-aware AI, and responsible AI principles
  • AI meeting intelligence, sales enablement, automation, and operational analytics programmes

Enterprise architecture

Deep experience designing and reviewing complex, high-scale platforms — payments, APIs, cloud, and security — as a trusted advisor to strategic enterprises and as the architect of my own SaaS stack, with a strong bias toward platform thinking and reusable architectural patterns.

  • Enterprise solution architecture and technical discovery for complex SaaS deployments
  • Platform thinking and platformisation — scalable, reusable capabilities across products and regions
  • API strategy, REST API design, webhook architectures, and integration patterns
  • Distributed systems, platform scalability, and resilient payment / billing architectures
  • Cloud architecture on AWS — S3, CloudFront, Route 53, secure media delivery
  • Security & compliance — RBAC, MFA / 2FA, encrypted auth, signed URLs, CSRF protections
  • Stripe platform depth — Payments, Billing, Connect, Identity, Financial Connections, Webhooks
  • Multi-currency, local acquiring, marketplace, and global expansion architectures
  • CRM / data-platform integrations and automated onboarding workflows
  • Internal tooling, dashboards, and operational visibility for technical teams

Industry, product & delivery

Commercial and delivery fluency across fintech, SaaS, and e-commerce — plus full-stack ownership when the mandate requires shipping, not only advising.

  • Industries: SaaS, fintech, payments, e-commerce, cross-border commerce, enterprise software
  • Customer transformation programmes that connect technical architecture to revenue and retention
  • Full product lifecycle ownership — roadmap, UX/UI, APIs, security, and deployment
  • Full-stack delivery: PHP, JavaScript, HTML, CSS, SQL / MySQL, REST APIs
  • Native mobile delivery: Kotlin (Android) and Swift (iOS)
  • Cloud & tooling: AWS, Git, Salesforce, Zendesk, Slack, Microsoft Suite, Google Suite
  • Proof-of-concepts (PoCs), proofs of value (POVs), demos, UAT, go-live coordination, and technical documentation
  • Data-informed delivery — performance analysis, checkout optimisation, and growth insights

Endorsements

How others experience my leadership.

“Dean’s ability to jump on projects or issues of varying complexity, knowing who and when was the right time to tap others where needed, and sift out the noise while focusing on core issues needing prioritisation and path to completion was a breath of fresh air. In our line of work the concepts were always complex, never the same… Dean always found a way to get the job done. Would jump at the opportunity to work with him again in an instant!”

Shaun Harmen Global counterpart

“He stands out as one of the most supportive and forward-thinking leaders I’ve had the chance to work with. He is incredibly organised, always approaching challenges with clarity and structure… What I appreciated most was his genuine openness to new ideas and his willingness to listen and adapt. His ability to balance strategic thinking with hands-on support truly set the tone for a positive and productive team culture. I highly recommend him as a Solution Engineer leader!”

Ugo Torres Former direct report

Credentials

Education & certifications.

Let’s talk

Open to the right opportunity.

I am exploring leadership roles — including manager-level through Head of, Director, and Principal — in Applied AI, Solution Engineering, Enterprise Architecture, and Customer Technical Leadership, as well as senior or principal Applied AI individual-contributor roles where I can own architecture, strategy, and hands-on delivery. Based in Ireland; open to hybrid and remote-friendly structures.

deanomcd@gmail.com

Prefer a guided conversation? Use Ask Dean (bottom-right) — Dean reads every message.

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Faces2Names.com Leixlip, County Kildare, Ireland