Insights

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Opinion and insight from our events and community, on everything from AI and payments to fundraising and regulation.

AI11 insights

Insights · Oct 2026The AI Product Decision: What to Build, What to Buy, and What to Leave AloneMost fintechs aren't trying to build the next frontier AI model. The real decisions sit higher up the stack: what to own, what to rent, and where AI shouldn't be used at all. Here's how three operators are making those calls.By Calypso HarlandFeaturing Oliver Smith, Money20/20 · Chris Corbett, Plaid · Sasha Haco, Unitary AI · David Weinstein, KayOS
Insights · Oct 2026From Copilots to Agents: What’s Actually Ready to Run Your WorkflowsCopilots help. Agents own the work. The difference matters more than the label – and the fintechs getting it right are the ones engineering for oversight, not just automation. Here’s what’s actually running in production.By Calypso HarlandFeaturing Sophia Furber, S&P Global · Sean Hederman, Zilch · Neal Lathia, Gradient Labs
Insights · Oct 2026AI vs. The Old Guard: Rewiring the Plumbing of FinanceAI is collapsing the cost of building financial infrastructure. The advantage is shifting from the banks that built to last to the fintechs that build to evolve.By Calypso HarlandFeaturing Nick Levy, IBM Consulting · Svetlana Hoffman, epta-x · Karen Ruddich, sherloc · Sandi Samantaray, AI Alignment
The AI Security Reckoning: Why Your Next Breach Could Be Your AI
Insights · Aug 2026The AI Security Reckoning: Why Your Next Breach Could Be Your AIFirms are racing to roll out LLMs while security lags behind. The next big fintech breach may not be a data leak – it may be your own AI being turned against you.By Calypso HarlandFeaturing Sally Walker, formerly UK Ministry of Defence · Sarah Sinclair, Co-Labs · Kate Brimsted, Shoosmiths
Agentic AI: Moving from Auto-complete to Auto-pilot
Insights · Jul 2026Agentic AI: Moving from Auto-complete to Auto-pilotChatbots that summarise a document are old news. The scaling opportunity is in AI that takes a goal, plans the steps and gets it done – without you micromanaging every move.By Calypso HarlandFeaturing Simran Singh, FCA · Mike Curtis, Multiply AI · Tom Winstanley, NTT DATA · Aditi Subbarao, Instabase
AI as the Growth Engine: How Fintechs Are Winning with Applied AI
Insights · Jul 2026AI as the Growth Engine: How Fintechs Are Winning with Applied AIThe experimentation phase is over. The fintechs pulling ahead are the ones using AI to change their unit economics, not to decorate a pitch deck. Here’s what that looks like in practice.By Calypso HarlandFeaturing Liz Lumley · Teo Blidarus, FintechOS · Derek Freel, Google Cloud · Katharine Wooler, Softcat
How Advai Built an AI Fintech Without the Hype
Insights · May 2025How Advai Built an AI Fintech Without the HypeA behind the scenes look at how Advai has used AI to scale rapidly. Chris Jefferson, Founder and CTO at Advai shares real insights with Money2020’s Ian Horne on funding, operational challenges, and AI’s impact on growth.By Calypso HarlandFeaturing Chris Jefferson, Advai · Ian Horne, Money20/20
The AI Investment Landscape – Where’s the Real Money Going?
Insights · May 2025The AI Investment Landscape – Where’s the Real Money Going?At Fintech Fringe’s Rise & Shine session on AI Investment & Scale: Where the Smart Money is Going, moderator Ian Horne opened the panel with a straight-talking challenge to the room:By Calypso HarlandFeaturing Ian Horne · Christian Nentwich, 13 Books Capital · Alexandra Edmonds, Mastercard · John Spindler, TwinPath
AI as the Next Fintech Gold Rush
Insights · May 2025AI as the Next Fintech Gold RushIn this keynote, Charles Kerrigan, Partner at CMS and author of AI Law and Regulation , pulled back the curtain on how AI is reshaping fintech investment.By Calypso HarlandFeaturing Charles Kerrigan, CMS
The Future of AI in Financial Services – Risks, Regulation & Real-World Impact
Insights · May 2025The Future of AI in Financial Services – Risks, Regulation & Real-World ImpactFrom startup missteps to regulatory blind spots, AI in financial services is hitting hard questions.By Calypso HarlandFeaturing Katharine Wooler, Softcat · Lisa McClory, CMS · Nick Rogers, Wagestream · Emre Kazim, Holistic AI
Generative AI’s Ripple Effect: Payments Beyond Automation
Insights · Apr 2025Generative AI’s Ripple Effect: Payments Beyond AutomationHosted on the Innovation Stage at Pay360 by Fintech Fringe, this standout session brought together AI leaders from Google, Nvidia, and Alipay to showcase how generative AI is already transforming the payments landscape.By Calypso HarlandFeaturing Joy Macknight · Eva Zhang, Alipay UK · Georgios Kolovos, Nvidia · Ronan Carter, Google
Insights · Feb 2024Rise & Shine: Expert Tips for Fintechs Navigating AI RegulationIn a packed room at last week’s Rise & Shine event, the spotlight was on the future of AI regulation, unravelling strategies for Fintechs to futureproof their approach by learning how to cultivate trust and manage risk in what is relatively unchartered territory. Douglas Mackenzie, an expert moderator from FF News | Fintech Finance, skillfully

Fundraising3 insights

Using Financial Diligence as a Growth Lever
Insights · Apr 2026Using Financial Diligence as a Growth LeverThe final stage of a fundraise is often viewed as a hurdle to be cleared, but good due diligence and financial hygiene is a primary building block for business value and a "green factor" for investors.By Calypso HarlandFeaturing Karen Allan, HaysMac · Lucy Tobutt-Denny, HaysMac
Architecting the Capital Stack: Avoiding the "Crocodile"
Insights · Apr 2026Architecting the Capital Stack: Avoiding the "Crocodile"In 2026, the "Capital Stack" is no longer a straight line to the next equity round.By Calypso HarlandFeaturing Regina Lau · Alex Mayall, Anthemis · Devin Kohli, Outward VC · Nitya Gupta, 13books Capital
What fintech founders need to know about storytelling for fundraising
Insights · Apr 2026What fintech founders need to know about storytelling for fundraisingIn this Scale & Grow workshop, Nicky Harrison and Anna Jones of Nanta Partners provided a pragmatic guide to one of the most underestimated skills in a founder's toolkit.By Calypso HarlandFeaturing Nicky Harrison, Nanta Partners · Anna Jones, Nanta Partners
Insights · Nov 2024Rise & Shine: Fundraising in 2025 – How to Keep the Competitive EdgeThe latest Rise & Shine session, hosted by Fintech Fringe, brought together fintech founders, VCs, and corporate investors at Rise London to discuss the future of fundraising as we approach 2025. Industry experts shared personal insights into the shifting investment landscape, strategies for growth, and the importance of building lasting partnerships. Key themes
Insights · Mar 2024Rise & Shine: Fundraising Tips for Female Founders in FintechIn a tribute to International Women’s Day, yesterday’s Rise & Shine event, sponsored by Rise, created by Barclays addressed the challenges facing women in Fintech looking to fundraise and explored the practical ways we can shift the needle.

Marketing6 insights

Insights · Oct 2026Unit Economics: The Metrics That Actually Matter to Your BoardBoards don’t buy reach and impressions. Here’s how to talk about marketing in the language of revenue, risk and predictability – and finally earn your seat at the table.By Calypso HarlandFeaturing Vivienne Hsu, Anabasis Partners · Regina Lau, Weavr · James Hannaford, Sokin · Tina Fisher, Vyntra
Insights · Aug 2026Founder-Led Content That ConvertsWhen most marketing content is generic and machine-made, the founder’s authentic voice is the one advantage a competitor cannot copy. Here is how to use it to build a pipeline based on authority rather than volume.By Calypso HarlandFeaturing Richard Hudson, DNA Payments · Araminta Robertson, Mint Studios
Insights · Aug 2026Brand or Be Forgotten: Why Brand Is the Final Frontier of Fintech ScalingIn a crowded market, your product gets you noticed and your brand gets you remembered. Here is how the people behind some of fintech’s strongest names think about the emotional unlock that separates the household names from the also-rans.By Calypso HarlandFeaturing Miranda McLean, Ecommpay · Neil Cooper, Starling · Gareth Morgan, Revolut
Insights · Aug 2026The Human ROI: Why Story Is the Engine That Earns AttentionThe best fintech stories make the technology invisible. Here is how marketing leaders turn complex products into a single human truth that customers actually remember.By Calypso HarlandFeaturing Jana Straiton, Renegade Marketing · Laura Watkins, 11:FS · Nicola Harley, Morningstar · Georgie Burks, Allica
Caffeine, Duct Tape and Data: How to Hack Your First 100,000 Users
Insights · Aug 2026Caffeine, Duct Tape and Data: How to Hack Your First 100,000 UsersEarly growth isn’t a smooth line on a chart. It’s scrappy, manual and occasionally a bit magic. Here’s how operators from Revolut and Wallet in Telegram actually found their first users.By Calypso HarlandFeaturing Lucy Heavens, Heavens Sent · Chad West, Ready · Irina Chuchkina, Wallet in Telegram
The Future of Trust in Fintech: Building Loyalty in the AI Era
Insights · Jul 2026The Future of Trust in Fintech: Building Loyalty in the AI EraAs AI makes more of the decisions, transparency is no longer enough. The fintechs that win loyalty are the ones that can prove their systems are working on the customer’s side.By Calypso HarlandFeaturing Kristina Mydlar, Mydlar Consulting · Charlotte Hill, Penningtons Manches Cooper · Tim Joslyn, Paymentology · Fi Sellick, Square
Insights · Oct 2024Rise & Shine: Marketing in 2025 – Strategies to ThriveThe latest Rise & Shine event explored how fintech marketers can prepare for the challenges of 2025. We focused on maintaining authenticity amidst the rise of AI, the power of user-generated content (UGC) and influencers, and how human connections are more critical than ever in a digital world. SPEAKERS Moderator: Ian Horne, Head

Payments8 insights

Why the Plumbing is Now the Headline
Insights · Jul 2026Why the Plumbing is Now the HeadlineAgentic AI, a wave of M&A and stablecoins quietly rewiring the money stack. Here’s what’s in, what’s out, and why the boring infrastructure is the real story.By Calypso HarlandFeaturing Ian Horne · Oliver Smith, Money20/20
How Customer Experience Fuels Growth in Payments
Insights · Apr 2025How Customer Experience Fuels Growth in PaymentsHosted on the Innovation Stage at Pay360 by Fintech Fringe, this fireside chat brought together leaders redefining the payments experience through brand and customer-centric thinking.By Calypso HarlandFeaturing Simon Taylor, Sardine · David Sandström, Klarna · Kamjar Hajabdolahi, Kustom
Mobilising Ecosystems: "How Big Brands Are Driving Payments Innovation"
Insights · Apr 2025Mobilising Ecosystems: "How Big Brands Are Driving Payments Innovation"Hosted on the Innovation Stage at Pay360 by Fintech Fringe, this fireside chat explored how big brands - retailers, telecoms, and mobile operators, are reshaping the payments landscape.By Calypso HarlandFeaturing Lana Hoffmann, epta-x · Stuart Neal, Boku
Retail Reinvented: Payments at the Heart of Customer Experience
Insights · Apr 2025Retail Reinvented: Payments at the Heart of Customer ExperienceHosted on the Innovation Stage at Pay360 by Fintech Fringe, this panel explored how payment technology is driving more personalised, seamless, and loyalty-enhancing customer experiences in retail.By Calypso HarlandFeaturing Gina Carke, The Fintech Times · Samina Hussain Letch, Square · Kamjar Hajabdolahi, Kustom · Divya Bhardwaj, Uber Payments
Rethinking BNPL: Credit Innovations for Tomorrow
Insights · Apr 2025Rethinking BNPL: Credit Innovations for TomorrowHosted on the Innovation Stage at Pay360 by Fintech Fringe, this panel took a fresh look at the Buy Now Pay Later (BNPL) revolution.By Calypso HarlandFeaturing Angela Yore, SkyParlour · Melinda Roylett, Lloyds Bank · Silvia Mensdorff-Pouilly, Worldpay
Embedded Payments: The Secret Growth Engine
Insights · Apr 2025Embedded Payments: The Secret Growth EngineHosted on the Innovation Stage at Pay360 by Fintech Fringe, this panel showcased how embedded finance is powering scalable, seamless customer experiences across sectors.By Calypso HarlandFeaturing Dan Lowther, CCGroup · Iana Dimitrova, OpenPayd · Andy Ellis, NatWest Boxed · Adam Moulson, Griffin
Super Wallets: "The Next Frontier in Digital Payments"
Insights · Apr 2025Super Wallets: "The Next Frontier in Digital Payments"Hosted on the Innovation Stage at Pay360 by Fintech Fringe, this session explored the evolving world of AI-powered digital wallets, also dubbed 'super wallets'.By Calypso HarlandFeaturing Elizabeth Lumley · Martin Masser, TON Foundation · Lynne Lagan, Lloyds Banking Group · Edoardo Volta, Curve
Tokens and Stablecoins Rule: Payments Without Borders
Insights · Apr 2025Tokens and Stablecoins Rule: Payments Without BordersHosted on the Innovation Stage at Pay360 by Fintech Fringe, this panel brought together legal, policy, and innovation leaders to explore the role of tokenisation and stablecoins in reshaping global payments.By Calypso HarlandFeaturing Riccardo Tordera Ricchi, The Payments Association · Natalie Lewis, Travers Smith · Tom Duff Gordon, Coinbase · Andrew MacKenzie, Agant

Regulation3 insights

Insights · Nov 2026Turning Compliance into a Growth StrategyCompliance has long been seen as the brake on growth. The fintechs pulling ahead treat it as a capability – investing in policy and data up front, bringing compliance in from day one, and putting AI to work on the heavy lifting. Here’s what that looks like in practice.By Calypso HarlandFeaturing Amanda Harrison, fscom · Ashley O’Reilly, Corlytics · Jared Taylor-Davies, Bain
Insights · Nov 2026RegTech That Actually Works: Moving Beyond Checkbox ComplianceThe box-ticking era is running out of road. The firms getting real value from RegTech are using it to reduce risk and free up room to innovate, not to produce prettier evidence for the regulator. Here’s what that looks like in practice.By Calypso HarlandFeaturing Amanda Harrison, fscom · Francis Mariniere, Moody’s · Marius Jurgilas, Axiology
Regulation Backed Innovation: Enabling New Technologies to Flourish
Insights · Apr 2025Regulation Backed Innovation: Enabling New Technologies to FlourishHosted on the Innovation Stage at Pay360 by Fintech Fringe, this panel explored how regulatory frameworks like the FCA’s AI Sandbox can empower innovation while safeguarding compliance.By Calypso HarlandFeaturing Claire Conby, Finnovation UK · Dr Louise Beaumont, Mastercard · Heather Lee, SWIFT · Tom Bull, EY
Insights · Sep 2024Rise & Shine: The Vital Role of Regulatory Compliance in ScalingWe kicked off our first “Rise & Shine” event post-summer talking all things regulation. It was a full house bringing together leading experts to discuss why it must be prioritised in any fintech growth strategy. Read on to hear our expert’s top tips. Opening Discussion: Revolut’s UK Banking Licence Journey Chris Hill from Fox Williams and
Insights · Feb 2024Rise & Shine: Expert Tips for Fintechs Navigating AI RegulationIn a packed room at last week’s Rise & Shine event, the spotlight was on the future of AI regulation, unravelling strategies for Fintechs to futureproof their approach by learning how to cultivate trust and manage risk in what is relatively unchartered territory. Douglas Mackenzie, an expert moderator from FF News | Fintech Finance, skillfully

Sales5 insights

Develop an AI-Enabled Revenue Engine: Marketing, Sales and Customer Success
Insights · Aug 2026Develop an AI-Enabled Revenue Engine: Marketing, Sales and Customer SuccessFor most fintechs, AI still lives in the content bucket. The firms pulling ahead are the ones pointing it at the commercial machinery – and connecting marketing, sales and customer success into one engine.By Calypso HarlandFeaturing Sheila Mitham, Inbound Fintech
Insights · Aug 2026The Snowball Effect: Why Your B2B Lead Gen Is Failing, and How to Fix It on a BudgetYour pipeline isn’t stagnant because you’re spending too little. It’s stagnant because you’re making it all about you. Here’s how to build trust at scale without burning cash.By Calypso HarlandFeaturing Michael Lovegrove, Snowballn
Igniting the Engine: AI-Powered Outbound Sales
Insights · Mar 2026Igniting the Engine: AI-Powered Outbound SalesFor B2B Fintech founders and commercial leaders, the transition from "founder-led sales" to a scalable outbound motion is typically where growth stagnates.By Calypso HarlandFeaturing Michael Lovegrove, Snowballn
The Art of the "Small Yes": Turning Data into Dialogue
Insights · Mar 2026The Art of the "Small Yes": Turning Data into DialogueThere is a growing paradox in B2B Fintech growth: we have more data and automation tools than ever before, yet response rates are cratering.By Calypso HarlandFeaturing Jeremy Basset, Super Benji
Inside the "Growth Revenue Engine"
Insights · Mar 2026Inside the "Growth Revenue Engine"You can deploy the most sophisticated AI prospecting tools and craft the most psychologically brilliant relational outreach, but if your underlying operational infrastructure is fractured, you are simply pouring water into a leaky bucket.By Calypso HarlandFeaturing Sheila Mitham, Inbound FinTech

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