Dylan Cunniffe

Senior Product Manager

Building at the intersection of AI, platform and user experience. Based in Cape Town.

Dylan Cunniffe

About

I'm a Senior Product Manager based in Cape Town, currently at TurnStay โ€” a VC-backed seed-stage startup building multi-currency, cross-border payment infrastructure for the travel industry. I joined as the founding PM, working directly with the founders on product strategy, go-to-market, and standing up the internal tooling to make the company run.

Before TurnStay, I spent nearly five years at Prodigy Finance, a Series C fintech providing international student loans. I started as a Junior PM and grew into leading two domains: Customer Platform (authentication, comms, support infrastructure) and Verify & Disburse (KYC, AML, loan fulfilment). The work ranged from migrating core authentication systems to shipping AI-powered tools for document verification and complaint detection โ€” a few of which you can read about below.

My background sits somewhere between product, data and engineering. I studied Economics at UCT, taught myself Python and SQL along the way, and have always been drawn to the messy, interesting problems at the intersection of business logic and technical systems โ€” especially where automation and AI can do the heavy lifting.

Outside of work: avid gamer, tech enthusiast, and always happiest somewhere outdoors.

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Portfolio

AI Document Verifier AI ยท Automation
50% reduction in manual document verification

Manual document review was a significant bottleneck in Prodigy's KYC process โ€” labour-intensive, error-prone and difficult to scale. Working closely with the Data Science team, I led the product development of a multi-agent AI verifier capable of reviewing uploaded documents, cross-referencing data and flagging exceptions for human review.

The result was a 50% cut in manual verification workload, faster customer onboarding, and a more consistent, auditable review process.

Multi-agent AI KYC / AML Data Science collaboration
UK Direct Disbursal Growth ยท Fulfilment
61% increase in UK average loan size

Prodigy's UK market was underperforming relative to its potential. Research revealed that the existing disbursement flow was a barrier to higher-value loans โ€” funds were routed through university finance offices rather than directly to students, creating friction and limiting the addressable loan amount.

I led the design and launch of a direct-to-customer disbursal feature that bypassed this constraint. The result was a 61% increase in average UK loan size and a meaningful gain in market share in non-US markets.

Fulfilment Market Expansion Payment Flows

Skills & Tools

Product Tooling
Heap Metabase Hightouch Tableau JIRA Zendesk Miro Intercom Attio n8n
Data & Dev
SQL Python API Design Reverse ETL Process Automation
Core Strengths
Platform Strategy Experimentation AI & Automation Internal Tools OKRs JTBD Roadmapping