Dylan Cunniffe

Product Manager

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About me

I'm a Cape Town based Product Manager with 6+ years of experience shipping complex, high-impact solutions across platform, AI, and consumer-facing products in fintech.

I spent the bulk of my career at Prodigy Finance - where I led the establishment of the company's first platform product team, developing and integrating solutions across Identity & Access Management, Customer Support, Marketing & Communications and Data platforms. Additionally led a consumer facing domain focusing on the KYC and Loan Disbursement stage of our student loan product.

I consider myself a Product generalist. Jack of all trades. Thriving on curiosity and a passion for improving things whatever it may be. I have a degree in Economics but just as comfortable on the technical side of things - self taught coder (Python) and data analyst. I'm always eager to find ways to bring together, business, design and technology to solve problems.

Outside of work I'm an avid gamer, enjoy learning about the advancements in tech, traveling and exploring the outdoors.

At the moment, I'm on the lookout for a new PM role and excited to try something new.

Portfolio

Sentinel

At Prodigy, we treated customer support as a competitive differentiator, but a rising trend in complaints signaled a deeper issue. Our analysis revealed that most complaints were not isolated incidents. They were the result of accumulated negative interactions over time. Three consistent markers stood out: customers having to repeat themselves, the tone and sentiment of their messages, and the urgency they conveyed. Rather than solving each potential root cause, we focused on detecting when a customer was veering into this negative interaction path. Allowing us to intervene early, before frustration escalated into a formal complaint.

To address this, we built Sentinel, an AI-powered early warning system. Using Zendesk webhooks, OpenAI's API, and a custom internal service, we analyzed ticket history and context in near real-time to classify sentiment, urgency, and repetition. These insights were surfaced directly in Zendesk via a custom app, empowering agents to prioritize and escalate at-risk conversations. We rolled out Sentinel incrementally, refining our prompts with a test group before expanding to full production. Scaling to thousands of tickets daily. This not only enhanced customer experience but equipped CS leadership with early signals of broader product or process issues. Future iterations aimed to improve intervention tracking and integrate defect detection to catch product bugs earlier.