Professional Role and Company Overview
Rory Garton-Smith is the Co-Founder and Chief Technology Officer (CTO) of Checkmate, a rapidly growing fintech startup headquartered in New York City. Checkmate was founded in late 2021 by Rory alongside Harry Dixon (CEO) and Elliot Rampono. The company launched its flagship product, an automatic savings app primarily targeting Gen-Z online shoppers, in October 2022.
The app integrates an iPhone extension via Safari to aggregate and apply discount codes, surfacing optimized deals and providing live order updates and package tracking across 40,000+ online stores. It leverages machine learning and natural language processing to analyze users’ emails and browsing behavior to deliver personalized, timely promotions. Checkmate reportedly saves its users up to 2x more than competitors by combining publicly found deals, email-extracted codes, and exclusive brand partnerships.
Checkmate monetizes through an affiliate revenue model, earning between 1% and 7% commission on sales generated through the platform. The startup supports over 50,000 brands and partners with approximately 350 brands, including major retailers like Sephora, Walmart, Crocs, Ulta Beauty, Converse, and Macy’s.
Company Growth and Market Position
- As of mid-2023, Checkmate had surpassed 400,000 users, with around 60,000 daily active users.
- Its social media presence is significant, boasting over 600,000 followers combined on TikTok and Instagram, driving considerable organic user acquisition.
- The startup achieved the No. 1 rank in the Apple App Store by the end of 2022.
- In May 2023, Checkmate raised a $15 million Series A funding round led by Google Ventures (GV), following a $5 million seed round announced in September 2022.
- The investor consortium includes celebrity investors (Paris Hilton, The Chainsmokers via Mantis VC) and strategic venture funds such as Wischoff Ventures and DST Global.
The company is currently in its growth stage, with plans to scale hiring, deepen influencer product partnerships, and evolve the app towards a comprehensive, personalized shopping assistant aimed at revolutionizing online retail marketing.
Rory Garton-Smith's Professional Background and Education
- Rory holds a double degree in Law and Engineering and completed a Master of Data Science at The University of Western Australia.
- Prior to Checkmate, he worked as an Engineering Project Manager at Apple (2020–2022), focusing on iPhone-related projects and iOS extensions, providing him relevant domain expertise for the development of Checkmate’s Safari extension.
- Rory also has experience in various law and engineering roles, showcasing a diverse skill set with a unique combination of technical, legal, and managerial competencies.
- He was formerly active in the music industry under the moniker "Elk Road" before transitioning to full-time technology and entrepreneurship.
Leadership and Personal Attributes Related to Business
- As CTO, Rory drives Checkmate’s product development and technological innovation, particularly emphasizing privacy-conscious, user-friendly design that balances merchant marketing effectiveness with consumer data security.
- He has articulated a vision to transform how online store marketing operates, aspiring to establish Checkmate as the marketing platform for large online retailers within the next two years.
- Rory has publicly acknowledged the intense pressures of startup leadership, including experiencing anxiety and panic attacks amid Checkmate’s rapid growth, highlighting a personal commitment to resilience and adaptability.
- The rapid user adoption and high-profile investor interest suggest strong validation of Rory’s technical and strategic leadership.
Company Culture and Team Development
- As of early 2025, Checkmate has expanded considerably, transitioning into a growth-stage company with a significantly enlarged team comprising diverse talent.
- The leadership team is actively cultivating strategic board-level additions, including GV partner Frederique Dame, to deepen institutional support.
Summary: Rory Garton-Smith combines a rare blend of technical leadership, engineering experience at Apple, and legal/business education to lead Checkmate’s technical agenda. Checkmate is a high-growth fintech startup with strong institutional backing and a disruptive product that personalizes online shopping savings while addressing critical gaps in e-commerce marketing caused by evolving privacy regulations and user behavior. Rory’s hands-on product innovation, strategic vision for marketing platform transformation, and experience with scalable app development position Checkmate well for continued expansion and industry impact.
