The Global VC

Pineapple Turns CVs into Instagram-Like Stories to Make them More Engaging

How can a personality shine through a CV? For Gen Zs raised on Instagram and TikTok, a LinkedIn-style resume might not be the preferred way to stand out.

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Tim Chae

Tim Chae

Managing Partner





How can a personality shine through a CV? For Gen Zs raised on Instagram and TikTok, a LinkedIn-style resume might not be the preferred way to stand out. Enter Dublin-based Pineapple. The company is essentially applying social media tactics to the world of hiring, by allowing candidates to create engaging visual “stories” that can appeal to employers. 

The Nuts & Bolts 

Problem: For many small businesses, hiring staff is often touted as one of their biggest challenges, because they have to comb through hundreds or thousands of CVs that offer little insight into a candidate’s personality. And for many of those businesses, personality is often more important than credentials.

Solution: Pineapple aims to solve these challenges. The candidate’s CV looks similar to Instagram Stories, where users can put together a running stream of photos and videos. They are easy for job seekers to produce and allow businesses to potentially filter through applicants more quickly than traditional CVs or video applications. 

Employers can also create visual job posts to portray their brand, and communicate with candidates directly through the app. Businesses can provide a Pineapple URL through their social channels, website, or even other job boards.

Getting to Know Pineapple

Pineapple co-founder and CEO David Diamond is a designer who, at age 14, convinced Des Traynor, the co-founder and Chief Strategy Officer of Intercom (a 500 portfolio company), to hire him as an intern. His stint turned into a full time job after high school graduation, but David spotted an opportunity when chatting with his friend and Dublin café owner Oliver Cruise about the challenge of hiring staff. Together with a third friend and restaurant owner, Phil Martin, the trio launched Pineapple.

Why Now?

Gen Z is known for communicating with images and being active on social media. As this generation is starting to enter the workforce, businesses need to cater to their preferences in order to attract the best candidates. Those that have to fill positions fast can provide their Pineapple URL and direct candidates to Pineapple to apply, which helps in filtering. 

Future of Pineapple 

The team plans to continue developing new features, especially for larger businesses and expand into new markets. 

You can learn more about Pineapple at

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Tim Chae

Tim Chae

Managing Partner

Tim is a General Partner at 500 Global and manages 500's San Francisco-based global fund, investments, and accelerator program. Among his investments include Spoon, OP.GG, PeopleFund, More Labs, Rachio, Dano, and Famebit (acquired by Google). In 2016, he was named to the Forbes Asia's inaugural '30 Under 30" in Finance and Venture Capital. Continuing his career in VC, Tim became one of the youngest GPs at the age of 23 in 2015 with the closing of $15M South Korea-based fund, 500 Kimchi, L.P. Prior to 500, Tim founded several bootstrapped and venture-backed startups, including PostRocket which provided Facebook newsfeed optimization for brands and took part in Batch 3 of 500’s Seed Accelerator program. As an entrepreneur, Tim was named one of the top Youth Entrepreneurs in US by NFIB and McKelvey Foundation, and almost simultaneously, also became one of the youngest VCs at the age of 19, as an Associate at a seed-stage micro-VC firm in Boston.