Eileen O’Mara has a knack for picking winners - now the Chief Revenue Officer at fintech company Stripe, the Irish-American tech leader has forged a career working at some of the most dynamic, founder-led tech companies in the game including Oracle, Salesforce, and now Stripe. 

Reputationally, Stripe is known for their high standards, fast-moving pace, and obsessive and relentless focus on the needs of their users. In this insight dense episode, Eileen discusses how Stripe keeps user “asks and feedback” at the heart of what the company build, how to thrive as an introverted leader in tech, and her prediction that usage-based billing as a pricing model is set to unseat the dominance of the subscription-based billing era for AI and content companies in particular.

This week's guest is the incredible author Diana Reid, whose new novel Signs of Damage is coming out on March 4th 2025.

Signs of Damage is Diana’s third novel published by Ultimo Press, and comes off the back of the success of her first two books Love & Virtue and Seeing Other People. The plot is inspired by the notion of “terrible things happening in beautiful places” (think White Lotus, The Beach), otherwise known as the genre “summer noir."

Dialling in via Zoom from London, Diana breaks down her writing process, talks how to build a literary career after first getting published, and goes into what it means to get comfortable with the fact that embracing a creative career versus locking into corporate life means embracing a life path that is inherently non-linear.

This was a special conversation for Tash, who remembers being at uni with Diana doing a skit show called Law Revue together, and being blown away by her writing chops all the way back in 2015.

Here’s Diana Reid.

In the heart of Haymarket in Sydney’s CBD, a group of 110 engineers and bankers are building a new company that simplifies how banks operate.

At the helm of this operation, which is called Constantinople after the Roman Empire, is a formidable woman called Di Challenor. Never being the one to tell herself no, Di and her co-founder Mac Duncan hold a unique title in Australian business history as the duo to raise the largest ever seed round for Constantinople – $32 million.

So what went into the making of this founder? In this episode, Di Challenor sits down with Natasha Gillezeau to talk about life growing up as the daughter of a mining executive, which meant regularly moving schools and always being the 'new girl', how to raise capital, and the sheer power of never giving up.

Ten years into building health and fitness company Kic, Laura Henshaw and her co-founder Steph Miller (née Steph Claire Smith) have survived the initial years of startup life. Now, she’s ready to set the company up for success well into the future.

Laura sat down with Natasha Gillezeau to talk about how she’s scaled the Kic team, the importance of navigating differing communication and work styles with a co-founder, and the guarding the ‘soul’ of Kic when tempting short term offers are on the table.

From rural Montana to a tech unicorn, Emily Glassberg Sands breaks down her journey into data science and how other women can embrace similar opportunities in technology.