Xero’s story demonstrates how a smaller brand can close the gap with bigger rivals by investing in memorably humorous and empathetic advertising. After 10 years in the UK’s business accounting software market, New Zealand’s Xero brand had relatively low awareness and consideration. By investing in broad reach media and emphasising its Kiwi-ness by using a performer from cult NZ comedy ‘Flight of the Conchords’ in its advertising, Xero increased awareness, appeal, and trustworthiness. This case includes evidence that branding and commercial goals were exceeded, helping return an estimated long-term gross profit of £4.07 for each £1 invested in marketing.