During the digital era, India witnessed a shift in companies’ work culture, which amplified when COVID-19 hit the country. Organizations started to work remotely and experienced the numerous benefits it brought. The comfort of working from home was greater for digital businesses whose significant operations could be performed online. However, is it really that productive for digital companies to telecommute? The case illustrates how a digital company, Career Pandit, formed in 2018, unfurls and expands its business and further highlights the challenges the pandemic raised concerning people management. In addition to the discussion, the purpose of the case is to determine the implication of workplace flexibility and moonlighting and how Indian startups cope with the uncertain future challenges it brings.