Learning outcomes The learning outcomes of this case study are as follows: Students will be able to comprehend and visualize the initial hiccups and operational hurdles faced by digital start-ups in an emerging market. Students will be able to evaluate the importance of digital marketing for promoting start-ups dealing with sustainable products in the service industry, thereby helping them to develop digital marketing strategies to organically promote a service. Students will be able to perform strategic positioning of a start-up based on perceptual mapping methodology. Students will be able to identify the various aspects for identifying and creating a viable business model. Students will be able to use Osterwalder’s business model canvas for identifying the important operational aspects of the start-up. Students will be able to visualize the entrepreneurial challenges in an emerging market. Case overview/synopsis This case study highlights the dilemma the protagonist, Prerna Prasad, faced in her travel start-up venture, Ecoplore. Ecoplore is an aggregator platform that onboards only eco-hotels. To the best of the authors’ knowledge, Ecoplore is India’s only platform that promotes and onboards only those hotels made up of mud, wood, bamboo, stone or any local architecture and that maintain at least 30% green space on their premises. Ecoplore has been recognized by the United Nations Environment Program for fulfilling Sustainable Development Goal 12 and has also been bestowed with the Gold Award by Indian Responsible Tourism Awards 2019. Prasad had already identified her target market. Prasad took conscious steps towards reaching her target audience, and her first step towards that was designing Ecoplore’s website. Being aware of the importance of content marketing, Ecoplore’s content was curated with fresh and quality write-ups, pictures, blog posts, etc. Ecoplore’s website was also optimized for mobile and desktop versions to deliver a great user experience. Features like easy navigation and the website's speed were also taken care of. Being active on social media platforms, Prasad made sure that the pages of Ecoplore across various social media platforms were well connected with her website. Despite doing so much, it was found that the number of visitors was few after a span of two years. Conversion on the website was low, which ultimately affected the return on investment. Prasad was befuddled as to why the conversions were low despite having a great website that was considered a window to the organization. She faced the challenge of reaching her target audience despite being present online. Upon detailed analysis, Prasad found that Ecoplore was showing up in the search engine research pages (SERP) in only a few keywords, meaning the keyword density was low. Also, the website lacked backlinks, which would eventually help them to rank high on search engine optimization (SEO). This means that Ecoplore will need to revisit its SEO strategy if Prasad wants to promote her organization organically. Now, to increase visibility and ranking on SERP, Prasad had two options before her; first, she could do it organically via SEO or through search engine marketing. She was keen to build the traffic organically, knowing its long-term benefits. As a marketer, what should be Prasad’s strategy? This case study can be used for class discussion purposes for the students pursuing the courses on digital marketing, SEO and digital marketing optimization. Complexity academic level This case study is suitable for students learning the fundamentals of digital marketing (basic and advanced) course, marketing management students and digital marketing workshops. The level of difficulty is medium. The knowledge pre-requirement is marketing management. Supplementary materials Teaching notes are available for educators only. Subject code CSS 8: Marketing.