Ex-CRO of Asana Oliver Jay on how he is building business leadership talent in Singapore

Oliver Jay is on a mission to accelerate the development of senior leadership talent in Singapore. As the first Chief Revenue Officer for Asana (NYSE:ASAN) from 2016 until February 2022, Jay grew the revenue team from a few people to over 500 professionals globally. Previously, Jay had also led Dropbox’s (NASDAQ:DBX) B2B business and was Head of Asia Pacific and Latin America, making him well-acquainted with the factors that enable high-performing teams.

Today, as the CEO of Uncorked Consulting, he contributes towards the mission by coaching founders and senior executives of high-growth companies in the Asia-Pacific (APAC) region. Jay also serves as an Independent Board Director at Southeast Asia’s leading superapp company Grab (NASDAQ:GRAB), where he advises the executive team on key strategic decisions. We learn more about his perspectives on unlocking the full value of talent in Singapore.

Q: How has being in Singapore helped your various organisations achieve their goals?

A: Both Asana and Dropbox opened critical offices in Singapore because of the access to talent. Asana, for example, was able to find success in hiring 40-50 employees in Singapore to serve the APAC markets, while Grab benefits from the city-state’s strong legal and regulatory environment.

For Uncorked Consulting, I found that because of Singapore’s great momentum in encouraging entrepreneurship, there is a significant opportunity to develop the fast-growing leadership talent to scale the next generation of startups in Singapore.
 

Q: What are your views on the talent pool in Singapore?

A: When I was at Asana, I found that Singapore was simply the best place to hire talent to serve our customers in the broader Asia market. We found a very high bar for talented individuals as well as for leadership in Singapore. Singapore is the only place where we could, in one place and at scale, hire talent that could speak all the main Asian languages needed to serve our customers. Culturally, our team in Singapore had one of the highest employee engagement rates, which points to the dynamism of the startup and technology ecosystem in Singapore. The blend of local and international talent uniquely contributes to a fantastic office dynamic where everyone is always learning from each other.

Now as a coach and advisor, I have found an abundant density of high-potential talent in Singapore to support. Shortage of talent - especially at a senior leadership level - is an issue globally. In Singapore and the region, the same challenge exists. Many of the managers I have met have limited leadership experience, and this can become a bottleneck as companies seek to expand rapidly into global marketplaces. I hope to leverage my experiences as an early senior executive in multiple companies that have recently become publicly listed to accelerate the development of senior leaders in Singapore. I have confidence that the senior leadership pool in Singapore will only continue to grow and strengthen.

Q: How would you advise companies who are considering building their teams in Singapore?

A: Firstly, take advantage of what the EDB has to offer. Every entrepreneur has mentioned how helpful the EDB has been in helping them tap into the local talent market, as well as navigate the many support services provided by the Singaporean government. Secondly, get plugged into the venture network in Singapore. For a small country, the venture community and ecosystem are quite mature. The investors are well-connected and well-capitalised to help companies looking to build out their teams in Singapore.

Q: What aspects of Singapore’s business ecosystem have you benefited from as a professional?

A: At Asana, and even in a prior role at Dropbox, I oversaw the launch of 10+ offices around the world, including in countries such as the UK, Tokyo, Australia and Germany.  Building a multilingual and multicultural office was easiest in Singapore relative to all other countries. The benefit of building a team faster is that we were able to attain business traction at an accelerated rate.

I also found that the Singapore ecosystem has holistic knowledge of global business trends and customs. There is not only expertise in understanding the different approaches needed to target each of the Southeast Asian markets, but also in how to target the Chinese and Western markets. Singapore is a globalised city that is well connected to the rest of the world. This also explains how Singapore is a country that welcomes diversity at multiple levels. I have found the business ecosystem here to be very friendly, welcoming and helpful despite my being a foreigner.
 

Q: How have you and your family experienced Singapore as a city to live in?

A: My family loves Singapore. We moved from San Francisco, where we had a high bar for the quality of life…and Singapore exceeds it! We love the convenience and diversity of options for food, culture and activities. For our young children, we also highly value the plethora of high-quality education programs.