Homecoming: How KeyReply left Singapore to build chatbots for Gov.sg and SGAG

By Tasha Abdul Mutalib (@tasha_abdm)

SG Stories is a new long-form series featuring homegrown startups with unique strengths and extraordinary journeys – exclusive to Girls in Tech Singapore.

We hope you’re inspired to learn from their stories, as we did in telling them! – Tasha, Editor in Chief.


Home evokes strong emotions – for many Singaporeans so strong that they rank the National Day song of the same name as the only one that endures. It’s natural to feel a similar pride for homegrown business – but Singapore only has 2 unicorns to its name.

Why is this the case, when Singapore is consistently rated one of the best places for startups and investment?

Experts attribute this to two things: reluctance to commit, and the country itself being a bad place to fail. Founders try to burn the candle at both ends with a day job, and funding options are abundant for those who want to keep their idea alive year on year – an environment unconducive for real innovation and scale.

KeyReply COO Carylyne Chan and her co-founders chose to leave all this behind, and strike out on their own – in the meanest playing field of all: San Francisco, right next to the giants of Silicon Valley.

KeyReply is an AI chat automation platform for businesses to engage customers via websites, SMS, mobile apps and more. Featured as a Facebook Messenger Platform Development Provider, KeyReply is responsible for SGAG’s Singlish-fluent bot that shows you the “most solid” memes and takes submissions in real-time.

The KeyReply team was formed when CEO Spencer Yang connected COO Carylyne and CTO Max Xu, both of whom he knew separately. Max had just won the 2014 Facebook Singapore Hackathon (which he went on to win the next year as well) – his idea for a collaborative team canvas became their first project together, which they called GraphPaper for its grid-like canvas. It was also the team’s first failure, and the birth of KeyReply.

“Ultimately, the GraphPaper product didn’t really get much traction – which, in hindsight, I totally understand why – but we realised through that customer discovery process the need for better and faster customer support. KeyReply was born to solve some of these challenges, first as a keyboard, and now as a chat automation solution,” Carylyne elaborated.

It was also the impetus for their entrepreneurial journey. As GraphPaper was failing in 2015, the team received an invitation to a top-rated accelerator program in the US. “We didn’t hesitate and immediately jumped on a plane to the US to continue building KeyReply there,” Carylyne said.

The decision to join AngelPad seemed like a no-brainer – it’s ranked the #1 U.S. Accelerator by MIT and this year tied with Y Combinator in the “Seed Accelerator Rankings Project” (SARP), an annual benchmarking study run by Entrepreneurship and Management experts from Rice University, MIT and the University of Richmond.

The team had their own special set of problems though, as Carylyne described: “Many of the challenges centered around building networks and assimilating into an environment where we didn’t know anyone. In a place where people know others they’d gone to school with, or through connections from other activities, we had to fight our way into understanding the landscape and culture while building the business to a global standard and scale.”

San Francisco also proved difficult financially; at one point the team stuffed themselves into a one-bedroom apartment with three other founders to save money. “We eventually got evicted due to fire safety laws when the landlord found out – it was pretty epic,” she said.

The team gained a new outlook on learning as you go: “As startup founders, being scrappy can be a real virtue as you eschew everything that other people have to rely on, like getting agencies to run your ads or do your social media marketing, or getting someone else to do this and that for you. You

learn to do everything by yourself, and that can be challenging but rewarding at the same time.”

Carylyne credits good communication and collaboration for keeping the team focused. “Having gone through a lot together, we tend to view challenges as another problem to solve, and will methodically discuss and work through them. I think this is an imperative part of building a team, in finding other team members who know and care about you even when everything else might be tearing apart at the seams.”

Despite their resilience there are still issues to contend with. Carylyne admits, “Of course, at times, there can be personal difficulties that we have to confront, such as self-doubt or finances.

Many times, going into a big pitch or writing a blockbuster content piece, I wonder if I’m qualified enough to do that – classic imposter syndrome style. Ultimately you just have to concentrate on the outcome you’re trying to achieve and ignore everything else.

As founders who hadn’t drawn salary for the longest time since we started the company, the going also gets tough for us, but having the belief (and resistance to buying things) can go a long way in managing financial issues.”

Their resolve has paid off – in November 2016 KeyReply powered the first Singapore government chatbot on Facebook Messenger.

It hit the news with coverage by Yahoo and  e27 among others – a true mark of homecoming as part of Ministry of Communication and Information (MCI) efforts to leverage on new technologies and platforms to reach out to citizens.

On KeyReply’s path to this achievement, Carylyne said: “We were thrilled to be given the opportunity to bring our government closer to our fellow Singaporeans. I believe that there will be more applications of AI that will touch the lives of citizens deeply, and our Gov.sg chatbot is a step in this direction.”

She also had this to say about starting out in Singapore: “I’ve met founders who think Singapore is a good starting point for a business. Having been in a big domestic market like the US, it became clear that unless you have a clear go-to-market strategy in the region, or build a global yet localisable product, it will be difficult to grow a business to become big enough and be worth much in the long run.”

Despite their current success, it has been a long time coming for the team, with Carylyne describing her own journey as one of starting young and eventually getting involved with the community:

“I’ve always enjoyed tech-related things as far as I can remember. I started learning HTML/CSS when I was about 8, and took part in robotics competitions when I was 12. I probably only got into the tech scene as we currently know it about 6 or 7 years ago, when I met many veterans and interned at a regional tech startup.

Since then I’ve tried lots of other unrelated roles, mostly for learning. Ultimately I still think working directly with technology is the most fun, and decided to stick with it!”

Carylyne’s role as COO of KeyReply has her working closely with everyone across the business – from product and engineering, marketing and sales, to account management and support.

“Day-to-day a lot of my work directly deals with product and engineering, the core of KeyReply’s offering as a product company. That includes planning new features, acting as architect for new R&D efforts, or just grinding through round after round of QA (quality assurance) to ensure that that version of product will work well when released.

Beyond that, I also spend a lot of time on writing quality content to help customers and other industry players understand what we do and how it can help them.”

On top of the technical aspects, Carylyne adds, ”A big part of the COO role also involves being strategic, and understanding what to do to move the company forward. Staying informed about new trends and players is an important part of that, and demarcating time to think about strategy beyond the daily hubbub is also key to making good decisions.”

This ties in with the team’s idea of success, as she puts it: “Beyond any headlines or coverage that we get for KeyReply, the most fulfillment and satisfaction for us tend to come from actually solving customer problems every day and seeing results.”

As KeyReply looks out into the next few years, they are concentrating on being a natural extension for business. “KeyReply is often one of the first touchpoints for organisations looking to adopt AI, mainly because chat automation can tangibly help customers and internal stakeholders,” Carylyne said.

“Our product analyses classify and improve existing customer support data, before turning it into a bot on the other end for customers to interact with on channels like Messenger and websites. So it actually acts as a way to diagnose ongoing customer issues and help the organisation improve its offerings.”

KeyReply is already anticipating future innovation and challenges in their space with confidence in their customer management and global testing capabilities. “In the next few years, there will no doubt be great strides forward in AI research and commercial technology. Our comprehensive product and ongoing relationships with our customers will allow us to iterate and apply new technology at scale.

Additionally, as we believe in building a global company, we are able to test new product ideas across market regions, and that will help us to validate hypotheses with more confidence,” Carylyne explained.

The team is walking the talk with analysing customer support data on a global scale. “Botdesk is a new product that we’re testing in the market to help SMBs (small and medium businesses) set up a bot under 5 minutes to answer FAQs,” Carylyne shared.

“We thought about how to distill our work on the enterprise-grade product for greater scale, and Botdesk was a way for us to quickly validate if this is something that would be useful.”

Botdesk currently offers a free 21-day trial with no credit card necessary for sign up. No coding is required to set up either – just key in your URL, customise your bot to get started, then easily retrain it using analytics on the questions asked.

Carylyne had this to say about how to iterate off current product: “A big issue with startups trying to build an AI company is that they tend to spend too much time on reinventing everything from the ground up, instead of looking for research or services that can help them to innovate faster.

There are a few things which startup founders can do to make it easier to productise their AI research efforts:

  1. Replicate and reuse research papers which are related to your use case, and try to tweak everything to see if it works for you.
  2. Find useful resources that provide either data or labels to get off the ground faster. For example, we use pretrained word embedding to help us get word meanings out of our corpora of data.
  3. Focus only on one to two areas where you really want to make it work – instead of solving general health screening, for example, you can focus on detecting lung cancer from x-rays.

If you’re a core product person, then focus on the product and assemble a pipeline of APIs or other services to make the product work. Lots of product companies have won by having superior acquisition and data instead of better technology, so having self-awareness of your strengths and weaknesses can help you make the right technology decisions to move ahead.”

As KeyReply makes further strides towards being a truly global customer-centric AI startup, it is heartening to note that they’ve given back to Singapore in more ways than one. As far as they’ve gone, they haven’t forgotten home as a place to nurture their talent and return – in order to do great things for its people.


Next week on SG Stories – brother and sister team Travis and Suzanne Chia on how they’re embracing technology to take 1-hour doorstep service Alcohol Delivery to new heights.


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