Leading Women in Singapore’s HR Tech Scene

[guestpost]This post is done in collaboration with Entrepreneur Organisation.[/guestpost]

Recently, we have seen HR tech evolving very quickly and with nimble startups innovating, they have pushed larger enterprises to adopt innovative HR technologies.

Companies have been leveraging on and even acquiring HR tech vendors that are driving positive change in the world of work.

We’ve had the honour of speaking with three leading women in Singapore’s HR tech scene to access their insights and experiences.


Chelsea Sim, CEO & Co-Founder, Botbot.AI

How would you describe your business? 

Botbot.AI is an enterprise productivity tool that uses conversational interfaces to automate business processes and workflows.

By using chat as an interface, businesses can make the most of their existing enterprise software.

Similar to scaling a company, we build specialist chatbots that take over narrow functions and become excellent at doing those, then multiply that across various workflows within organisations.

The result of it is that your rainmakers or key decision makers can now be supported by one back-office staff operating multiple efficient and effective chatbots, rather than hire more people just to handle the menial, transactional and repetitive work, as is common practice nowadays.

In doing so, we hope to tackle the underlying problem of underemployment in the region.

Are there any specific role models that you look up to in the course of your journey? What made this person fall onto your role model list?

I look up to role models a lot, actually — I’m a huge history buff so it has ranged from Genghis Khan to Wu Zetian to even the goddess Athena!

At the moment, one of my greatest role models would be Michael J. Sandel, an American political philosopher.

Other than the clarity and eloquence with which he examines the political systems and economic markets of today, his Socratic discursive approach to many of the most difficult issues in the world today (such as equality) gives me an avenue from which I can learn to have these same conversations at work, and hopefully one day, through this, transform the way work is done in our time and age.

What are you bad at doing professionally, and how do you practise circumventing that in the course of your work?

When it comes to thinking in systems, I can safely say I’m rarely the brightest bulb in the room.

Thankfully I’ve surrounded myself with talents who are incredible at doing this! At the end of the day, we can’t be everything in business.

That’s why business is a team game — you have your own strengths and you leverage that to build up others around you.

I’m very fortunate to have found others with strengths that complement my weaknesses, and as a team, we manage these gaps in knowledge, experience or skill together.

As I’ve found, you don’t even need to be an exceedingly good team player to tap on this — you just need a humility, hunger and tenacity in finding new learning approaches for complex subjects, one that’s tailored to and works for you.

What’s a song or poem you’ve been addicted to recently?

I’ve been listening closely to Roots Before Branches by Room for Two — it’s a song that reminds me of my very first convictions in the most painful teething stages of growth.

Poetry by David Whyte has always been a consolation for me when, as it tends to be in startup journeys, clarity is lacking.

Recently, the poem Sweet Darkness has resonated a lot with me — it’s comforting how it brings alignment and coherence between the quiet of night and chaos of the day.

What is a maxim you live by and why?

Balance is a concept that is very foreign to me — in fact, people tend to say I am “intense”, but one maxim I always try to balance is ‘minimum effort for maximum impact’.

Imagine these two factors converging on a single point — where is that point? Some say it’s being lazy, but I believe past a certain point, effort doesn’t result in more impact, and if so, effort should be redirected to other areas of impact.

So in life, in work, and even in relationships, I constantly strive for and seek out this convergence.

Maybe sometimes a little too intensely.

In the last 12 months, what new belief, behaviour, or habit has most improved your life?

Lately, the conviction that we should scale only when it needs to has been golden.

Many businesses die out because they are focused on the operational processes and scaling when they haven’t even begun to figure out product-market fit or customer demographics yet!

I make it a point to scale only if it has been shown to require scaling, such as if it a certain workflow tedious and we foresee that it will come back frequently in the coming months.

What are one to three books that have greatly influenced your life?

Justice by Michael J Sandel was crucial in my formation of thought around the central question, “What is the right thing to do?”

Is doing the right thing the same as doing what is fair? Fair for who, anyway?

It was a great primer to philosophy for me, and today the influence of this book can most prominently be seen in the number of drafts I have around performance management systems and total rewards management today, though I haven’t found a system that’s a perfect fit for the organization yet!

Conversations with Lee Kuan Yew by Tom Plate was also highly impactful in my adoption of pragmatism as a general approach to business decisions.

Witnessing how our founding father made pragmatic decisions that ultimately never sat well with any particular political affiliation but still gave us good governance was a lesson in itself, and some of his advice around dealing with hecklers and indecision still remain close to heart today.

What’s one productivity hack you can’t live without? 

I’ve been journaling very regularly since I was 10, and since then, I’ve noticed that my writing more resembles philosophical ramblings than diary entries!

Writing (in any form, be it prose, poetry or plays) brings clarity and coherence to life and gives me a distance through which I can examine issues closely, from neutral grounds.

Over time, writing has become less of a habit than it has been a way for me to make sense of the core issues that underscore many symptomatic problems I face day-to-day.

I’ve also found that intermittent fasting does a lot for focus! I have never been a foodie so that has helped me get into the habit much faster.

I usually only have dinner and/or lunch, which means that my energy throughout the day isn’t susceptible to food comas or sugar highs.

I never particularly enjoyed eating clean, so I still look forward to hearty (but not unhealthy) meals at the end of every day!

Do you follow a certain morning routine or daily schedule to maximise productivity and well-being? 

I was introduced to the concept of energy management very early on in my career, and after copious iterations, I’ve finally found something that works!

I do have a ‘morning’ schedule — in fact, very early. My days are mostly kept for meeting other people, and my evenings are reserved for family — that leaves the twilight hours for work.

My energy begins to surge at 12:00 AM and I’m often awake till 5:00 AM and the best of my work has mostly come from these hours when I’m most lucid and alive.


Dorothy Yiu, COO & Co-Founder, EngageRocket

Tell me more about yourself.

I co-founded EngageRocket in 2016 with the aim to use people analytics to create better workplaces and happier employees.

At EngageRocket, I lead product design, development, technology and customer success.

Previously, I served as Head of Operations for Gallup (South East Asia) and oversaw the execution of large-scale consulting projects for clients in Singapore, Malaysia, Indonesia, Philippines, Vietnam, Hong Kong, Australia and Dubai.

How would you describe your business?

EngageRocket is a people analytics software that collects and analyses employee sentiment and feedback in real-time and provide insights to leaders, HR and people managers so that they can help their employees belong, grow and perform with the company.

We are simple to use and we automate all the administration and analytics behind the feedback collected.

The main value add is the easy-to-understand insights we present HR, leaders or managers so that can make the best people decisions.

What is your proudest moment in the history of your business?

It was when we closed our very first full-paying customer back in 2016.

All the accounts before that were either on our MVP or were on heavily discounted trials.

It was a particularly proud moment for us because not only was the first customer a reputable company, they had called us 5 mins after giving us the sign-off to increase their subscription from 1 year to 2 years!

What are one to three books that have greatly influenced your life?

  • On leadership — True North by Bill George
  • On negotiation — Never split the difference by Chris Voss
  • On entrepreneurship — The hard thing about hard things by Ben Horowitz

In the last 12 months, what new belief, behaviour, or habit has most improved your life?

Since the start of 2019, I have adopted a new habit of setting ‘Topic of the month’ for myself.

January’s topic was ‘Tableau and Data Analytics’ and February’s was ‘Gender equality’.

I realised after a hectic 2018 that the chaos of my day to day responsibilities have led to a lack of an intentional structured approach to broadening my knowledge.

My readings throughout the year were very unfocused and so, ‘Topic of the month’ is my way of intentionally researching and reading up more on a chosen topic.

What is a maxim you live by and why?

Be authentic.

For a purely practical reason, it takes way too much energy to pretend to be someone you are not.

As a co-founder of an early-stage startup who is still very much involved in both strategic and operational aspects of the business, I need all the energy I can to get the best out of every day.

I also enjoy building meaningful relationships with people and there is absolutely no way to build a true connection with someone else without being one’s true self.

What is your business superpower and how do you use it daily?

Anyone who has worked with me would know that I am obsessed about getting things done.

I’m all about being effectively efficient. I have the ability to very quickly see what the most critical thing needs to be done in any given situation and effectively mobilise the necessary resources to execute on it.

All while putting in place a plan to ensure the rest of the less crucial tasks are taken care of at the same time.

My husband jokes that my mind is like google maps, give me a goal or vision and I’ll give you the best route to get there. Coincidentally, I am also quite good with road directions!


Sharon Lee, COO & Co-Founder, HReasily

Tell me more about yourself.

I am a Chartered Accountant and spent the greater part of my career in commercial & corporate finance and business advisory.

I have held C-level Finance and Operations roles, working in companies like KPMG, General Electric and TELUS International.

As a Co-Founder & COO of HReasily, I oversee Finance, Customer Success and Operations of our company.

As a start-up moving to a scale up operations, every day is the start of a new adventure.

How would you describe your business?

HReasily is a cloud-based HR Tech company that provides businesses with a digital platform to manage their HR processes.

Our SaaS platform helps the business of all sizes manage payroll, leave, claim, employee records, and time attendance.

We are also integrated with banks, accounting software and e-payment platforms to provide more seamless integration for our customers.

Today, HReasily is localised in seven countries with more countries in the roadmap.

What is your proudest moment in the history of your business?

One of the key milestones for HReasily that we continue to celebrate until today is the establishment of our partnership with UOB regionally.

In the early stage of our business, it was important to garner the endorsement of a well-established brand like UOB in the region.

It was a validation of our value proposition to the business community that our software aims to deliver real value to manage age-old challenges of managing payroll.

Our partnership has allowed us to ride on their distribution network to reach out to the small business within the UOB business banking community who are the greatest beneficiaries of these affordable and integrated solutions.

UOB’s commitment to support our regional expansion has also led us to continue to innovate and introduce new capabilities to SMEs in the SEA region.

How has a failure, or apparent failure (during this/prior business), set you up for later success?

Starting and scaling a company requires a lot of time, energy and financial resources.

The co-founders always remember our darkest moments where we had very little resources, tonnes of projects to be completed and little assurance that the business concept could materialise.

From the start, the team already had big plans and we constantly push ourselves beyond comfortable boundaries to make this happen.

Lending mutual support gave us the faith to push on strongly.

While we are far from the end of our journey, our tenacity, pure diligence and single-minded goal to make this happen to help us through our little successes along the way.

Do you follow a certain morning routine or daily schedule to maximise productivity and well-being?

My day starts early in the morning before anyone is up.

The quiet time allows me to prioritize my day and plan the main deliverables to be accomplished.

Breakfast is the meal that our whole family sits down together, catch up and bond, even if it is only 10 minutes per day.

This is a great way to start my day.

This simple routine allows me to tune to work mode and prepare myself for rigours of the day; meetings, office emergencies and client engagements.

What are one to three books that have greatly influenced your life? 

  • Leading by Alex Ferguson
  • Scaling Up by Verne Harnish

What is a maxim you live by and why?

Seize the day!

I have two daughters and have this great opportunity to inspire them with what I do and allow them to journey with me through our startup highs and lows and importantly, Make It Happen on a daily basis.

Likewise, being a sounding board and a role model for young women continues to inspire me.

What is your business superpower and how do you use it daily?

Making things work.

I run the operations of HReasily and one of the key challenges we constantly face as we scale our business is the ability to identify critical paths, the structure for success and get teams to collaborate with each other to reach our common goal.

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