e27: This is the enticing story of a dark horse who carved a niche in the startup world

Damien Cummings’s startup Peoplewave solves the problems related to on-boarding of new hires, people development and performance management

Damien Cummings, CEO and Founder of Peoplewave

He struggled with his studies and was a poor performer at school.

Although he narrowly cleared his final exams, the scores were not enough for Damien Cummings, who hailed from a lower middle-class family in Sydney, to enrol in any decent university in Australia. So, soon after finishing high school, he went straight into his first job — assuming he would be spending the rest of his life doing low-paid jobs.

“I was raised in a very simple, humble and lower middle-class environment that didn’t understand fancy business terms or even knew what entrepreneurship was. My family prized having a decent income and a steady job first. The idea of starting a business just seemed crazy and weird,” he tells e27.

Despite his poor academic performance and being bullied by the other boys at school, Cummings was a happy kid and enjoyed his life. He spent a lot of time reading books, creating things, writing and letting his imagination run wild.

“Later, I spent time learning and becoming proficient in martial arts and weapon training (I also went on to represent my country in international tournaments). Although none of these were business-oriented, looking back I can see that the social and soft skills that I acquired turned into an advantage later in my startup life,” he recalls.


McKinsey & Company was his first ever employer. Despite his poor grades, education, lack of skills and experience, he got through the interview and landed the job at the management consulting giant. This was back in 1993.

“You won’t believe that I got into McKinsey through nepotism,” he laughs. “My grandfather was a security guard in the building where McKinsey was located. Thanks to his good relationship with the hiring manager, I was hired as an office services assistant and worked there for four years. I learnt a lot from this job and also realised I would never be able to grow further without better education or connections.”

Due to desperation and lack of career options, Cummings — in his early 20s then — took a leap of faith, and together with two of his friends, launched a digital business called Dark Horizon in 1997. The company rode the wave of the dot com boom and later the bust. This experience gave him the unusual taste of freedom, pride and stress of running a startup.

“I was hooked from there. After the stress of failing the first company I became risk-averse, but I never lost the passion for running my own business,” he says.


After the failure of Dark Horizon, he went back to the corporate life and worked for several companies in his home country.

In January 2008, he received a job offer from advertising major Ogilvy in Singapore. He jumped on to the opportunity, which he thought would help him further his career. “I didn’t know much about Singapore then, as I had spent all my life in Australia. What was clear though was that the city-state offered greater opportunities for regional and global roles,” he says.

Two years later, he quit Ogilvy. He then changed his jobs several times.

And finally, in January 2017, he started Peoplewave, an employee relationship management (ERM) company in the city-state.


Having spent almost 20 years of his professional career managing people, he had seen first-hand that managers didn’t have the right skills, training or tools to manage people well. This bothered him. He realised that people leave managers, not companies, and that around 80 per cent of employees are disengaged or unhappy because of their managers.

“Managing people well has always been a passion for me, but as a manager, I was frustrated that the only tools available were the “one-on-one meetings” and the horrible “annual goals/KPIs processes” to manage the team,” he shares.

This is when he lost his job at an international bank. “It was a great job to be lost,” he sighs. “But I couldn’t imagine going back to the corporate world seeking another job. So I took that opportunity to delve back into the world of startups once again. This is when I launched Peoplewave in January 2017, and we’ve been going strong since.”


Peoplewave is a B2B HR software company. The company calls itself “Salesforce of HR”. It solves the problems related to on-boarding of new hires, people development and performance management. The startup aims to reduce the turnover, improve employee retention and make people management fairer, more transparent and data-driven.

“Over 400 businesses have signed up for our ERM platform and software. We originally targeted SMEs but in 2018 we realised that the real value we could add is to work with mid-sized and large enterprise businesses that have challenges on-boarding new hires, or face high turnover or employee retention problems,” he continues.

Cummings and team faced a hell of a lot of challenges in the initial months. “In the early days, the main focus was building great software products. We’ve had to continually improve and pivot our products to get a strong product-market fit over time,” he says. “Other than this, creating awareness was also tough, and this is something we’re still working on.”

A SaaS startup, Peoplewave charges a monthly fee or annual license fee from its clients for the service.


Despite running a successful business, Cummings still sees himself as a constant failure. He has failed badly in his relationships, as well as jobs — often striving too hard for what’s right or for the growth in environments that want status quo or conservatism.

“For me, 2018 was one of the most difficult years of my life. My brother died less than a year ago at a young age of 21. This devastated my family and left me emotionally battered. I’ve also put on too much weight through stress and emotional eating,” he says.

“Worse, we had an employee betraying our trust and allegedly embezzled our company assets and funds, and there were times we ran out of money,” he regrets. “But I’ve always managed to find the silver lining or the light at the end of the tunnel. It’s all about resilience and having a clear purpose. It helps you get through.”


During his career, Cummings also went on to secure a few certificates from high-profile universities, including Harvard.

“I am a very strong believer of continuous learning. It’s critical to stay curious, push yourself to learn new things and keep improving,” he shares. “Honestly, I wanted to do the Harvard certificate, along with similar ones from Wharton and Columbia Business School, just to appear to be impressive. Sometimes it’s things like this that make or break sales, partnership or VC deal. They are online courses and aren’t super expensive but give you an ivy league University certificate.”

“Beyond the vanity,” he continues, “I found the content very useful. Each course is a back-to-basics, which gives you a solid checklist to follow when setting up a new venture. I tend to be an ideas and people person and I’m weak at operations, so having these courses to help guide me into starting and growing a new company is practical and useful.”


Cummings also holds a Doctor of Philosophy in Management (honoris causa) from KEISIE University, South Korea.

The Peoplewave team

He’s also been awarded “Global Top 50 Digital Marketing Leaders 2016”, “Financial Services Marketer of the Year 2016”, “Digital Marketer of the Year 2016”, “Most Influential CMO 2015”, “Marketing Professional of The Year 2012” and the “Brand Leadership Award 2011”.

Peoplewave is also the winner of Singapore’s season seven Startup-O programme.

In 2017, the startup raised US$1 million in seed round, and is currently in talks for US$5 million Series A round.

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