From project manager to scrum master at Woolworths

We speak to Chulanga Dassanayake to understand how he made the transition from traditional project management in a start-up to scrum master for the leading retail brand, Woolworths.

The difference between being a project manager vs. a scrum master.

Traditional project management involves a leader who makes decisions and manages a project as well as a team. He is accountable to the business for accomplishing the project objectives. The role of the scrum master is more a coaching and facilitation role (servant leader) that sits between the delivery team and the end user.

Why did you make the switch?

My goal was always to become a highly skilled project manager. I find the best way to master what I do is through building my expertise within different disciplines in the software engineering space, while working on my leadership and people management skills.

I started my software engineering career as a test analyst then moved on to become a business analyst and a project manager. I was quick enough to learn about Agile project management methodologies, and it caught my interest early on as I soon realised that Scrum would provide solutions to many burning issues in the traditional project management world. Ever since I started practicing Scrum, I have been deep diving into Agile delivery while expanding my knowledge as a Agile certified practitioner and a certified Scrum professional.  

Describe your current job as a scrum master at Woolworths (WooliesX).

Woolworths is embarking on a major expansion of its new WooliesX digital operation, which combines digital, e-commerce, data and customer services operations.

I am a scrum master at WooliesX and my role involves leading multiple squads that deliver key initiatives in Woolworth's E-Commerce fulfilment domain. Some of these initiatives includes Cloud migration activities. 

The squads led by me are working on exiting solutions that uplifts Woolworth’s technology capability to deliver best customer experience. The exposure gained in such a complex initiatives are second to none. 

Part of my role consists of actively coaching my team members, product owners and stakeholders on Agile methodologies while supporting WooliesX agile transformation initiative. I am privileged to work with a highly skilled technical team and a product management team that lives and breathes Agile values day in and day out. WooliesX is one of the best work environments I’ve worked in so far. 

Transitioning from working for a start-up to a FMCG.

I never planned for it. I was more interested in new challenges, trending technology and how I could broaden my skills by working in different industries. Every experience is a good experience, I was simply following the Deming Cycle (plan, do, check, act) and I was determined to do well in my job and provide value to the organisation I work for, regardless of its size or industry. This attitude opened new opportunities for me in order to choose the job that interests me the most.

How did you upskill? 

I have a personal goal of attending at least one professional course per year. These professional courses help me gather new knowledge and stay up to date with the industry. Up skilling yourself is a continuous process. 

Utilise all available time to learn new knowledge and never stop learning to stay up to date with the latest practices.

I also read a lot, enjoy doing my own research and teaching myself new skills. I started implementing my scrum master skills when undertaking initiatives before being sponsored by one of my employers to become a certified scrum master from the Scrum Alliance. 

What skills have helped make the career switch?

My current employer (WooliesX) was not interested in my industry-related experience. Instead, they were interested in my agile delivery experience, agile knowledge and my ability to lead scrum teams at scale.

What are some of the challenges you have encountered?

I have been faced with a number of challenges. The biggest to date has been to keep delivering key initiatives without causing outages in the production environment for key applications in the fulfilment domain. I have had to adapt to the culture while wearing multiple hats to be able to work alongside different squads as the organisation was in the process of rapid Agile Transformation. 

Level of Agile maturity is different from squad to squad, which means I can’t wait until the outcome of Agile Transformation takes effect. Instead, I help accelerate it by providing training on the fly to squads, lead them to deliver expected business value fast while contributing to the Agile Transformation activities. 

What advice would you give others looking to become a scrum master?

1. It’s important to have a career goal and stick to it

You may receive excellent career opportunities but make sure the role aligns with your career goal before you commit.

2. Embrace challenges to succeed

You will face numerous challenges and difficulties. With it, comes your Agile experience. Stay focused, adopt a collaborative approach with the teams you work with and eventually your efforts will pay off. 

3. Get the knowledge

Remember, knowledge is power so work hard to expand your knowledge while aligning your experience with your career goal. Get certified to connect the dots.


Interested in learning who leads business transformation? Read the article here.

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