Leanna Di Benedetto

Leanna Di Benedetto is in the business of fun. After graduating from Radio and Television Arts (RTA), she worked on Canadian Idol and Deal or No Deal before taking off to travel the world. Leanna spent eight years abroad backpacking around Europe and working in Australia in Digital Media as a Digital Producer and Project Manager. How’s that for a career journey?!

Now, Leanna’s back in Canada and chose Points as her home away from home. It was love at first interview where she was drawn to Points’ team atmosphere and culture. Leanna wears two important hats – Scrum Master and Social Committee Chair.

What do you enjoy most about working at Points?

One thing that stood out over other job opportunities was the culture at Points. It’s relaxed and very much a team atmosphere. Many companies claim to be a team atmosphere with social aspects but I found this to be genuine at Points. They care a lot about people.

Tell us about your day to day role.

I’m the Scrum Master for our BGT (Buy, Gift, Transfer) and Infrastructure teams. Like many other software development and technology companies, we work in a methodology called Agile. In my role, I host daily team stand-up meetings, I plan for the next sprint or quarter, and do a retrospective where we look back at things we did well or things we could’ve done better. At any given time, you’ll either find me in a meeting, with my head down planning, or making sure my team is ready for our next push and feeling supported.

What was your path to becoming a Scrum Master?

It happened organically. My background is actually in Television and Radio. I’m a Ryerson graduate from the RTA program. After school, I bought a one-way ticket to London to spend time traveling. I serendipitously landed in Sydney, Australia, where I found my passion for project management. After working a series of roles for a TV network, I ended up as a Digital Producer, where I was managing major projects. I enjoyed it so much that I got my certification as a Scrum Master, became a Project Manager and as they say, the rest is history.

You’re also the head of Points’ Social Committee. What is the Social Committee?

Just as it sounds – a committee of staff who want to have fun at Points. We’re a group about 15 people who create all kinds of fun activities throughout the year. Our events are funded by the earnings of our weekly refreshment cart 50/50 draws and the raffle at our annual holiday party. We plan events to celebrate Halloween, Thanksgiving, St. Patty’s day and other less-traditional festivities like Pi Day.

How do you manage that on top of being a Scrum Master?!

It is almost like a second job at times! I volunteered to be the chair and it’s a fun position. I think it helps having a project management background to take on the role. It’s often about chasing people, getting ready for fun events, making sure everyone has what they need, and managing our social committee budget.

What are your favourite social committee events?

So far, I’ve really liked our Bake Off and the “Are You Smarter Than a Pointster?” events  – I helped run that one, so I’m pretty biased. Those have been my favourite ones, but many more to come!

What are some activities that Pointsters can look forward to in the near future?

We are just a few weeks away from our annual May Wellness Month, which is a month-long challenge to be fit, active and healthy. In previous years, we’ve armed participants with Fitbits to track their activity, and awarded individual and team prizes for the winners…which included extra vacation days! We had lunchtime yoga and kickboxing sessions. We set up a juice bar, had weekly walking groups, played games in the park, and set up lunch and learn sessions about managing your work style to reduce stress, and tips on relaxing the body and mind. I can’t give away too many secrets, so you’ll have to follow along on our social media channels to see what we’ve got planned.

We also have lots of great Points For Good events coming up, including Day of Pink, Bike Ride for the Heart and Stroke Foundation, Blood Donor Clinics, and Habitat for Humanity Build Day.

Summer Fun!

And, if Leanna’s insights aren’t enough reason to get excited about Points events, we’re also a few months away from Summer Fun. This is our version of a company summer picnic that lasts for two whole months. Learn more about it here.


Now that you’ve gotten to know one of our incredible Pointsters, how about becoming our next one? Browse our open jobs here.