“People don't just bring part of themselves to work. They bring their whole selves.”
About SKIP
SKIP is one of Canada's leading food delivery platforms, with approximately 1,200 employees across the country. With major hubs in Winnipeg and Toronto, SKIP has grown rapidly while maintaining a strong, people-first culture.
Seeing the Whole Person
As Head of HR, Cailey Brown has spent eight years shaping SKIP's people strategy.
A core belief drives her approach:
“People don't just bring a part of themselves to work. They bring their whole selves.”
That philosophy influences how SKIP designs its benefits. The team intentionally evaluates support through the lens of life stages, asking not just what employees need today, but what they will need tomorrow.
Caregiving is one of those moments.
It is often invisible until it is urgent.
The Forgotten Life Stage
Across the workforce, caregiving shows up in quiet but significant ways.
Resume gaps from candidates who stepped away to care for a parent.
Colleagues navigating the financial and emotional strain of finding care.
Employees managing aging parents without a plan in place.
“You don't want to be put in a position where you didn't have a plan and now you're trying to be reactive.”
Elder care is not a fringe issue. It is a growing reality. Yet historically, it has been underrepresented in benefits design.
For SKIP, that gap mattered.
Closing the Gap
As the HR team revisited its broader benefits strategy, mapping offerings against life stages, Kindly stood out immediately.
“It really fit into our philosophy around benefits and how we support people through every life stage.”
This was not about adding another perk. It was about addressing something employees may not even think to ask for until it becomes overwhelming.
“I think this is one that is often forgotten. And Kindly is closing that gap.”
There was also a values alignment. As a proudly Canadian company, SKIP was drawn to partnering with a homegrown Canadian platform focused on solving a uniquely pressing issue for Canadian families.
Kindly will be announced at SKIP's all hands meeting and rolled out company wide shortly after.
Why It Matters
For SKIP, this is both a human and business decision.
“Anytime we bring in a new benefit that makes someone feel valued, we're going to see that return.”
Cailey sees impact in three areas:
Retention
The cost of turnover is significant. When employees feel supported through life's pressures, they stay.
Engagement
When people feel seen as whole individuals, not just numbers on a spreadsheet, their connection to the organization deepens.
Mental health
“There are pressures everywhere,” Cailey explains. “Having a targeted resource that supports people through elder care is really important.”
Perhaps most importantly, this signals something proactive.
“We're thinking one step ahead. We're closing a gap before people even have to ask.”
At SKIP, supporting employees through every life stage is not reactive. It is intentional.
And that intention compounds over time.