Plooto CPO on tapping tech and mindfulness for the health of the organization

'A strategic role that a people practitioner partner can play is … working alongside the business to understand 'What specifically do we want to accomplish?''

Plooto CPO on tapping tech and mindfulness for the health of the organization

“I am a big believer that my failure moments have been really incredible learning moments, and that the acceleration of my own career journey is pretty closely tied to holding a growth mindset. Having a growth mindset and embracing failure for the really powerful learning it can bring, is maybe what I'm most proud of in my career.”

So says Chelsea Bailey, recently-appointed CPO of Toronto-based payments company Plooto. With over 20 years of HR leadership in tech spaces such as Google and X the Moonshot Company, Bailey is on the leading curve of HR innovation.

“In the organizations that I've been a part of, often in a scale-up environment, you have leaders who have a really crisp mission or vision, and they want to move fast to get there,” she told HRD Canada.

“I think a strategic role that a people practitioner partner can play is … getting really clear, working alongside the business to understand what specifically do we want to accomplish, and what types of skills and expertise might we need in order to do that? It's a fun exercise.”

Organizational health as a top priority for HR

Bailey stresses that employee wellness and organizational health are intertwined, and creating a genuine sense of belonging is a multi-pronged and essential part of that, with HR leaders in the centre of that important mission.

“It's becoming more clear that this is a crucial thing that organizations need to be considering, is the health of their culture,” she says. “More than ever, people are willing to just bail now, and go somewhere else if they don't feel that they align with the values, or they feel like they're not being genuinely taken care of.”

At Plooto there is a strong buy-in from the leadership and the board, Bailey says, in valuing the work force as the most important asset. For Bailey, that means fostering a sense of belonging, which will in turn encourage an organization’s best talent to stay.

“When I'm heard, and the organization is responsive to my needs and expresses care and concern for me as a person, I feel a greater sense of connection and belonging to that organization,” she explains.

Retention conversations as a crucial tool for employee loyalty

An strategy Bailey’s team is employing at Plooto is a focused attention on “retention conversations” – or stay interviews as they are otherwise known – as a key way to understand how individual employees feel about their roles, and what they need to do to keep them there.

“It's really a guide and a tool for managers to engage with their reports, to come to know them better individually and understand what motivates them,” says Bailey.

“So our leaders are engaged and really connecting with the team and making sure that they have a voice and know that they're valued, and that we have a strong desire to retain them at the company.”

Using people analytics has also emerged as a non-negotiable process for HR as well, Bailey says, as a crucial way to understanding the bigger picture of the workforce and strategizing retention initiatives.

“It's really about just understanding what is available as a people practitioner, to report on to the business, that can really help to have an influence,” she says. “I think bringing the data driven insights is key for being able to influence good outcomes for the people in our organizations.”

Mindfulness as a new strategy for company cohesiveness

It isn’t all about tech insights for the tech HR leader, however. Bailey highly values looking inward as an important strategy for connecting with colleagues and improving the overall wellness of the organization.  

“I think mindfulness practices really help to create a supportive and resilient workplace and encourage our employees to navigate challenges with grace, and it's something that I'm a firm believer in,” she shares.

She even begins meetings with a short moment of mindful breathing, to ensure everyone on board is in the moment, she says, stressing that being focused on the task at hand is harder to achieve in today’s increasingly stressful environment.

She extends this philosophy to other HR leaders as well, acknowledging that connection can be hard to find, so finding a network of supportive people is a crucial career move.

“Sometimes being in a people practitioner role can feel a bit like being on an island, especially if you're the only person in your organization that's leading a people function, or if you have a small team,” she says.

“So I think it's really important to build a network, build a community, find your tribe outside of the company and of course, within, to find the champions in the business.”

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