Chief Chat: Casey Bailey

Deel’s head of people details the inner workings of a remote-first company.
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· 4 min read

Casey Bailey remembers the time before remote work. As a former head of global HR business partnerships at Uber, remote work used to be a rarity. “There was no way Travis [Kalanick] was going to have engineers not sitting in engineering hubs working together,” Bailey told HR Brew. But then, as you might recall, the pandemic shook things up a bit.

Building a remote workforce can present a maze of hurdles related to regulations and compliance—Bailey knows this firsthand as HR tech company Deel’s head of people, where she’s led the company’s efforts to rapidly scale over the last two years, building out a global team, often using its own product to handle payroll and compliance. Bailey talked to HR Brew about the company’s recent trajectory, in addition to how to keep the company’s almost 2,600-strong remote workforce engaged, and the importance of centralizing an HR tech stack.

How do you keep your remote workforce engaged? How do you calibrate engagement?

We recently ran our first engagement survey last November. We went from 50 to 550 people in 2021, and [then] 550 to 1,900 in 2022, and now we;re closing in on 2,600. We sit in almost 100 countries around the world.

We thought it would be pretty interesting to see the differences in who was hiring…[was it] managers, leaders, [or] talent acquisition, getting involved in that evolution? From a value standpoint, how are people feeling about working at Deel every day and the work that they do? It’s pretty interesting, because [according to the survey] 94% of people feel proud to work at Deel. But more than that, [were] the comments people left about the work, how closely they feel aligned to the mission of what we’re doing because they’re able to sit remotely in these various countries around the world, and also they’re able to connect [clients] to the same type of employment opportunities for really cool companies around the world.

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What’s your approach to keeping younger, entry-level employees engaged?

We’ve really heightened our focus on [this] over the course of the last nine months. We have an internal culture and comms manager that actually sits on my team that works cross-functionally with our growth and communications teams, managers, [and] talent acquisition to think about how we prepare [younger employees].

We have had people opt-out before [a job offer] saying, “I thought about it, and I need to be hybrid, or I need some more connections with people.” That tells us we’re doing at least an OK job of really expressing to people what it’s like to have self-discipline management. Sitting remote, you have to take an active part in connecting. We try to communicate that and when folks are onboarding, we go above and beyond in trying to connect them with our tools.

We’re a heavily Slack-based company, and we have very high participation in our Slack groups, for instance.

How important is it to centralize the tech stack, and what are the benefits it can bring to your department?

It’s my dream. If you think about hacking your tech stack together, and if you’re operating in a global work environment, and specifically with various worker types from contractors to direct employees across multiple countries, that level of complexity grows and grows. One of the barriers to entry is simply the knowledge base, the know-how to be able to [scale a remote workforce]. We’re striving to do that by building our HRIS product for companies like ourselves, and sharing our knowledge.

If you can productize that knowledge…literally anyone at your company that’s responsible for hiring that’s responsible for hiring could sit down, choose the worker type and country, and we’re flowing you through exactly how to do that in an easy and simple way. So, it’s breaking down that barrier of being able to hire anyone anywhere to meet your headcount goals.

HR is challenging. HR news doesn’t have to be.

HR Brew keeps you effective in the fast-changing business environment.