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The Future of Work and Benefits: Interview with Gillian O'Brien

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July 21, 2020
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We are excited to present you with another great individual behind the company that supports the future of work!

We met Gillian, the co-founder and CEO of Cherry at Y Combinator W19 last year. With her sister Emily, Gillian is building a platform that is reimagining perks for employees. Their energy and passion to improve the future of work immediately sparked interest. While we are exploring ways to collaborate, we asked Gillian some questions to see what she thinks the future of business holds.

What inspired you to build Cherry?

The company I worked for prior to starting Cherry was very perk-heavy, specifically in the food department. Sadly, I have deadly food allergies so I never really got to “engage” in these perks. I wished I could instead get the money back from the company to use towards something else that would make my life easier. I was a typical millennial in the workforce; trying hard to balance my health, relationships, family, and career. I wanted my company to help me save money on my commute or my gym membership.

My co-founder is my sister. We knew we wanted to work together for a long time - so when I shared my challenges with her, we got super excited about building a solution. Inclusion is a priority, yet a very real problem for most companies when it comes to culture, perks, and benefits. We’re building Cherry because we want to change this. The workforce is more diverse than ever, and people have very individualized needs. Cherry is a clear solution for the modern company.

What do you think will be the next generation of work & the next generation of benefits?

The future of work is more diverse than ever before, and next-gen benefits will evolve to fit the demands and expectations of those workers. We're moving towards a workforce that is more well balanced in terms of age, gender, and race. We're also looking at a workforce of full-time and freelance workers, four generations, and no restriction in terms of an employee's geographical location. Standard healthcare and a 401K won't cut it anymore. With all of these individuals in mind, a company should be prepared to offer childcare, fertility benefits, student loan repayment, mental health support, pet insurance, fitness memberships, transportation options, and personal/professional development programs. This is no small task, so platforms like Cherry that put benefits selection in the hands of the employee will become the norm.

What are some of the most interesting perks companies offer and what do people enjoy most?

We've seen companies offer very unique perks. We even created a perk generator of the 100+ company benefits we'd learned about while working on Cherry! On-site haircuts, flowers on each desk, and in-office chefs are definitely attention-grabbing (though maybe not so enjoyable for the remote employees!) But in terms of what people like the most, it's the choice. In fact, Metlife recently reported that the "ability to customize benefits to fit one's needs" ranked higher than "ability to work from home" when employees considered what would make them the most loyal to a company.

How can you offer perks to contractors/freelancers who are not employees?

Reach out to us, and we'll get your employees set up with Cherry! : )

What benefits can companies offer to their remote employees?

With Cherry, you can offer all kinds of benefits. Gym memberships, Uber and Lyft, access to workspaces (WeWork, Deskpass), Headspace, Spotify, free lunch, education and professional development courses, the list goes on and on.


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Cherry lets employees choose their own workplace perks. With Cherry, employers cover their employees' favorite consumer services (ex: Netflix, Spotify, ClassPass, Lyft), instead of wasting money on perks no one uses like in-office yoga and ping pong tables.

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