Employee Perks Are Stiff And Boring. Cherry Makes Your Work-Life Flexible And Exciting Again.

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I got the chance to speak again with Gillian O’Brien, co-founder and CEO of Cherry. Cherry is an office benefits startup that allows employees of companies to choose their own perks. Our conversation focused on the problem she's tackling in the workforce benefits space at Cherry. O’Brien obtained her Bachelor’s degree from New York University. After graduating, she and her sister participated in Y Combinator’s startup accelerator as part of the Winter 2019 (W19) batch.

Check out my past conversation with her here: Cherry's Gillian O'Brien's Life As A Founder, Sister, and Yoga Instructor.

Frederick Daso: Why do companies need more flexible perks and benefits? What are the underlying drivers of employee demand for flexibility in the benefits they receive?

Gillian O'Brien: Employee expectations have changed: they expect flexible working conditions, better awareness of mental health issues, inclusive environments, purposeful work, and excellent benefits. Compensation isn't the sole motivation for staying with a company anymore.

The unemployment rate is the lowest it's been since 1969. Today's workforce has more options than ever before. They don't need to take on traditional 9-5 jobs - they can just as quickly join the 1099 economy. Attractive benefits make a huge impact and help companies stand out from competitors.

A thoughtful perk program improves culture, engagement, and retention. Perks are also an opportunity to help your employees be more productive at work. When they know their commute is covered, their babysitter for the weekend is booked, or that they don't need to figure out lunch because their company has it covered… it's one less thing on their mind. They can focus on the moment and bring their best self to work every day. Knowing their employer cares about them has an impact on their job satisfaction and loyalty.

Daso: What's driving the growth in this particular market surrounding flexible perks? Do more perk providers want to provide on-demand access to their products and services? Do the employees' companies want to decrease the cost of delivering these perks?

O'Brien: The trends outlined above contribute to the growth in the market: diverse & dispersed workforce, changing employee expectations, blurring of work/life, etc.

Employers know this is an issue and try to solve it with broken systems like stipends, reimbursements, or multiple direct relationships with vendors. These are bandaid solutions that ultimately fail. They're manual processes with low engagement rates, no insights/reports, error-prone, unscalable. 

The demand for Cherry comes from HR and Finance leaders that need to scale flexible programs cost-effectively. They need software to do that.

Daso: How did you come up with the idea of the Cherry Card?

O'Brien: It was essential to find a way to give employees the ability to self-manage their account and choose their perks. The best way to do this was by empowering everyone with their corporate card. Part of the pain with old systems was around needing constant approval. With Cherry, the virtual cards are programmed to work only at vendors that have been pre-approved by employers. Also, an employee can use only up to the allowance amount set by the company. 

Daso: Why are you and your co-founder, Emily O'Brien, the ones to solve the core problems in the employee benefits space?

O'Brien: We experienced the problem ourselves, and now we're doing something about it. We didn't need a background in HR to identify a need and come up with a solution. Instead, we had a vision, we brought it to life, and it's working.

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