Chili Piper operates in
Oyster hires
using Oyster

at a glance

Launched in 2016, Chili Piper is the leading inbound conversion software for high-growth B2B revenue teams. Their automated scheduling tools enable companies to qualify, route, and book prospects quickly and efficiently, ensuring a delightful experience for leads and customers. 

Chili Piper partnered with Oyster in order to scale their global team quickly and efficiently, while providing a fair and equitable employee experience. With Oyster, they doubled their headcount in less than a year, and now have 250 Pipers in 43 countries around the world.

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Key results
  • Chili Piper's team is 2x larger after less than a year hiring with Oyster
  • The People team gets to focus on more important stuff than manual processes
  • Chili Piper maintains a consistent “Piper” experience across 40+ countries

The challenge

As a company founded by immigrants, Chili Piper strongly believes in extending access to opportunity to talented people anywhere in the world. A fully remote and distributed company since day one, they wanted to build a culturally and geographically diverse team, no matter how much work it required.

True to their values, Chili Piper did build a global team—but it was a huge administrative and logistical burden to navigate international payroll, taxes, and compliance. If someone needed to change their bank information, or if there was an error in the payroll—everything had to be handled manually.

Tyler Parson, VP of People at Chili Piper, recalls what those days were like: 

“Before Oyster—we call it the Before Times—we were doing all of our international employee management manually. We were manually staying legally compliant and dealing with taxes in 40 different countries. It was a logistical nightmare. So when Oyster swooped in, it was a knight-in-shining-armor moment for us.”

These manual processes were also time-consuming, stressful, and risky. It meant having to deal with the constant anxiety of wondering if they were inadvertently making mistakes that might negatively impact a teammate in another country.

“We had to manually search for things in regards to legal compliance and tax laws. It was terribly time-consuming, inefficient, and potentially risky. Managing those logistics was very stressful.”

For Tyler, as a People leader, it’s the sort of thing that would keep her up at night: “Oh my gosh, if I mess this up, how is it going to affect this person in Iceland?” Operating in this way was clearly unsustainable.

Finally, as a U.S.-based company, Chili Piper found it hard to ensure the same employee experience for non-U.S. teammates. Pipers outside the U.S. often felt like they weren’t on an equal footing. If there was a problem, Tyler would have to tell them to “Slack this person or call that person” and just hope that the issue would get resolved. Chili Piper prides itself on being a people-centric company, so ensuring a fair and equal employee experience was a major challenge they needed to solve.

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Before Oyster—we call it the Before Times—we were doing all of our international employee management manually. We were manually staying legally compliant and dealing with taxes in 40 different countries. It was a logistical nightmare. So when Oyster swooped in, it was a knight-in-shining-armor moment for us.
Tyler Parson
VP of People at Chili Piper

The solution

Chili Piper eventually chose Oyster as their global employment partner in August 2021 because the two companies are aligned in their mission and vision—specifically the mission of expanding access to work to talented people worldwide, and the vision of a fully remote and distributed future of work.

Tyler also appreciates Oyster being a trustworthy partner with a human-centric approach to business, which comes across at every single touchpoint. She explains how a company’s ethos permeates everything it does:

“When organizations are human-first, like Oyster, it makes a difference in everything—the way the software is built, the experience of how it feels, the way in which they do business. At Chili Piper, we’re a fellow people-centric company, so when choosing Oyster, we felt like, ‘Oh, you're our people.’ There’s a level of trust there, and it was a really strong foundation for our continued working relationship.”

At the day-to-day operational level, Tyler appreciates the Oyster platform for its well-designed user interface that ensures a delightful experience for Team Members. After all, in a fully remote environment, the software tools that people interact with can make a big difference.

“The number one thing for me when talking about employee experience is the software they interact with. As a software company, we believe in beautiful tools and ease of use. All the other tools we saw didn’t have the user interface that Oyster does. When you’re an employee and you have to deal with payroll or benefits, it’s not inherently fun. So imagine if you can log on and have this amazing experience—it just makes the whole thing better.”

Oyster’s global employment platform isn’t just aesthetically pleasing—it’s also infused with country-specific legal knowledge and expertise to ensure that compliance is built into the platform. The guidance provided by the platform is further supplemented by legal experts on the Oyster team.

The results

As a fully remote company, doubling or tripling in terms of headcount is “incredibly challenging,” says Tyler. All the more so if you want to “make sure that as the company scales, the employee experience stays really intimate and personal and positive,” she adds. Thanks to Oyster, Chili Piper was able to scale rapidly while also ensuring a consistent employee experience across 40+ countries.

“The biggest value has been the employee experience. You can go online and see everything you need within this one platform where everything is centralized. It brings a level of autonomy that our non-U.S. employees didn’t have before. It truly creates an equal experience for everyone. Oyster has allowed us to provide the best experience for our employees, no matter where they live in the entire world.”

For the Chili Piper team, it’s a huge relief to not have to figure out compliance in 40 different countries on their own. Using Oyster has been a huge time-saver, but equally important is the peace of mind from knowing that their global workforce is in good hands. Whenever they need support, the Oyster team is a helpful and knowledgeable partner.

“With Oyster, we’re saving so much time. Otherwise, we’d be spending literally twice as much manual time, which was already unsustainable when we were 100 people. Now that we’re 250—it’s unthinkable. From a leader perspective, I can sleep easy at night knowing that we’re not breaking some law that I didn’t even know existed. If we have questions, we can just Slack our Oyster team, and they’ve never been anything but gracious and happy to help.”

As a fast-growing startup, Chili Piper has been able to scale quickly thanks to the efficiency, speed, and compliance that Oyster has made possible.

“The biggest impact that Oyster has had on our team is certainly efficiency and speed. We’re able to onboard employees a lot faster and with a lot less anxiety about whether we’re doing it right. With Oyster, we trust that we did do it right. And if there’s ever any problem, we just ping them and they fix it for us. They’re a genuinely collaborative partner.”

With the administrative and logistical burden of hiring globally taken care of by Oyster, the People team at Chili Piper has been able to focus their time and attention on other things, such as ensuring an excellent experience for their global team.

“Oyster has taken away the very important logistical work that must be done—and must be done correctly. It’s taken that stress off our plates. They manage all of it with a smile, and it has allowed our team to spend our time and energy reinvesting in things that are going to continue to add to the employee experience.”

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Oyster builds trust by genuinely being experts in their space. The platform was built using experts across the world to make it above board and safe and trustworthy.
Tyler Parson
VP of People at Chili Piper

The future with Oyster

Tyler is excited about continuing to strengthen the employee experience that makes Chili Piper unique. After “being in growth mode for so long,” she says, it’s now time to invest more fully in the “amazing global team” they’ve built by providing more robust benefits and perks. 

Meanwhile, the way they use Oyster has evolved as they’ve grown. Oyster has now become part of their internal systems around which they can build robust and sustainable People processes to support the company in the long term.

“Now that we’re at 250 employees, we’re actually building processes and systems internally around Oyster. As we scale with Oyster in our tool belt, we’re building things to make sure that as we scale, we can still use Oyster to its full power and ability.”

Having experienced firsthand the tremendous benefits of having a globally distributed team, Tyler believes strongly that companies that haven’t made the leap yet are missing out.

“There’s going to be times when it feels overwhelming or challenging, but that’s why Oyster exists—to help. Embrace the challenge because globally diverse teams literally do better work. The more ideas you have in the room, the more perspectives you have at the table, the better the outcomes for your business and your customers.”

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