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Growing too fast kills most startups but Upside is flying high

people shooting nerf guns at taco champion
The most recognized Upsider gets the coveted taco trophy but must protect it from taco bandits!

If you ask business owners what the hardest thing is about starting up, you’ll inevitably hear about how difficult it is to create a lasting work culture. For many start-ups, those first hires can make or break your culture.

Now imagine how hard it is to create a lasting culture when you hire over 100 people in your first year of business.

This is a reality for Upside, a travel booking site just for business travelers and a HeyTaco customer, who promises to make every business trip better–from start to finish.

What’s impressive is somehow they’ve managed to hire at a breakneck pace and build an enviable work culture. They’re highly rated on and one of our most appreciative teams using HeyTaco.

We recently chatted with their Chief People Officer, Cristyn Girolami, to get an inside look at what’s driving their success.

Hire for cultural fit

Before Upside made a single hire, the founding team put a lot of thought into the type of work culture they wanted to create. The result was these 3 core values to guide the evolution of their culture:

  1. Delight: We delight customers. We delight each other.
  2. Crank: We work hard. We work smart.
  3. Jive: We make an active effort to work well with one another.


When they evaluate job candidates, cultural fit is a required consideration, even if you are the next Albert Einstein. Upside believes this culture first mindset is a critical factor to their early success.

Hiring people is one thing, working together is another challenge entirely. As you add more people to your organization it becomes increasingly complex culturally and strategically. To survive this complexity Upside relies on empowering its people and effective leadership.

The power of leadership and empowerment

When it comes to working and growing at Upside, their company president Scott Case, is a proponent of Servant Leadership and lives the people side of the business. This creates a large focus on empowering people to take control of their own development.

People at Upside check-in with their manager at least once a week to talk about how they’re doing and any opportunities for improvement.


An Upsider celebrates winning the taco trophy for the month.

There are also quarterly check-ins with someone from the People Ops Team and/or coffee or lunch with the President. These check-ins aren’t tracked, but team members are accountable for making them happen.

Overall, the goal is to empower team members to guide their own professional growth with regular conversations.

But what is it that really makes this company tick?

From our chats with Cristyn and other Upsiders, we knew something bigger was at play.

The voices around us

After digging in, it became clear this company has really figured out how to communicate across the organization in a transparent way.

This open dialogue helps to surface any issues, and then the company can figure out how to solve them as a team. When you’re growing as fast as Upside, there’s always going to be pains. The good news for them is they’re easy to spot and they can work together to fix them.

This makes everyone an active participant in shaping the company’s culture, and that must feel pretty great.

What we’re taking

When hiring at HeyTaco I know we’ll take at least 3 things we’ve learned from Upside:

  1. Put a lot of effort into figuring out what type of work environment we’d like to create and hire for cultural fit.
  2. Development is a two-way street: hold leaders and team members accountable for checking in with each other.
  3. Empower every team member to shape our culture with transparency and 2-way communication.

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