FSQ Faces / Pamela Thomas, VP, Chief of Staff

Pamela Thomas Headshot

We welcome Pamela Thomas to the Foursquare team as Chief of Staff to Foursquare’s CEO & President, Gary Little.

Check out our Q&A with her to learn more.

Tell us about your career path and journey.

I’m originally from New York and I would say New York has been my best teacher – no offense, Dartmouth. Everyone thinks the city is going to love them and it loves no one, but it’s for everyone. It teaches you humility and grit and how to keep your ego in check. These are lessons that will take you farther than any formal degree. These lessons have helped me with my career – being able to hit the ground running, and get the job done no matter how large or small, while being humble and nimble.

My parents are originally from Guyana, which is geographically in South America but culturally it’s Caribbean. So in college, I was an English major with a focus on post-colonial literature. I would read all of the great Caribbean postcolonial authors like Walter Rodney, Derek Walcott, Jamaica Kincaid. Being an English major taught me how to analyze and how to communicate in an effective manner. I think one of the things that has made me such a successful salesperson is my ability to communicate and negotiate in a manner where people feel seen and heard. Regardless of the opportunity, listening is important. Even back then, the English studies were preparing me to be a successful salesperson because a lot of sales is about having good communication skills.

So how did this lead to you joining Foursquare?

I actually started my career in retail. I spent two years at Macy’s in their training program on the product development side and realized that I wanted to be a salesperson. You can develop a great product and think it’s a great product, but if the customer thinks differently then you have to shift, so that taught me the valuable lesson of being customer-obsessed or oriented. I’ve been in sales and customer success my entire career and was always in data content sales until I started the transition into tech sales at AWS where I most recently worked prior to joining Foursquare. I actually managed AWS’ relationship with Foursquare, so that’s how I got to know the team and a lot about the company. It’s nice to have that unique perspective and close connection coming into the company.

Did you always know you wanted to work in technology?

I’m an avid reader and it was a natural fit to go into content sales. I worked at Dow Jones for a number of years and then Dun & Bradstreet. A former SVP of Customer Success recruited me to AWS. One of the things that attracted me to the tech environment and ultimately led me to pivot into tech sales was that I really saw AWS taking chances and calculated risks on behalf of their customers that a lot of other companies weren’t.

Regardless of what industry you’re in these days, you have to be committed to moving fast and moving in a direction that resonates with your customer – and then taking the learnings along the way and transforming them into something meaningful. Working at a technology company has taught me that and I’m hoping to spread that kind of thinking and energy at Foursquare.

Tell me more about your role at Foursquare and what you’re most excited to do.

As Chief of Staff to Gary (Foursquare’s CEO & President), my role is pretty unique in that I’ll be working across several departments day-to-day. Therefore, I’ll have insight into what marketing is doing, what product is doing, what engineering is doing and so on. I guess you can think of me as Gary’s compass. My role is to really understand our teams and make sure that they are moving in the same direction so that we can continue to provide even more value to our customers and innovate and execute. So while the department functions might be different, the overall goal should be the same and we should all be holding each other accountable.

I’ll be working on a lot of challenges and pain points, trying to eliminate any roadblocks to communication and ensuring things are all moving forward. Growth is key – we want people to continue investing in our company and that starts with being aligned internally. There have been a lot of changes over the last few years but now the entire company needs to be looking ahead and working together as we improve our offerings and test and build new products. We have the right people here to do that and I’m excited to be part of the execution.

What do you see as the greatest challenges facing businesses today? What role can Foursquare play in addressing those challenges?

I think the greatest challenge that any business faces today is sustaining attention and relevancy. There are so many competing priorities and distractions plus we are living in truly unprecedented times. I try to think about myself as a consumer and what businesses or brands I tend to gravitate towards. They are usually the ones that have a well thought out identity, aren’t afraid to intentionally reinvent themselves if something isn’t working for their customers, and are unapologetic about what they represent because they have remained super close to their customers and built that trust. They understand their customers and know how to deliver a great product and experience. When I think about what we need to do at Foursquare, we need to maintain and continue to build on our customer-centric culture. Everyone should understand how their work provides value to our customers, whether directly or indirectly.

What’s the best advice you’ve ever received?

I’m a woman of color and oftentimes I’m in spaces where I am the only one. Earlier in my career, I suffered from imposter syndrome because of this. I would make unnecessary adjustments or feel the need to fit into certain circles or “clubs.” I think one of the best pieces of advice that I received is to stop trying to change who you are because your ability to be authentic is going to be one of the main contributors to your success. Your background is valuable and who you are is valuable. If you aren’t being valued, you need to change your environment because it is not the right one for you. Having a difference of perspectives and a diverse workforce is something that companies should want and something that should be celebrated.

When employees join Foursquare, they’re always asked to share a fun fact. What would yours be?

I like to wear a lot of vibrant, loud colors – that’s how I celebrate life. In particular, I wear a lot of Christopher John Rogers, GANNI and WRAY NYC. All bold designers who aren’t afraid to push boundaries.

Since you’re born and raised in New York, any local gem you could recommend?

So if you’re in Brooklyn, there’s an amazing Trinidadian spot called De Hot Pot. It’s small in size but giant in flavor. There’s no place to sit, but it’s just delicious and really close to Prospect Park. You can find me there most weekends when I’m in town grabbing a double, which is similar to a chickpea sandwich, then heading to the park to people watch. NYC is always a vibe!