Toast Careers

Samantha started at Toast right after graduating. Hear more about her experience and her advice to other new grads:

What led you to pursue a career at Toast? How did you hear about the opportunity?

Growing up in Massachusetts, I have always been interested in building a career in Boston. As graduation approached, a family friend of mine connected me with a Sales Development Rep (SDR) at Toast who is now a top-performing Account Executive (AE). Shoutout to Maddie Strahle! Throughout the entire interview process, I was consistently impressed by the warmth, professionalism, and genuine support of everyone I spoke with. It was clear that Toast's culture is rooted in both excellence and collaboration, and it reinforced my excitement about the opportunity to be part of such a remarkable team in my favorite city.

What led you to wanting to be in a sales role?

As a college lacrosse player, I developed a competitive drive that fuels my desire to excel and meet my goals. I initially found the idea of working in sales intimidating but after speaking with current and former SDRs, I realized that there is a feeling of motivation and satisfaction in striving to exceed expectations and hit challenging goals. This perspective made me excited about the potential to thrive in a sales role.

As a Sales Development Rep (SDR), what were your focus areas and what skills do you feel you need to be successful in an SDR role?

My role as an SDR has built the foundation for my success at Toast. From the beginning, I focused on building strong relationships with AEs, as I believe close collaboration is key to achieving results. These relationships helped me refine my talk tracks and understand how I could improve outreach strategies. As I mentioned earlier, my competitive nature drives me to exceed expectations, and developing this mindset through relationships with AEs has pushed me to break records along the way. My success as an SDR wouldn’t have been possible without embracing rejection as an opportunity to learn and improve. These are just a few of the skills that helped me excel during my tenure as an SDR and continue to drive my success throughout my time at Toast. 

You were recently promoted to an Enterprise BDR role, what skills are you looking to invest more in with this shift to a new role?

I’m incredibly excited about the opportunity to help build the Sports and Entertainment vertical as a BDR. While creating a pipeline from the ground up and earning trust within the industry is no easy feat, I firmly believe that nothing worthwhile comes without challenge. 

As I approach my one-year mark as an Enterprise BDR, I’ve developed a variety of skills that have been instrumental in my growth. I’ve refined my outreach methods, deepened my understanding of the Sports and Entertainment sector, and built the confidence to position Toast as a key competitor in this vertical.

That said, there are still areas I’m eager to improve. For instance, I want to master running discovery calls with prospects, using my product and industry knowledge to spark interest. Additionally, I’m keen to spend more time seeing the sales cycle through to completion, enhancing my cold-calling approach and preparing me for future career growth.

What advice do you have for other early career individuals looking for their first opportunity?

My advice would be to explore a wide range of opportunities. During my job search, I applied to several companies and positions, taking full advantage of my Business Administration degree and minor in Mathematics and Analytics. This broad academic background opened up a wealth of potential career paths for me. 

Equally important is reaching out to current employees at companies you’re interested in. I’ve found that speaking directly with people in the field provides invaluable insight into the company culture and role expectations. Personally, I’m always happy to connect with early career individuals and share my experiences at Toast, as well as offer guidance on starting a career in Sales!

What Toast value resonates with you the most and why?

The Toast value that resonates most with me is, "We're hungry to build and learn." This principle has been central to my journey here for several reasons. First, Toast was my first job after graduating college. I was eager to prove myself, but I also recognized how much I still had to learn. In those early months, I focused on absorbing everything I could. I made it a priority to listen and learn from seasoned SDRs, managers, and AEs, knowing that growth came from staying curious and open. 

When I was promoted to Sports and Entertainment BDR, this Toast value took on even greater significance.  Joining a brand new team tasked with building the Sports and Entertainment division from scratch required a growth mindset and hunger to build and learn.

The motivation to create a successful team has been a powerful force. While there were certainly stressful moments and unavoidable mistakes along the way, each challenge has served as a valuable learning experience. I’m excited to continue contributing to the growth of the Sports and Entertainment team. We’ve definitely found our rhythm, and I’m confident we’re on track for an incredible 2025!