Paige M.

Senior Program Manager, Employer Brand

Two years ago, Megan Anderson joined the Toast team and ever since, she’s been revolutionizing the way we empower the restaurant community. As our Chief Customer Officer, Megan is hyper-focused on the customer experience. Her team represents the voice of our customers and ensures we’re setting restaurants up to thrive. Learn more about Megan’s career path, goals for the year ahead, and advice for growing your career!

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Can you tell me about your career path and how you ended up at Toast?

I started my career in consulting and then returned to the space after attending business school. While I enjoyed this time, I reached a point where I wanted a more hands-on role. When my husband was offered a new position that took us to Europe, it was the perfect time for me to make a career change. 

I was incredibly fortunate to join the Booking.com team, launching their vacation rentals business, which is the biggest competitor to AirBnB globally. I affectionately refer to Booking.com as having been at the multi-billion dollar start-up phase (much like Toast today). There was a real product-market fit and they were no longer at the start-up stage, but there was still an incredible opportunity to scale and drive impact. 

After some restructuring at the organization, the CEO offered me an unexpected opportunity: I was asked to lead the Customer Service team. Leading vacation rentals, I worked with every department in the business, except customer service. Although I didn’t know much about the space, I was excited to learn. My years working as a consultant gave me the skills needed to tackle a new industry at a new company where I had no prior experience, and to add value quickly. The cross-functional nature of my time at Booking.com thus far prepared me to work across departments on the key customer experience and scaling challenges in front of me. In the end, I was able to grow so much professionally and personally in this role. The global scale and impact of my team was incredible, and it’s an experience that equipped me for the opportunity and challenge in front of me at Toast. 

When my husband and I first moved to Europe with our then-18-month-old, we figured we’d stay for two or three years. Five years later, I was pregnant with my fourth child, and we realized it was time to move back to the United States. I’m originally from California, but my husband was born in Massachusetts, so we decided to move to the east coast. Once we got settled here, I wanted to try something completely different and ended up in private equity. I quickly realized this wasn’t the right match for me, but COVID-19 hit. Between the uncertainty and juggling home schooling with the kids, it didn’t feel like the right time to start a new career search.

Megan and her family on a recent trip to Italy

When I did decide it was the right time to make a move, there were a couple of things that were very important to me in a new role. I needed to find the right leaders and the right culture of an organization– neither of which are easy to find through a LinkedIn search! I was open to different roles and different industries, but it was critical to me that I enjoyed where I was working and who I was working with.

Ironically, on the same day, I had two completely separate introductions to leaders at Toast. I spoke with both of them, which led to me speaking to more members of the team. Between the culture, the leadership team, and the opportunity, Toast just felt like the right fit. I was thrilled to be in customer service where I had so much domain experience, and our restaurant customers have so much in common with the independent hotels I had been working with. It is great to be back in the customer service and hospitality spaces. The rest is history!

You mentioned a previous CEO who helped you determine your next step. How do you help your team grow their careers? 

I’ve been so fortunate to have mentors and bosses that have opened up new opportunities for me. Now, as a leader, I’m always looking for ways to help my team grow and demonstrate what they’re able to do. I encourage them to take on new challenges, even if they don’t have experience in the spaces yet, because those were the moments that helped me develop in my career. 

I once had a previous boss ask me: “What do you want to do next?” I was relatively new to the role and things were going well, so it wasn’t a career transition conversation, but rather him pushing me to think about how I wanted to grow. This conversation put my goals on his radar so that he could help me move in the right direction. I think more importantly, though, it put the agency on me to define my own career goals. I shared what matters to me in terms of the type of work I want to do, how I want to spend my time, and what excites me.

When I joined Toast, asking this question helped me get to know my team. Having dedicated time to discuss goals turns the focus on career development from just a natural progression to a more intentional discussion, which sets us all up for success.

Megan hosting a leadership coffee chat at our new Boston headquarters

I’d love to learn more about how you work with customers. What keeps you connected to the customer experience?

In my role, I work in a lot of different areas, which is exciting, but can be overwhelming at times. For me, a big piece of staying motivated is finding a connection to people. Whether that’s connecting back to our customers, with my direct reports, or to the broader Customer Success team, being connected to people is inspiring for me. I want to know where they’re coming from and what’s going on in their lives. It’s important for building working relationships, strengthening trust, and working well together. I encourage all Toasters to think about their work through this lens.

To understand the customer experience, you need to ask questions and listen. I realize that sounds simplistic, but when you’re working with customers, data alone can’t show you the whole picture. We’re working with real people and real emotions. Our customers have a lot of passion and love for what they do, so by asking open-ended questions and really listening to their responses, we can solve issues and gain a deeper understanding of how we can best serve them going forward. 

Megan cutting the ribbon at the opening of our new office in Omaha, Nebraska

What is one goal you’re working towards in 2024?

We recently refreshed the Toast values, and one is “we’re all in customer success.” I’m excited to help Toasters bring this value to life. 

One of the amazing things about our customer base is that employees can easily interact with customers any time they’re at a restaurant. Employees are very passionate about supporting the restaurant community and I want to see how we can channel that energy to deliver an even better experience for our customers. We want all employees– regardless of their role–  to have the tools and resources they need to truly understand how our products work and feel connected to customers. 

When I first joined Toast, I immediately noticed that everyone wants to do right by our customers, even if they aren’t in a customer success role. We’re all customer-obsessed, but oftentimes our teams often work in silos. I want to flip this narrative. Instead of thinking about a problem from your team’s perspective, I want to focus on how the customer is experiencing things. When we take a step back and collaborate more closely internally, we’ll deliver even better services for our customers. As an added benefit, I think working more cohesively will also enhance the employee experience internally.  

What are some of the skills that make someone successful on your team?

I think this comes back to me moving into customer service with no formal experience in the space. I was not brought in because of technical expertise, but rather my eagerness to learn and make an impact. Things like work ethic, motivation, and ability to work with others are all far more important to me than knowing someone has done this specific type of work before. Attitude over experience any day!