January 27, 2022

Cristina Ciaravalli on creating a path for the next generation of fintech sales professionals

Madeline Perretta

What is your role?
I am a Mid-Market Account Executive on Plaid’s Revenue Team.

Describe what you do in a few sentences.
My day-to-day is focused on helping midsize companies get up and running with Plaid. I really enjoy my job because I get the opportunity to guide our customers through their unique Plaid journey. As their main point of contact, I lead early conversations to determine how we can best help their business grow - this includes inception all the way to their launch with Plaid and beyond!

How does your work impact people's financial lives?
I work with companies that are shaping the future of financial services and this is what makes my role so exciting. Many of my customers are creating new apps and services to help make finances more accessible and inclusive, such as helping people budget, save for retirement, and manage their debt. There are so many incredible ideas out there and it is a privilege to be on the team at Plaid that helps turn our customers’ ideas into a reality.

Tell us about the culture of inclusion at Plaid.
I vividly remember walking through the Plaid HQ doors in San Francisco in 2019 and feeling a sense of belonging. Every single person I met was inclusive, helpful, and eager to get to know me. I received dozens of emails from my new co-workers, including William, our Co-Founder, expressing their excitement and welcoming me to the Plaid family. I felt incredibly grateful to be part of a company that truly energizes its employees.

This culture of inclusion still rings true today. Over the last couple of years, we've done a lot more to build out a robust Diversity, Equity, Inclusion, and Belonging program, which I have had the opportunity to help grow. We also have our own version of Employee Resource Groups - called Plaid Community Groups - which include groups like Plaids of Color and Women+. Our PCG’s have empowered employees to make connections, discuss DEIB challenges, and build company-wide initiatives. These conversations have enhanced our work environment in a positive way. I am personally a member of Women+ and it has been an absolute joy to be a part of the group. The Women+ team organizes sessions called “mini meets” where we are randomly placed in a group of 4-5 participants from different teams who will regularly meet 4-5 times over 3 months to discuss personal and professional related topics. I always look forward to these meetings and feel that they have helped me cultivate strong relationships with my colleagues, even in a remote world. 

What do you love most about working at Plaid?
I have two answers. The people and the pace of innovation. The people are the heart and soul of this company and are the reason why I feel motivated to do my best work each day.  I really do love the people and the spirit of the company. There is an energy about Plaid that is contagious and I felt it on my very first day. Prior to Plaid, I worked at larger financial institutions where it took a significant amount of time to enact change. At Plaid, we move fast and are a nimble company. For example, in 2020, at the start of Covid, Plaid built a free PPP lending product essentially over a weekend. To see Plaids across multiple teams come together to create something truly impactful, and so quickly, was beyond inspiring. It made me feel proud to be part of something so much bigger than myself. 

Let’s rewind to before Plaid

Growing up, what were your passions or interests?
Okay. So, this is embarrassing, but I got in trouble with my principal for making string friendship bracelets and selling them on the playground for two dollars. I suppose this can be considered my first job…what can I say, I live for the side hustle...ha. But, the moral of the story is that I have always had this inherent drive to do more, create more, be more. I played a bunch of sports growing up so I have a slight competitive edge which has lent itself nicely to my career in sales. Additionally, I love building meaningful connections with people and this is a trait that stems from my youth.

Describe your journey into sales, what did your path look like?
I went to school in North Carolina and I didn’t really know that tech sales was a career option. I went through an undergraduate business degree program, where the standard career path was to work in consulting or at a big bank.

After graduating, I got a job at Goldman Sachs in sales and trading. Although I found trading to be very interesting because of the technical depth, I felt most excited by managing the relationship between the internal traders and the external clients. Working through dissonance with traders and clients can be challenging because both sides are set on winning. However, during these meetings, something sparked inside of me. I realized that I loved helping people navigate through tough conversations to find a solution. After working in trading a little bit longer, I knew that I wanted my next role to be grounded in impactful work and helping people problem solve. Plaid could not have been a better fit. 

You have been at Plaid for a few years now, how has the company changed? What have you learned?
The company has changed a lot. When I joined, it felt like I was truly on a rocketship. Each week there was an exciting announcement, some new product capability was built, or a new region we were entering. It was incredible to see the growth that came after our Series C, acquisition of Quovo, and launch into the UK and Europe. Our explosive growth means we have brought on many new team members and this has made the company feel bigger. Since I joined we have grown from around 200 employees to over 1,000 today! We now have more formal processes, more resources, and overall more organized chaos. Despite the change, at our core, we are still the same scrappy fintech company with the same values and mission. That has not wavered. 

I’ve learned that when you go into a startup or any company that's this high-growth, it's not going to look the same in the next month, quarter, or year.  It is important to acknowledge that the only constant in a start-up is change, so you need to feel comfortable working in ambiguity.  The second thing is to trust management and trust your leaders. Your leaders care and have your best interests in mind, so if you feel the need to understand something on a deeper level lean on them for support. Remember that they will have more context on company decisions or initiatives. 

Lastly, is getting behind a mission you believe in. There has been change at Plaid and that will only continue. If you look in the nearer term, as with any company, there are still inevitable challenges and things we need to figure out, but I'm so bullish on Plaid and confident about Plaid's future. I'm excited to be a part of building a more equitable financial future and to look back to see all the work that we have accomplished since I’ve been here fuels me for what’s to come. 

How have you helped the sales function grow at Plaid?
As I mentioned earlier, there is little visibility into what Silicon Valley consists of in North Carolina. Not one person in my entire four years at Wake Forest ever said, “Go be in tech sales” or “You should go work for a start-up”. I wasn’t even familiar with these terms!

One day, as I was preparing to make the jump from Analyst to Associate on Wall Street, a Plaid recruiter reached out to me. I took the call and went through the interview process with excitement, but also apprehension. I earned an offer to join the team in 2017, but didn’t feel ready to make the jump into tech at the time. It actually took me four years of working in traditional financial services before I knew it was time to pivot into tech sales and a company like Plaid. This would have been an incredible first job out of college and probably saved me time as I was trying to figure out how to shift my career while trading bonds!  I now feel this need to pave the way for the next generation of tech sales professionals earlier in their careers. 

Since joining Plaid, I have helped organize on-campus recruiting events at Wake Forest to speak to Plaid’s mission and impact with the intention of attracting new talent and getting students excited about sales. From our events, we have received upwards of 100 resumes and even hired our first ever sales interns, who now happen to be full-time employees. We have eight Demon Deacons on our team and counting. I feel that I am on a mission to help make the transition from college to a career a little bit easier for folks who didn’t grow up around fintech.

Are you also involved in the broader fintech community?
I sure am! I am part of the This Week in Fintech newsletter team. Interestingly enough this newsletter was prescribed to me as a “must read” on my first day at Plaid, and years later I am now part of the team! Nik, the lead writer, began getting readers together for community events in 2021. I showed up to one of his networking events and met him and we had a great conversation about all things fintech. Shortly thereafter, I came aboard the team to help co-lead community strategy. We now plan 50+ Fintech events per year in cities from New York to LA and Lagos to Berlin. It’s been an incredible opportunity to grow my fintech network, learn more about the industry, and meet cool people!

We hear you love to cook, can you tell us more!
I owe this all to my mom and grandma, they’re both excellent cooks. Growing up I always admired their culinary prowess. However, it wasn’t until college when I studied abroad in Florence that I really began cooking for myself. I would walk around Italy with my best friend and go to the local markets to pick up ingredients to cook whatever dish we were craving. I remember picking the figs off the trees at my school's campus and then going home to grill them and make a fig and goat cheese pizza for a casual Monday night dinner. It has become a form of expression for me. I do have my own food blog and hope to make a cookbook this year! 

What is your single greatest passion?
This is absolutely the easiest question to answer. Hands-down, people. I just genuinely love people. I love meeting new people, learning their stories, and what makes someone tick. This is why I feel a special connection to sales and recruiting new people to Plaid or fintech sales. Each conversation I have in my role is a chance to learn something new about someone and to help them solve a problem.

What is the best piece of advice you have received?
A piece of advice that has impacted me was given by a Plaid leader. When I first joined Plaid, my sights were focused on how I could move up into the next role…I already told you I have a competitive edge…ha. In the process of asking how I could get promoted or move up, I was told that “having a focus solely on the target would inhibit me from building the foundation I needed to succeed in hitting the mark”.  This caused me to pause and to reflect on the fact that in order to do well in my role and to work my way up to the next position, I needed to be successful in my day-to-day life. I approached each of my calls, emails, and meetings with determination and a clear focus to accomplish the work directly in front of me. Over the last couple of years, I have experienced different promotions in my role and credit is due to the shift in my perspective that a strong foundation is a key to success.