Boxer Spotlight: Caroline Caselli, Small & Medium Business Manager


At Box, we believe great ideas can come from anywhere in the company. We are committed to building a culture that supports personal and professional growth. In this new series, we are excited to spotlight Boxers across the entire organization, at various stages in their careers, to showcase what #LifeatBox is all about. With that, we’re excited to introduce you to Caroline Caselli, a Small & Medium Business (SMB) Manager based in New York City. 

What made you choose Box and how long have you been at the company? 

I joined Box in October 2013, so I'm quickly approaching my 7 year mark! In hindsight, I had absolutely no idea what I wanted to do, but I was wrapping up a post-graduate job leading the Sales & Advertising department of my college newspaper and also living in the heart of Silicon Valley, so I was loosely looking at tech sales roles. I knew a couple of people who worked at Box who raved about the culture. I quickly became obsessed with the product, people, and company through the interview process and here we are, almost seven years and six roles later. 

What was your role when you first started at Box and what is your current role today?

I started at Box as a Sales Development Representative (SDR), which is Box's entry level sales role. The SDR role primarily answers inbound outreach to Box and responds to online contact forms. This was a really fantastic first role at Box because you're exposed to so much, so quickly. I worked my way through our Inside Sales organization and then up into our Field Sales team as an Account Executive. Soon after, I was hungry for a new set of skills and experiences. I moved into my current role as a Small & Medium Business (SMB) Manager at the start of the fiscal year in February 2020. This is my first year as a Manager, so I've just eclipsed the 6-month mark and manage a team of seven AE's covering the Northeast and Mid-Atlantic.

How would you describe the transition from being an individual contributor to a people manager? What were some challenges? What were some great learning experiences?

The transition has been wild, overwhelming, exciting, growth-filled, empowering – many adjectives! 

I had a lot of uncertainty about going into management –Was it the right time? Would I like it? Would I be good at it? – and candidly, I struggled with that career decision for several months. However, almost immediately after starting the role, I realized how right and aligned it felt. I love developing people and teams and I enjoy the aspect of my role where I'm able to improve internal processes. As Box grows, new teams spring up, which leads to more opportunities. My career excelled because I had the opportunity to move to NYC with Box and help build out the NYC Sales team. I felt ready to learn and try something new and Box has been a safe space to explore that. I also feel strongly about developing people and having a seat at the table with sales leadership to drive conversations around diversity, inclusion and belonging in sales. I'm so grateful that I decided to make the transition to management.

When it comes to challenges, 2020 has been an overwhelming year for everyone, including new managers! About one month into the new role, New York and our NYC office shut down. All of Box shifted to work-from-home and there was a lot of very justifiable fear and uncertainty about what this meant for our lives, our health, our families, and our jobs. I had some members of my team whose families were personally impacted by COVID, teammates who had to uproot their lives and others brand new to the role who weren't getting the typical on-the-job exposure and training that we took for granted in the office. We also had teammates who were alone – everyone was impacted deeply in some way. As a manager, I think it forced me to quickly jump into deep empathy and problem-solving mode. I approached the situation with empathy first to make space for my team members to take time, vent, grieve and be humans. My secondary approach was to jump into rapid problem-solving because absolutely no one, anywhere, knew what to do. My philosophy was to continue to try new things, capture outcomes, and share anything that was working well across the team and segment. The team ended up having a great quarter and exceeding our pipeline target,which was a huge success given the adversity we faced.

How do you go about developing individuals on teams?

At the individual level, I try to understand what their personal motivations and goals are, what their unique strengths are, where they want to go next, and then motivate and coach accordingly. Everyone on my team either wants to go up market as an Account Executive (AE) or into management, both of which I've done here, so I'm able to draw on my own experiences, best practices and pitfalls to listen and provide feedback in a way that's credible to them. I also think team camaraderie is important and I've personally grown a ton by being on close knit and high performing teams at Box. At the team level, I try to foster a culture of best practice sharing and identify opportunities to up-level the team based on broad trends, whether that's bringing in successful Box sellers from other segments or leading our own team enablement sessions.

What advice would you give to someone who's looking to manage teams? 

Be trusting, have transparency, and remember that people are more than just a number. I firmly believe that great companies put people first and if you're ever interested in something new, you should try it. There will be leaders that you can lean on and typically, you know more than what you may give yourself credit for. I feel extremely grateful for the opportunities that I've had to grow my career at Box and I owe a lot of that to the people who believed in me along the way. I'm excited to help other people advance their careers to build toward what's next.

Thank you, Caroline, for taking the time to be a part of our Boxer Spotlight series. We look forward to seeing what you'll do next at Box!