Bookkeeper360's 10 Year Anniversary

Words from our CEO, Nick Pasquarosa:

In October 2022, Bookkeeper360 turned ten years old. Leading into this milestone, I had a mix of emotions and flashbacks of all of the memories and moments from the past decade. I wanted to do something special and memorable to celebrate and recognize the team's dedication to our mission. After all, expanding the team to nearly 70 team members who support 1,000+ businesses nationwide was and is hard work, and I am so proud of what we’ve accomplished.

If we still had an office in New York with local staff, we would have organized a meetup in our office or at a nearby restaurant. Due to the pandemic, we ditched our office and now have team members in 26 states across the country.

I huddled up with the leadership team, and we discussed flying the team to Long Island, New York, the birthplace of where Bookkeeper360 all started. The idea was daunting and with no one being a professional event planner, hosting a successful event felt unachievable. Not to mention the concerns about the costs we were estimating and the downtime of being unable to service our customers for the week.

Once we committed to hosting the summit, we organized a planning committee. We discussed everything from flights, hotels, conference spaces, team-building exercises, and coaching consultants to ensure this trip was worth our team's time away from their families and clients. We wanted a balance between team-building, fun activities, aligning our team with our company's strategic objectives for the upcoming year, and improving our skill sets. We also decided to use Divvy Card, an expense management solution that helped us virtually generate credit cards for our team members to use to book travel.

We decided to start the week by flying in our managers and leadership a few days early to participate in a handful of workshops. I’m a firm believer in “people leave managers, not companies,” so we felt it was a great use of time to invest in connecting all of the team and department leaders. Together we did deep dives into our business model, had thorny debates, and did exercises like a S.W.O.T analysis, and we collectively had a lot of takeaways. We learned about and discussed topics that no Google Meet or Zoom could ever accomplish.

As the rest of the team started flying in, I will never forget the feeling, and I was eager to meet most of the team for the first time in-person and nervous about ensuring everything went perfectly.

Our team experienced some travel delays. One of our team members had to take a midnight train from Washington, DC, to New York after two flights were canceled. Another had to rent a car from Massachusetts and drive to Long Island after her flights were delayed numerous times. Even with travel delays, our team's resilience to get here to celebrate this milestone together really amazed everyone.

We kicked off the summit with a welcome reception, which was surreal. Our team instantly attracted like magnets, taking selfies and connecting for the first time in-person. At one point, “wait staff at the venue asked where our office is?” I laughed and said we were all remote. Despite being remote, all working from our home offices located thousands of miles apart, our culture kept us connected. This level of interaction was a lot for some people, and I could tell, especially some of our introverts at the company. One team member came up to me and said, “This is amazing, but too much for me, too many people; I’m not used to this!” as she left the reception to catch up with some client emails back in their hotel room.

The rest of the week, we learned about our communication styles and did a personal communication assessment (where I scored a 29 Red and 29 Green for anyone that knows what that means). We had a tower-building competition using spaghetti, marshmallows, and string as building supplies, competing for first-place bragging rights. We also invited our customers and had a fireside chat, where they shared their entrepreneurship journey and how Bookkeeper360 has helped them along the way.

On our last night, before everyone had to catch their early AM flights back home, the team navigated their way to the hotel restaurant, and we played Baggo (aka Cornhole) for one last hurrah. One memory I will never forget is something I saw from the corner of my eye. I noticed a company laptop with two external monitors on one of the tables in the restaurant. And it was the same team member that left our welcome reception just days before due to the overwhelming social situation; they had set up their space and wanted to be surrounded by their work family on the final night while crunching through spreadsheets and reconciling a client's accounting. I smiled and was assured that this was a successful week.

I hope this article was insightful and encouraged leaders of other remote companies to invest in their people and have local meetups; our team’s experience was extraordinary, and yes, we plan to do it again.

If you’re interested in joining our team, visit our careers pagefor opportunities and more information.