How Trail of Bits’ Collaborative Nature Breaks Barriers

Team members describe how the security software company fuels cross-functional collaboration through transparent communication, knowledge-sharing and connection.

Written by Olivia McClure
Published on Jun. 30, 2023
How Trail of Bits’ Collaborative Nature Breaks Barriers
Trail of Bits
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When Security Engineer Joe Sweeney joined Trail of Bits, he had never seen a company quite like it before.  

Having worked at companies where it was hard to converse with people across departments, he was struck by the organization’s focus on cross-functional collaboration. He could see how this cohesion made work so much easier. 

“The culture of the company makes communication painless, as there isn’t anyone in the company that I would hesitate reaching out to,” Sweeney said. 


“There isn’t anyone in the company I would hesitate reaching out to.” 


Despite steady growth over the past few years, Trail of Bits has maintained its focus on tight-knit teamwork. According to Senior Security Blockchain Engineer Nat Chin, that’s because collaboration defines the nature of how team members operate. 

“It’s common to find teams consisting of individuals with a diverse set of experiences working together,” she said. 

To ensure employees continue to share knowledge and support each other as Trail of Bits grows, the company adheres to core practices that drive both teamwork and connection. 

“Ensuring our processes remain efficient as we scale is a priority,” said Recruiting Coordinator Amanda Santos

Through transparent communication, knowledge-sharing and connection, team members across Trail of Bits are empowered to collaborate on cutting-edge projects with the potential to redefine the security space. 



Trail of Bits is a cybersecurity research and consulting firm offering services designed to “deepen the science of security” for some of the world’s most targeted organizations and devices in the defense, tech, finance and blockchain industries. Its clients’ dedicated security teams come to Trail of Bits for needs such as auditing products or networks, consulting on modifications necessary for a secure deployment or developing features that close their security gaps.


Team photo
Trail of Bits


Transparency Comes First

Although it’s not a workplace practicing “radical honesty,” when it comes to having important conversations, teams at Trail of Bits do prefer to keep things out in the open. 

“We keep conversations around projects in public channels as much as possible to allow anyone else on the team to pop by, follow along, help out or chime in,” Chin said. She further explained that, given the diverse expertise across the company, it’s important to have low barriers to conversations, allowing team members to share important knowledge. 


“Given the diverse expertise across the company, it’s important to have low barriers to conversations, allowing team members to share important knowledge.”


Chin added that the company encourages teams to keep information in a centralized location, which is especially helpful for new team members and cross-functional partners. By having access to ongoing challenges and wins, employees can learn from each other and offer help more effectively. 

Transparent communication also plays a significant role in supporting employees’ professional growth. Chin said that team members take time at the beginning of every year to craft a set of goals that align with skills they wish to develop over each quarter. This helps managers understand what a team member wishes to learn and allows them to look for opportunities that will help them hone these skills. 

Managers track employees’ progress through regular one-on-one meetings, giving team members time to adjust or refine their goals. “This per-quarter goal reflection helps with monitoring and ensuring that our employees are given the opportunity to develop in the areas that they want to,” Chin said. 

Santos believes having a core set of communication channels has also fueled successful collaboration across the company. While Slack makes it easy to share information with peers across the globe, monthly town halls enable team members to hear directly from leaders to receive updates. 

The relationship between managers and their direct reports plays a significant role in driving effective communication. Santos noted that managers invest time into sharing updates, encouraging ideas and, most importantly, asking for feedback. All of these efforts help team members stay aligned and find the best solutions to any challenges they may be facing. 

“Managers then work with the leadership team to address any concerns and ensure Trail of Bits remains a great place to work,” Santos said. 



  • A Team Of Highly-Effective People (our people): We aim to build a team of the most talented, experienced, and effective people in our industry. We provide people with agency and full support to solve problems and trust them to do the right thing in complex situations.
  • Complete Trust And Integrity (how we work with clients and publish our work): We build trust with our clients and handle highly sensitive information with complete integrity. Our communications and reports are always accurate and backed by evidence.
  • Open To Sharing Expertise (how we engage with the outside world): We share our technical expertise with the security industry and the public to drive security forward and help the public understand the impact of emerging technologies.
  • Challenging and high-impact work (what we work on): We focus on technically challenging and high-impact work, in areas of high complexity and importance. Our goal is to excel and be the leaders in all areas we choose to work in.
  • Creativity (how we work): We foster an environment of intellectual curiosity, continuous learning and innovation. We are excited about novel approaches to difficult problems.


Team photo infront of Olympic RIngs
Trail of Bits


Breaking Down Barriers

In the spirit of collaboration, it’s common to find team members getting their hands dirty with other departments. Sweeney has worked on multiple projects to help other teams improve their workflows or build new ones. 

“During these projects, I talk extensively with my coworkers to understand their work better so that I can build tools that solve their problems,” he said. 

According to Chin, this cross-functional support occurs across the company. “During projects, subject matter experts always make themselves available to answer questions and help with issues, even if they aren’t assigned to that specific project,” she said. 

Chin added that weekly lunch-and-learn sessions increase visibility into projects, creating space for outside team members to add their input. “Even though we have our core blockchain assurance team, it’s not uncommon for us to work with colleagues on other teams, each of us bringing a different view to the table,” she said. 


“It’s not uncommon for us to work with colleagues on other teams, each of us bringing a different view to the table.” 


Engineers are especially encouraged to take part in projects on other teams so that they can “learn from osmosis.” 

“This gives them a chance to learn about different areas of technology and pick up new skills from their colleagues,” Chin said. 


Office Presentation
Trail Of Bits


Chin noted that, in addition to virtual events, employees take part in two offsites each year — events that are especially powerful due to the fact that Trail of Bits team members work remotely and are spread across more than 30 countries. The offsites, therefore, become a way to get to know a person you may work with frequently but is normally halfway across the world. Chin considers these offsites a “fantastic opportunity to meet people that we work closely with and people on teams where we haven’t had as much exposure.”

Not only do these events help employees build friendships, but they also play a part in breaking down barriers and driving stronger cross-functional collaboration. For Santos, these cultural moments are a testament to the cohesive nature of Trail of Bits, reflecting how often employees connect with each other, whether they’re working on a project or making memories. 

“It can be easy for remote companies to lose a sense of camaraderie that may foster naturally in person,” she said. “I’m proud of how Trail of Bits employees are able to find ways to connect with each other.”


Responses have been edited for length and clarity. Images provided by Trail of Bits.

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