Maintaining a Remote First Culture Using AI: Tremendous Case Study

December 28, 2023
Alyssa Schwartz
Alyssa Schwartz
Remote first culture using AI
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Tremendous takes the stress out of sending payments at scale, worldwide, by making it easy to send one or thousands of payments to people in over 200 countries. 10,000+ companies like Google, MIT, and United Way have trusted Tremendous to send over $1 billion in payments. 

The details:

Number of employees: 85

Industry: Financial services

Tech stack: Slack, Google Docs, Asana, Notion


At Tremendous, the employee experience has been central to the company’s growth and identity. Employees are fully remote, and the company emphasizes mindful communications and interactions over spending hours in meetings where nothing gets done.

It’s an approach their employees love. But pulling it off requires careful thought, specifically around the types of tools people use as well as where information lives and how workers can access it.

As with many remote first organizations, Slack is a lifeline where workers can ask questions and share information. But it produces other challenges as well.

 For starters, when someone asks a question on a shared channel, it can take time for a colleague to chime in with the answer, creating occasionally frustrating delays. Additionally, an endless stream of even “quick” questions are a distraction for everyone on the thread. The company knew that the problems could be circumvented if employees had the tools to quickly find what they needed themselves.

“We have a lot of information stored in different places,” says Sarah Gabr, Director of Operations at Tremendous. “A lot of context behind historical decisions is spread across various Slack channels, or nested in threads. We also  have a handful of documentation repositories for distinct areas of the business.” 

“Things like operations and legal compliance are in Google Docs. Product work and product decision-making tend to be in Notion. So if you have a question about something that involves both the product and the operations teams, like a question about an agreement with one of our card vendors, it can be hard to find,” she says. 

Leveraging innovation in the AI space

“Maintaining a remote first culture requires visibility,” says Gabr. “We need to offer a high degree of information access, transparency, and documentation.”

That meant an enterprise tool that could surface knowledge quickly. But with large volumes of ever-evolving conversations and content, not just any tool would do.

“The first vendors we tested were more like information centers, where we could upload documents and then search across them,” says Gabr.

 “That wasn’t helpful. We wanted a tool that searches and consolidates our information surface area. With all the innovation happening in AI, we ultimately wanted to find something that could synthesize all our sources and surface the right information fast.”

Dash AI’s quality of answers rises above

Dashworks delivered on Gabr and team’s requirements.

“What made Dashworks stand out was the quality of answers,” Gabr says. “We found Dash AI to be impressive. No matter what you asked it – whether you wanted specific information or a summary of what you worked on the week prior – its output was valuable. People were amazed.” 

Dash AI has since become the go-to for questions and information. “People aren’t blowing up Slack and making it noisy for everybody else looking for information that already exists. When you do get questions in a channel, it’s much more informed, because everyone has context.”

The ability to easily access the right information has improved operations in other ways too, such as onboarding new employees. “Someone who just joined the company can ask questions they might not be comfortable enough to ask in a public channel,” Gabr says. 

Another use case is supporting on-call engineers.

“We have Dashworks linked to Asana, which is where we keep our engineering tickets,” says Gabr. “Now, when someone on support gets a ticket and it sounds like something that’s been fixed before, they can go into Dashworks and quickly find out how.” 

“We all really like that Dashworks doesn’t just give you information. It shows you where it got it from,” Gabr says. “We’re not just blindly trusting what it says—it’s easy to double check everything.”



“One click and you have access”

Dashworks’ browser plugin and ability to instantly connect to Slack and other apps via API made implementation of their enterprise knowledge assistant “super easy.”

“The fact that each employee can manage their own access and permissions via Chrome makes it convenient. Every time I want to add a new application to Dashworks—whether that’s Hubspot or Slack or Notion or Google Docs—that’s also simple. One click and you have access.”

Pro tip

“The more of your content and apps you can hook up to Dashworks, the better,” Gabr says. “I’ll upload documents I frequently have to reference into Notion so that Dashworks can search it. Then when I have a question, I can ask Dash AI instead of reading through 20 pages of legal writing to arrive at an answer. Often I know that I have information somewhere, but I can’t remember which page, app, or Slack thread it originates from. By making a point to document it in an app that’s connected to Dashworks, I can find what I need, regardless of when I created it.”


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