How Datasite cut 4,000 meetings and built a culture of time empathy using Loom

The learnings in this blog post are based on Datasite’s session presented at Atlassian’s Team Europe ’25 conference. You can check out this session and others on demand.

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If your calendar currently looks like a game of Tetris, you are not alone. At Datasite, leaders regularly faced double- and triple-booked days where every meeting felt important, and there was no clear way to reclaim focus time. Collaboration was happening, but at the expense of deep work and energy.

Instead of adding yet another tool to the pile, Datasite used Atlassian’s Teamwork Collection to change how work flows through the organization. By leaning heavily into Loom and pairing it with Jira, Confluence, and Rovo, Datasite reduced more than 4,000 meetings in five months and saved roughly half a million dollars in meeting time.

Underneath those numbers is something even more important. Datasite has nurtured a cultural shift toward what EVP of Product Operations and Enablement JR Harrell calls “time empathy,” where people actively choose async communication before reaching for the meeting invite button.

Datasite’s Loom wins at a glance:

• Cut more than 4,050 time-consuming meetings in the first five months
• Reclaimed roughly $500,000 worth of meeting time
• Accelerated Jira bug tickets due to additional context provided through Loom
• Achieved 29% organization-wide Loom fluency

The collaboration challenge at Datasite

Datasite powers high-stakes M&A (mergers and acquisitions) by moving vast amounts of sensitive information through its ultra-secure platform, so meetings became the default way to stay aligned.

Over time, that default created a serious drag on productivity. Harrell’s days were filled with overlapping meetings and almost no space for deep work, and he found this pattern across the organization. This was not a personal time management issue but a systemic collaboration problem.

The solution was not simply “fewer meetings” but a different way of working that still preserved rich context and connection. Async communication had to feel as natural and effective as live conversation to prevent people from reverting to old patterns.

Choosing Atlassian’s Teamwork Collection as a new system of work

At the time, Datasite was already a strategic, cloud-first Atlassian customer using Strategy Collection. To address their collaboration challenge, they added Teamwork Collection, bringing Loom, Jira, and Confluence together into a single, connected platform powered by Rovo. Loom quickly became the front door to Datasite’s new, asynchronous way of working, but its impact depended on how it was rolled out.

An MIT Sloan study confirmed what Harrell’s calendar already showed: meetings were consuming most people’s time without delivering enough value.

Knowing that change management is best started from the top, Harrell committed to modeling asynchronous behaviors personally. He began sending Loom videos in situations where he previously would have scheduled a call, and he asked peers and teams to do the same. This early buy-in from other executives, including Datasite’s Chief Product Officer, helped the new behavior spread.

Removing friction was equally important. Loom access was set up so that if someone received a video and did not yet have an account, they were only a couple of clicks away from signing in with SSO. It felt far closer to a consumer experience than a complex enterprise rollout, which reduced resistance to trying something new.

After that, the foundation was in place, and Datasite used a deliberate adoption framework. Harrell leaned on the “Crossing the Chasm” model, focusing first on innovators and early adopters within the company, then using training and analytics to sustain the momentum in the mainstream. That gave the rollout a clear path from early excitement to broad, sustained use.

How Datasite actually uses Loom with Jira, Confluence, and Rovo

The real power of Teamwork Collection at Datasite comes from the way Loom weaves through Jira and Confluence in everyday workflows. Rather than existing as a separate video island, Loom recordings live right where work is already tracked and discussed.

Jira x Loom

Loom adds context to Jira tickets

In Jira, Loom helps make work items more precise and faster to move. Text-only bug reports and user stories can be surprisingly ambiguous, even when they are carefully written. Harrell’s teams routinely embed short Loom videos directly into Jira issues so developers can see and hear what is happening. Since most people speak faster than they type, it is easier to walk through a bug, show the exact steps, and narrate the nuance that would normally be lost.

Use Loom to auto-generate a Jira bug report

One of Datasite’s favorite examples is their bug reporting workflow. A product marketer who noticed an issue in an app recorded a Loom instead of writing a bug ticket from scratch. From that recording, Loom automatically created a structured Jira bug report. A Rovo agent then scanned the new ticket to check whether it met Datasite’s standards and flagged any gaps. That combination of Loom, Jira, and Rovo cut out much of the manual effort without sacrificing quality.

Confluence x Loom

In Confluence, Loom turns static documentation into a richer, more accessible experience. Teams augment pages with short videos that explain a feature, walk through a process, or provide background on a decision. Loom’s transcripts are indexed in the teamwork graph, so Rovo can surface those videos as answers when someone asks a question. Over time, this has created a library of reusable, multimedia knowledge that teams can tap into without scheduling yet another walkthrough meeting.

Meeting habits have changed as well. Datasite used to bring around 125 people to a monthly business review call. That meeting still exists, but only for a small group of key leaders. They record the full discussion in Loom, then Rovo helps distill the most important topics. The Head of Product records a short recap on Loom, typically around 15 minutes, which becomes the primary artifact for the wider audience. Instead of asking over 100 people to sit through a 2-hour call, Datasite asks them to watch a targeted summary and follow up asynchronously where needed.

– JR Harrell, EVP of product operations and enablement, Datasite

The same pattern now applies across many recurring meetings. Loom and Rovo capture, summarize, and connect the content. Jira and Confluence capture the decisions and follow-up work. As a result, individuals can stay informed at times that fit their schedules while still benefiting from the richness of spoken conversation.

Fewer meetings, more focus, and time empathy

Within the first five months of this approach, Datasite offset more than 4,050 meetings. Using reasonable assumptions about average meeting length, the number of participants, and hourly cost, that translates to roughly $500,000 in reclaimed time.

Today, 11 teams at Datasite use Loom alongside Jira, Confluence, and Rovo as part of Teamwork Collection. About 29% of their Loom users are regular recorders, which places them in what Loom considers “gold star” territory. The bigger payoff, though, is in how many people watch, reuse, and reshare those videos across the organization.

Loom has even become part of the everyday vocabulary. According to Harrell, Datasite employees now say things like “I will Loom that to you in a bit,” a sign that async communication is now the default rather than an exception. Work keeps moving while people travel, attend conferences, or step away from their desks, because updates and decisions can continue on Loom threads instead of waiting for the next free calendar slot.

Most importantly, this shift has changed how people think about each other’s time. Before, it was normal to drop a half-hour or hour-long meeting on a colleague’s calendar without much thought about the impact on their focus. Now, people pause and ask themselves whether a meeting is truly necessary, whether it will serve everyone involved, and whether a Loom might be a better way to share context or make a request. That habit of reflection has spread across teams, making collaboration feel both kinder and more effective.

Practical tips you can borrow from Datasite’s journey

If your organization is wrestling with too many meetings and a need for better async collaboration, Datasite’s experience offers several practical lessons. You can adapt these ideas to your own context, even if you are only beginning to explore Teamwork Collection.

Start by treating this as a change in how you work, not just a software rollout. Leadership modeling is critical, so have senior leaders commit to using Loom ahead of or instead of meetings in visible ways. Pair that with low-friction access, and you will remove two of the biggest early barriers.

Think next about where Loom can plug into your existing tools rather than sitting on the side. Embed short Looms into Jira tickets where context is often hard to capture in text. Add Loom walk-throughs to Confluence pages that you know people struggle to understand from words alone. Make sure Rovo indexes your Loom transcripts so those videos become discoverable, reusable assets in your teamwork graph.

Finally, give people explicit permission to question meetings. Encourage them to ask whether a scheduled call could instead be a Loom update that colleagues can consume on their own time. When they schedule a meeting, suggest they record it with Loom and use Rovo to create a concise recap others can access later. Over time, this combination of tools and norms can help your teams build the same kind of time empathy that is now taking root at Datasite.