The learnings are based on our recent webinar, “Inside Reddit’s IT playbook for AI and scale”. Check out this session and other conversations with customers on-demand.
When Reddit grew from fewer than 400 people before 2020 to roughly 4,000 globally distributed employees today, it wasn’t just their headcount that changed. The mandate for IT changed with it.
IT used to be a function that could “run the technology show in a dark server closet,” as Reddit Deputy CISO and Head of Corporate Engineering Sean Joerg put it. But IT has now become the glue that holds business processes, communication, and data together. In the AI era, that glue is under more stress than ever.
In a recent session, Joerg walked through how Reddit’s IT and security teams became AI-ready by modernizing their system of work. Their journey offers a practical playbook for IT leaders looking to scale, reduce tool sprawl, and unlock AI without losing control.
These three objectives are at the core of Reddit’s IT and security teams:
- Modernize at scale with a standardized system of work
- Build governance and guardrails that enable safe experimentation
- Get AI-ready by centralizing knowledge and driving cross‑functional buy‑in
Along the way, Reddit expanded its use of the Atlassian Teamwork Collection, powered by Rovo for support, and also leaned into Loom for more effective communication through video.
Modernization at scale
By the time Reddit reached 1,000 employees, the old ways of working had hit a wall. Teams were scattered across tools, time zones, and inconsistent processes.
“The ways that Reddit used to work five, six years ago truly don’t scale to 4,000 globally distributed employees… You’re suddenly interacting with a team that sits four or five time zones away. How do you effectively manage work between those disparate time zones?”
–Sean Joerg, Deputy CISO and Head of Corporate Engineering, Reddit
Early on, engineering had largely standardized on Jira. Business teams, however, were using a patchwork of task managers and collaboration tools. That fragmentation created exactly the problems most IT leaders recognize:
- Siloed verticals that didn’t align with shared business outcomes
- Tool-specific workflows that were hard to connect across functions
- Data scattered in different systems, making metrics and reporting painful
Consolidating onto a shared system of work
Joerg’s team made a deliberate choice: consolidate on the Atlassian System of Work and expand the Teamwork Collection beyond engineering to business teams like marketing and sales.
This wasn’t just a procurement exercise. It was an opinionated shift in how work should happen:
- Move business task management into the same platform as product and engineering to make planning and execution visible end-to-end.
- Showcase business outcomes in the same place where work is tracked, so teams see how their plans connect and where dependencies live.
- Lean into opinionated patterns for how to collaborate, rather than letting every team reinvent its own model.
“Some of the problems that may arise come from the fact that folks have too many opinions, but no one central thought in terms of how something should function… As an IT leader and as an IT organization, oftentimes the business is actually looking for you to have an opinion.”
–Sean Joerg, Deputy CISO and Head of Corporate Engineering, Reddit
That opinion showed up not only in the tools Reddit standardized on, but also in how they were configured.
From team-managed chaos to company-managed scale
Even after standardizing on a core platform, Reddit carried cloud-era tech debt: a long tail of team-managed projects, one-off workflows, and sprawling labels and components that slowed change down.
About two years ago, IT made another big move: migrating to company-managed projects at scale.
On the surface, that might sound like taking control away from teams. In practice, it did the opposite.
“[Moving to company-managed projects] actually gives most of the teams far more capability and control in terms of how they administer and manage their projects more directly. It also eliminates a lot of the burden for us from a change management perspective.
That’s been a huge uplevel both for my team, but also the teams that are leveraging Atlassian more directly today.”
–Sean Joerg, Deputy CISO and Head of Corporate Engineering, Reddit
By moving from team-managed projects to company-managed projects, Reddit’s IT teams:
- Reduced workflow, label, and component sprawl so changes no longer required “load balancing” across dozens of slightly different configurations
- Enabled more consistent building blocks for business teams, so marketing and sales could get started with out-of-the-box patterns instead of designing everything from scratch
- Freed time for high-value partnership from IT, since the team wasn’t stuck performing one-off admin tweaks for every team-managed project
For IT leaders, the takeaway is clear: modernization at scale isn’t just about picking the right tools. It’s about establishing a shared system of work that teams recognize, trust, and can extend without breaking everything else.
Enabling safe experimentation in the AI era
As AI accelerates change, IT and security teams are forced to rethink how they govern.
At the same time, many teams still need room to go off-path and experiment to keep up with AI’s evolving landscape. That tension is most visible in security: old risk aversion can no longer serve as the default brake on questionable tech decisions.
Because the business now accepts more risk for speed, leaders must define clear guardrails, enable safe experimentation, and maintain a paved path to production. In that environment, saying “no” isn’t a sustainable strategy. Reddit’s approach combines paved paths with intentional “side quests”.
Securely balancing paved paths and side quests
Joerg described a familiar pattern in technology governance:
- Paved path: well-defined platforms and patterns are blessed for mainstream use
- Guardrails: policies, security controls, and operating models that keep teams within acceptable risk bounds
- Off-path experimentation: limited spaces where teams can explore new capabilities before they’re fully standardized
For AI, the balance needed to shift. Reddit’s IT and security teams leaned into:
- Clear governing functions around data exposure, supply chain risk, and regulatory/compliance needs
- Tiered guardrails that distinguish between high-risk and lower-risk experimentation
- Explicit paths from side quests back to the main quest, so promising experiments can be rationalized into the official system of work
For IT leaders, this is the emerging pattern of AI governance: hold firm on risk fundamentals, but create controlled lanes for experimentation so teams don’t go completely around you.
Centralizing knowledge and preparing people to maximize AI’s impact
Reddit didn’t start its AI journey by buying an agent and hoping for the best. Instead, Joerg’s teams focused on the fundamentals that make AI and automation useful: clean knowledge, clear processes, and deep trust with the business.
Centralizing knowledge and processes for Rovo
Reddit moved IT and security support to Rovo as the primary agent surface. They had previously used another bot as “training wheels” to help the organization become comfortable with self-service. When they moved to Rovo, they paired that change with deliberate work on documentation and process.
Joerg’s checklist for making Rovo effective:
- 🧾 Centralize operational documentation in Confluence. Move from scattered pages to a single, reliable source of truth.
- 🔁 Keep documentation current. Make sure pages reflect how the work actually happens today.
- 📚 Codify key processes. Capture steps clearly so anyone can understand and follow them.
- 📡 Connect Rovo to the right channels and portals. Let people ask their real questions, then track where Rovo can successfully resolve issues.
The impact:
- A smarter, centralized support bot that Reddit employees actually enjoy using
- Faster answers, with more natural conversations and more purposeful direction than their previous bot
- A single, AI-ready knowledge base that powers both human productivity and automation.
Loom as a knowledge amplifier
Reddit’s AI-readiness isn’t just about structured tickets and docs. It’s also about the informal, human knowledge that lives in the organization.
Loom emerged as a surprisingly powerful part of that system.
A few patterns stood out:
- “Could this have been a Loom?”
Joerg has flipped the classic “Could this have been an email?” question into something more human. He would rather record a quick Loom than write a long email that fails to convey tone, nuance, or emotion.
“When I have something to write or I have a presentation to create, I will actually just go and record a Loom of the things I want to say and then take the transcript of that and then use Rovo or another agentic tool to coalesce this into a narrative. That saves a ton of time. Loom is a really powerful product for us.”
–Sean Joerg, Deputy CISO and Head of Corporate Engineering, Reddit
- Faster communication with higher engagement
“Nobody actually likes email,” he joked. “Video engagement is always much higher. I’d much rather watch a person showing me something than spend five minutes on an email.”
Together, Rovo and Loom illustrate what “AI-ready” looks like in practice: people working in ways that are naturally captured, searchable, and reusable, with agents seeded by high-quality, contextual knowledge.
Building trust in IT as the foundation for change
Underneath Reddit’s system-of-work modernization and AI-readiness efforts is one core metric Joerg pays close attention to: trust.
“One of the biggest things that tells me if we’re doing well is the willingness of the company or individuals at the company to come to IT and ask for help. And I’m not talking just about technology-specific questions, any question.”
–Sean Joerg, Deputy CISO and Head of Corporate Engineering, Reddit
That signal tells him three things:
- IT responds well and shepherds questions effectively.
- Stakeholders trust IT with their problems and feel safe bringing them forward.
- The team is equipped to solve and tackle ambiguous challenges without being intimidated.
That trust is what makes hard changes possible – like consolidating tools, migrating off beloved team-managed projects, or introducing agentic support.
Joerg’s advice to IT leaders who feel overwhelmed by change management and AI disruption is deceptively simple:
- Start with “What can I help unblock today?”
- Deliver visible wins that meet teams in the middle, without sacrificing security or compliance.
- Use those wins to expand your influence and shape the work system your org needs for the next wave of change.
“Don’t sacrifice security. Don’t sacrifice compliance. Those are the underpinnings to how you operate. Find the flexibility to meet teams in the middle. That’s going to do so much for building trust and for your capability to offer solutions you can support long-term.”
–Sean Joerg, Deputy CISO and Head of Corporate Engineering, Reddit
What Reddit’s journey means for IT leaders
Across Joerg’s stories, a consistent pattern emerges–one that maps directly to what many IT leaders are wrestling with today:
- Tool consolidation is not just a cost play. It is how you create the unified, opinionated system of work that enables and sustains AI adoption.
- Governance and guardrails are evolving. You still need paved paths and strong controls, but you also need sanctioned side quests where teams can explore AI without putting the business at undue risk.
- AI-readiness is built on shared knowledge and trust. Centralized documentation, organic Loom libraries, and a culture of going to IT for help make agentic tools like Rovo effective.
As AI advances in days rather than months, organizations that have already laid this groundwork will be the ones that can adapt without breaking.
Reddit’s experience shows that becoming AI-ready is less about chasing the latest model and more about modernizing how your teams work together: one system of work, shared guardrails, and a culture where IT is the trusted comrade in every business objective. Learn more about how Reddit uses Loom and their success with Atlassian Teamwork Collection.
