JJ Reeder, former Director of Remote Organizational Effectiveness at Upwork, is leading the charge in revolutionizing knowledge management for remote-first organizations. This April at Running Remote 2025, she’ll share insights in her session, “Handbooks on Steroids: In the Age of AI, Knowledge Management is a Make-or-Break Strategy,” exploring how AI-powered, dynamic knowledge bases are transforming collaboration, efficiency, and innovation in the workplace.
Handbooks on steroids: in the age of AI, knowledge management is a make-or-break strategyWhile the rest of the world was treating company handbooks as nice-to-haves, many digital-first organizations invested in robust, living knowledge bases. Then came AI – and suddenly, companies with a searchable archive are set up for massive gains in efficiency, collaboration, and innovation. Here’s what the handbook of the future looks like, and how to invest wisely in yours.
Before joining Upwork in 2022, where she helped transform its global team into a premier remote-first organization, JJ Reeder built extensive expertise in remote work environments. Her career spans roles at fully distributed companies like Toptal and GitLab, where she focused on creating high-performing global teams. With a master’s degree in Industrial-Organizational Psychology from Harvard Extension, JJ combines practical experience with research-backed strategies to enhance meeting effectiveness, promote transparency, and develop flexible benefits tailored for today’s distributed workforce.
Upwork is a remote-first company, embracing a distributed work model that allows employees to work from various locations globally. This approach aligns with Upwork’s mission to create economic opportunities so people have better lives. The company has been proactive in developing strategies to manage remote teams effectively, emphasizing clear communication, robust remote work policies, and a strong organizational culture.
Incorporating artificial intelligence (AI) into its operations, Upwork utilizes AI to enhance various aspects of work. This includes automating repetitive tasks, improving project management through AI-powered tools, and leveraging AI for research and analysis to support decision-making processes. The integration of AI aims to streamline workflows, increase efficiency, and foster innovation within the company.
As organizations navigate the complexities of remote work, the need for efficient knowledge management has become more critical than ever. Ahead of her session at Running Remote 2025 in Austin, “Handbooks on Steroids: In the Age of AI, Knowledge Management is a Make-or-Break Strategy,” we sat down with JJ to explore how AI is reshaping knowledge systems, the key to unlocking productivity gains, and what companies must do to future-proof their remote-first strategies.
In your role at Upwork, what specific strategies have you implemented to transform the company into a best-in-class remote-first organization, and what challenges have you encountered during this transition?
First, let me say that I have been part of a big movement at Upwork – the credit is shared with many of my colleagues and with my team. Transformation work requires coordinating change across many fronts, and I was lucky to encounter quite a few people who know their stuff and take every opportunity to move toward the future of work.
Upwork was also well along the path when I joined, due to the longstanding practice of engaging global talent from its network. Many people had been doing their work remotely and across time zones for years, long before the company officially went remote-first.
However, there was an appetite to push for more: better async-first communication and collaboration, new ways for people to manage their work independently, and cultural pillars that would support a self-sustaining team dynamic across all the countries represented in Upwork’s workforce.
The first phase of our transformation was upgrading some of the foundational elements that drive healthy async-first communication, collaboration, and culture. We revisited the company values, published new values grounded in behavioral science, and baked them into every key process. Next we looked at how information flowed throughout the company: we retired an old learning system and launched a tech-forward intranet that’s user-friendly and highly searchable, and gave us new ways to communicate and connect internally. We also looked at performance and goal management, and built a goal-tracking system that supports better reporting throughout each quarter, supporting managers to refocus on results and outcomes.
The next phase was providing a vision orientation, clarity on the strategy, and a more transparent set of behavioral expectations. We built an operating model grounded in philosophical principles and supported via strategic priorities. Then we created a clear set of guidelines for each team member to understand how work gets done, and what they can expect. That covered everything from meetings (especially when not to have one), to internal awards programs, to time management and project management.
I’m blown away by how much we were able to accomplish in just two years to transform the organizational infrastructure. The challenges were what you’d expect: this work requires a leap of faith at times, and between the first step off the ledge and your landing on solid ground, it can be chaotic. But as anyone who’s done organizational transformation knows, chaos is just one part of change.
How is Upwork leveraging AI to transform its internal knowledge management systems, and how does this align with your concept of ‘handbooks on steroids’ in revolutionizing how companies manage and utilize their knowledge bases?
The most effective and efficient way to incorporate AI today is by layering it directly into systems you’re already using – literally add an AI agent to your source of truth, so it can help you search, compile, and automate. Upwork partners with vendors like Haystack (intranet) and Asana and Jira (project management). All of these partners are tech-forward, always evolving, and consistently rolling out AI features and improvements.
In practice, what this means is: the company laid the groundwork through a teamwide effort to standardize its knowledge repositories. Upwork has all of its documentation and work in a few core locations. Introduce an AI agent, and it can do things like:
- Answer team member queries via a search interface that returns not just the answer to the question, but links to the resources the information it was pulled from – just how Google Gemini works in your web search.
- Automate projects and tasks across multiple systems so project docs are kept up to date, the right people are notified, and records are more accurate.
- Summarize progress and status of projects on a regular basis, sending out automated reports that become part of the record of what got done, when, and by whom.
These are all AI-driven features that are available and active right now, and they all cut through the clutter and help us create better information and share knowledge on demand.
Ultimately, information should be standardized, current and accurate, and available to anyone on demand. That’s the outcome of a high-performing knowledge management system, and AI is helping us get there.
What advice would you offer to organizations looking to invest in AI-driven knowledge management systems to ensure they are making wise and effective investments?
I’ll tell you what NOT to do: don’t bother trying to set up an internal AI chatbot if you don’t already have a great internal knowledge base for it to pull from.
And be very wary of using an AI generator to build your knowledge base on the cheap.
GenAI is very young, and right now, it’s mostly being layered on top of systems (as in the examples I shared). In a few years, we’ll see more potential for truly AI-driven, robust tools; however, it’s going to take some time for these tools to come online in a meaningful way.
The first thing any company should do is assign an expert to the task of building a robust library of internal knowledge (see my guide to handbooks for more). That’s still the best investment you can make: pull together all the knowledge you already have!
Then, invest in a system that serves your people. It should be user-friendly, tech-forward, human-first. Understand your vendor’s AI strategy and roadmap, and be sure you’re building out your knowledge in a way that can eventually leverage GenAI. But always remember: your users are people, not bots.
How do you foresee the role of AI evolving in the context of remote work, particularly concerning organizational effectiveness and team collaboration?
I’d like to see AI agents embedding in remote organizations to strengthen connective tissue, reinforce ways of working, and support handoffs.
Vision: an internal agent that helps build connections throughout the team by introducing people natively on a chat platform (like Slack). The agent can be prepped with people’s shared interests, and/or it can be tasked with building collaborative tissue between parts of the organization. There’s a big project coming up that will require great communication between Marketing and R&D; the AI agent identifies connection points and ensures people build the relationships they’ll need.
An agent like this could also monitor communications and nudge people when they don’t communicate effectively, or remind them to share updates. I don’t want to recommend anyone should build a NagBot, but well-placed nudges, used sparingly throughout a team, can quickly create efficient and consistent behavioral trends.
Finally, an agent like this could fully automate work handoffs across time zones: summarizing the work done before your day started by teammates around the world, and informing you of the priorities and next steps. Clean handoffs are key to async, and they’re incredibly difficult – for humans. It’s a perfect use case for AI.
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What can people expect from your session at Running Remote this April in Austin?
In all the GenAI hype, a lot of companies are missing the core idea: how are you going to integrate AI into the business in a deep, meaningful way?
My mission is to get leaders thinking and acting in ways that will future-proof their companies. I’m here to equip you with new tools and ways of thinking – especially about the transformative elements that are right in front of you, but may be overlooked. We’re going to talk about the factor that I believe will unlock the next wave of organizational AI – an asset that most companies really aren’t leveraging at all – their source of institutional knowledge.
We’ll talk about why some companies are already primed to leap ahead in efficiency and productivity, while others are potentially setting themselves up for disaster or wasted effort. And I’ll share what we know so far about building a powerful, AI-ready library of information.
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Why You Should Attend Running Remote 2025
The way we work is changing fast. Remote and hybrid teams need smarter strategies to stay efficient, innovative, and connected. That’s where Running Remote 2025 comes in — the world’s leading event on remote and distributed team leadership. Taking place this April in Austin, Texas, the conference brings together top experts and forward-thinking leaders to help future-proof your business.
Here’s why you should be there:
✅ Learn from Industry Leaders
JJ Reeder’s session is one of the many highlights of this year’s lineup. With over 50+ speakers, and dedicated networking opportunities, this event equips attendees with actionable insights and tools to thrive in a remote-first world.
✅ Unlock Practical Insights on AI
JJ highlights in her interview how AI is reshaping the way organizations manage knowledge — automating workflows, enhancing collaboration, and making key information instantly accessible. At Running Remote, you’ll learn how to integrate these tools into your own company and stay ahead of the curve.
✅ Connect with Like-Minded Leaders
Running Remote 2025 isn’t just about learning; it’s about connecting. With dedicated networking sessions, you’ll meet business leaders, HR professionals, and remote-first founders who are shaping the future of work and gain valuable insights from their experiences.
Be Part of the Future
If your business is navigating the challenges of remote work, this event is your chance to get actionable strategies, meet experts, and stay on top of emerging trends in distributed work and other topics like AI.
Don’t miss out on the opportunity to future-proof your team at Running Remote 2025! Join us in Austin on April 29-30, 2025, and be part of this transformative journey. Secure your Spot
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Register Now for Running Remote 2025
