“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX Ep40

Jeff Frick
May 8, 2025
17
 MIN
Listen this episode on your favorite platform!

Jessica “JJ” Reeder was there, with Darren Murph, at GitLab, early pandemic, when suddenly the entire world was interested in their masterpiece, the GitLab Remote Work handbook. When the world was thrown into remote and distributed work over a weekend in Spring 2020, and answers to many of the questions were contained in the tens of thousands of words, and thousands of pages in the GitLab remote work playbook.

As JJ recently reminded, that work started a decade ago. She and Darren are no longer at GitLab, and the Pandemic is 5 years removed and fading in the new rear view mirror. Good news, eyes on the future.

The future is AI-powered. Good news, the same behaviors, attributes, and best practices that powered success in distributed teams, are the same required to increase team AI adoption.

The long held dream of a high functioning organizational knowledge platform, is finally, almost here? 

Please join me in welcoming “JJ” Jessica Reeder to the Work 20XX podcast.

JJ and team are implementing said knowledge platform in her new role at Upwork. As we discuss in this interview, it’s about the hard work, and everyone doing their part, that builds the buy in, and the data base, to dramatically improve the chances of success, wide spread adoption, and a significant reduction in the time spent searching for information.

Thanks again, JJ.

Editor’s Note:
Recorded 2025-April-29 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and the entire Running Remote team for collaborating with Work 20XX to capture these in-person interviews with the top minds shaping the future of work.

Episode Transcript

"JJ" Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX podcast with Jeff Frick, Ep40 from Running Remote

English Transcript

Cold open:
Okay, great.
So, I'll count  us down,
and then we'll go
Wonderful
In three, two, one.

Jeff Frick
Hey, Welcome back everybody. Jeff Frick here. Coming to you not from  the home studio, but Work 20XX  is on the road, and we're down here  in Austin, Texas. Working with the great  folks at Running Remote to do a couple of special episodes down here if you weren't  able to make the trip. And so it's been  an amazing show, they've got a  back to back.  think two stages are going constantly every ten minutes,. Some new expert telling you  more about remote work that you didn't  know before. So we're excited to have our first guest. She's JJ Reeder. She is now the Director of  Remote Organizational Effectiveness at Upwork JJ great  to see you.

JJ Reeder:
Great to  see you too.

Jeff Frick:
Effectiveness I don't know that I've ever seen effectiveness in somebody's  title, I like it.

JJ Reeder:
It is a title. It is, it does exist. Org effectiveness  is a thing. But remote  org effectiveness is really what brings it to that next level. It's, not just about how to have an effective organization, but also how to do that in a distributed environment.

Jeff Frick:
Right So you've been doing this for a long time. We all know you back from the day when you and Darren were writing the original remote work playbook that we all use and share, and has been widely distributed. But your presentation  just now, I thought it was going to be on playbooks, but you really kind of went a different direction on knowledge  management. So how does knowledge management and leveraging  AI and getting that information that's out of the company. How does that tie back to playbooks?

JJ Reeder:
Well, honestly, I mean if you look at the evolution of the company handbook, what GitLab  was doing when GitLab and those companies really innovated  the handbook. That was about ten years ago when they really reinvented what the concept of the handbook was. And it has been continuing  to evolve ever since then. So what it's evolved into is a digital knowledge system. This is a living  system of knowledge that's a key  company asset, represents the knowledge of the entire organization. And so as we continue to have this conversation and as AI enters the picture, knowledge becomes a key company piece of infrastructure almost as an asset. And so we have to start thinking about it in new terms.

Jeff Frick:
Right. So I was just at the Atlassian show a couple weeks ago and they talked about 30%  of people's time is basically looking for information, whether it's I know I have it someplace or I don't know if I have it, I’m trying to find it. And speaking  about inefficiency, you recently posted  about 47 million. Was it hours lost to  searching for information?

JJ Reeder
This is a stat from 2018, actually from Panopto. They estimated that  large businesses lose $47 million per year  per business on average through poor knowledge sharing. And that was 2018. So that is pre-pandemic, pre-AI That's like ancient  history for us. I'm sure that that number has gotten bigger.

Jeff Frick:
Right. So the vision of a unified knowledge base has been around forever. Information locked in, in silos, whether that's departments or laptops or PDF documents or presentations that I'm carrying  around on my phone, have been  around forever. How is it changing now, both as a combination of thinking about a  playbook perspective as well as now  we've got AI, and for AI to  be most effective, it needs access to all those different data sources.

JJ Reeder:
Well, that's the thing. I think that's it. It's the different  data sources. And that's really the challenge right now is that, knowledge can no longer be kept in a bunch of different places. You have to have a single source of truth more than ever before. And we were talking about this back in the handbook days, but but humans were able to sort of make decisions about, you know, which version of something was probably most correct. Or they could  ask one another. As AI enters the scene and as we work faster and faster, it's really no longer possible to have information in a bunch of  different places. And the new conversation is  really about how do we make sure that we are giving an AI agent good information to work from? That means we need a single source of truth. We need to practice good  information management. We need to know that it's  up to date and accurate, because the risks are starting to compound the loss of effectiveness and efficiency is starting to grow. And more and more companies that don't have their  information locked down are going to be left behind.

Jeff Frick:
Right? Right. Because of speed right, speed of decision making, speed of moving  forward, speed of operation,  speed is so critical. You talked about rolling this out at Upwork and trying to help people get the information not only in the departmental silos, but again, off their laptops, where a lot of information lives. And that's why  attachments on emails are one of the many reasons they’re so bad. How did you kind of get a process going? What was your process to start to transfer some of that information to where it's more accessible? Well, so First of all, I think that Upwork was in a really good place compared to a  lot of organizations because they  had really done some of the foundational work to transform transfer the organization to digital operations. And so people were having a good practice of documenting things. But really, what was missing was a way to organize the information. So stuff was in just  all of these different places. We had an LMS, we had a project  management tools, we had a handbook, we had a playbook, we had all sorts of different things. And so really it was about we need to create  a single place where there's  reliable information. And then  to do that, we had to decide what information was  going to go into it. So we started  just thinking about what information are people going to need to understand that  we had to ask We went and had to ask every person at the company, what do you  actually need? You have to make decisions about what  information belongs and what  information doesn't. It's a  long process, but by working bottom up and actually getting  that buy in and getting people  to really understand what this system  would do for them, that really empowered the transition. It made  it possible, and it made it so  that people were really ready to  support it, ready to  engage with it, ready to fill it  with great information.

Jeff Frick:
Right. So it wasn't a new system, right? Was it? Did you pick one as  kind of this is going to be the source of truth we're going to move it into or did you have,  you know, better APIs into some  of the other systems? How did you  approach that?

JJ Reeder:
We picked a new system.

Jeff Frick:
Because you don't want another system or did you?

JJ Reeder:
No. We picked a  new system.

Jeff Frick:
Okay.

JJ Reeder:
We deprecated  old systems.

Jeff Frick:
Well good.

JJ Reeder:
So we picked a new system that had the features and functionality that the team was asking for. We did all  of the research first. We said, what do you need? Then we found something that would hit as many of those  boxes as possible. And then we deprecated the systems that were no longer serving us, moved all the information over, compiled it, fixed it, cleaned it up got people  the information, the permissions and the access that they needed. And then we got rid of the old stuff.

Jeff Frick:
What was the biggest surprise in the process? What was the biggest surprise? Positive or negative I mean, because the other part you talked about is access. And in your presentation just now, you talk about some companies aren't real access friendly and there is  governance and there is kind of a  need to know type of basis depending on  what the project is. So how did you how did you, what was some of the learnings when you were making this move?

JJ Reeder:
Tons of  learnings. There's always  learnings. You know, I think, actually, I'll tell you something that wasn't really what I expected but  it was like a pleasant surprise, which was I,  you know, I had come from  in the past kind of having to talk to the legal team and the trust  and safety team and really make  the case for, like, why we need  this new tool and why we're  going to fill it with all of this  company information, which could be a liability. And I was actually  really surprised that they  already understood at that point they were bought in and they were  totally supportive and they just were like, whatever you need, we will run the  safety checks on it, but we're  ready to go. We understand the importance  of this for the company, because what  they understood is that the bad information  is more of a liability than having your good  information someplace where the wrong person  might be able to see it. Having bad information out there is more of a risk to the company.

Jeff Frick:
Right

JJ Reeder:
So that was a really cool surprise, you know, and then I think  I was surprised by, how quickly people  really got on board. You know, I'm so used to living in this world where I'm talking about these things that seem kind of abstract. You know,  it's very dry knowledge management  systems, like, come on, like nobody's  interested in this. But people I, you know, they really understood they really  wanted this. They needed  this resource. And so they bought in and they supported it, and they put their information in it. And they started using the search tool. And it was kind of glorious.

Jeff Frick:
That's great. So, one of the  things that that Darren used to  always talk about, one of my favorite lines  of his was that all remote  forces companies to be good at things that all companies should be good at. And knowledge sharing  and the lack of the ability just to tap somebody  on the shoulder to get the answer to a question is, is one of the great examples. And you talked about  in your talk really digital first. And really it's another way to  kind of think of that being digital first. Now with AI and  the acceleration of AI, it makes a big difference in your position to go forward. If you are already maybe digital centric, maybe you're not  quite digital first, but talk a little bit about how digital first is such  an important component to being successful in this next couple of years is because of this is crazy AI thing.

JJ Reeder
Well, this is why I think  that remote first companies as a group are going to be  leading actually in the next wave of AI adoption because remote  first companies didn't just embrace remote work or in order to embrace  remote work, they had to also embrace digital communication, digital collaboration, digital connection. And they wrote  everything down, and they figured out systems to transfer information and get it flowing throughout the company. And that is something that I think a lot of companies are still really  catching up on, which is a lot of what I talked about in my talk just now. I think that remote first companies have this massive potential to really have a head start on AI implementation, and what I think we're going  to start to see that come to fruition really quickly  as these companies, certain ones, start to  just leave the pack.

Jeff Frick:
So another great line Brian Elliott likes to use from formerly  Future Forum Now doing his  own thing is, is that the  same management philosophies,  practices, attitude that enable people  to successfully implement distributed work,  hybrid work, remote work are the same things  that enable people to enable  AI adoption. And we know  right now one of the big enterprise challenges is AI adoption. Everyone knows they want to use it, they're trying to use it. But it's really interesting I thought that Brian pointed out because it's about agency, it's about risk taking. It's about getting  outside the box, and it's actually the same  behaviors that are going to support, AI utilization AI,  you know, trial.

JJ Reeder
Absolutely. That's absolutely right. And it's more than that. It's not just  about risk taking. That's a very  important part of it. It's not just about thinking  outside the box, though. It's being willing to do  the hard, dry work that actually supports the execution. So you can have the big idea. But unless you do, what it takes to actually execute  on that idea it’s just  an idea. And I think that some of these companies really understand it is hard to run a  company remotely. It is  not easy. And so I think that some of these companies have already built the muscle that they need  to sustain the effort to really move ahead in the AI adoption phase.

Jeff Frick:
Do you think the  change in attitude is just because of the reaction of something like a ChatGPT to know that now  I can actually like I can have a conversation with a computer and extract  information that way versus kind of  old school queries. And the  complexity of trying to get  information is that change  the acceptance or excitement or willingness to invest in the senior team into finally the the dream of  knowledge management that we've had forever and ever.

JJ Reeder:
You know what? I think that's  so much a part of it. I think you're absolutely right on about that. And I actually had never  really heard it put that way. So thank you  for bringing that up. Yeah,  I do they It is  transformative, even for me to be able to have a conversation [Jeff] Right with ChatGPT And like have  a discussion and share ideas  and get feedback. And I think throughout the industry and  throughout many industries, I think executives are really leaning into AI, which means that  they're trying stuff. They are conversing with ChatGPT, and once they start to reach that level where they're having that transformative experience I think absolutely it starts to make sense. It starts to click. You start to see, okay, this is what I can do. But I also think that it's really easy for us to just accept  what an AI tells us such as  ChatGPT and to not really  be super concerned about the quality of  the answer that it's giving us. And there's a risk to not having good information underlying that answer. So it's a  yes and no thing.  I think that yes, it drives adoption, but I'm still concerned about that rigor that we actually need to have good knowledge inside of an organization.

Jeff Frick:
Right. Because there's the rigor,  as you said before, garbage in,  garbage out. And then there's the rigor in terms of the  appropriateness of the  return answer. I had a great  interview with a guy, Charles Corley works for  a company called M Moser and  Associates, and their  attitude is treat everything that  comes back from ChatGPT as a junior  colleague. A really smart junior colleague, a really fast junior colleague, one that never complains or takes time off. But you know, but I was like Charles, what about hallucinations? And he’s like, you have  to check the work. So use it, as you said,  as a thought partner. But at the  end of the day, before you sign on the dotted line, you got to  check the work.

JJ Reeder:
Absolutely. And I'm so concerned that that's not necessarily happening because it just feels  so organic. You really feel like you can trust this answer. And I think that's another muscle that we now have to build.

Jeff Frick:
Yeah, it's really tricky if it's  in an area that you don't know because if it's an area that you know not only can you  see the hallucinations, but more importantly, you know the  value of the hallucination is it material  or immaterial. But if  it's something you have no clue about and you just  take it as gospel, you know, you can really  get yourself in big trouble.

JJ Reeder:
That’s true.

Jeff Frick:
Okay, so  last question. One of the  hardest things and it wasn't directly in your talk is driving engagement with distributed teams, remote teams how should people think about, approach engagement. Because we know engagement retention is so so important. What's this. What's some of the secrets to keeping good engagement with remote teams?

JJ Reeder:
You know what I'm actually going to talk about this tomorrow.

Jeff Frick:
Oh, good. A little preview for all the local folks.

JJ Reeder:
It’s part of a  session tomorrow It's going to be about engagement

Jeff Frick:
Dang, I didn't study  my notes on that.

JJ Reeder
It’s like a lightning round  of two minute talks. With a whole bunch of people.

Jeff Frick
Okay Um so. Well, you could take more  than two minutes here. So go ahead

JJ Reeder:
So my quick  spiel on it is that  we for the past several years and maybe for  a while now have been thinking about  culture and engagement as something  that is layered on top of the work that we do, right? So we think you go  do your work, and then you go to an all hands or you go to a retreat and you connect  with your team. But the reality is that's like less than 1% of  the time that we spend at work. And actually we are  collaborating with people in every moment that we work and If you don't think  that's building culture, then you  are wrong. So I think we need to  really start thinking about building engagement and  culture in the day to day work. For me, what that means  is making work easy. If we have  good systems that empower people to  be effective at their work, then they start  to enjoy their work and they start to enjoy the people that they work with because they're  relaxed, they're showing up  as more confident. They feel more possession of their results. And they start to really believe that it's possible to have a good  work experience to do  their work. They start  to feel proud and pretty soon this is  producing engagement.

Jeff Frick:
Love it. Well, JJ, it was so great to finally meet you in person. We've been LinkedIn buddies  for a long, long time long time  it’s great to meet you.

JJ Reeder:
Absolutely

Jeff Frick:
And thank you for the insight. Really,  useful stuff. And finally, you know,  is finally the dream of a unified knowledge management system in the organization Is finally almost here  it sounds like

JJ Reeder:
I love it,  I love it. Yeah. There's so much potential. Thank you so much.

Jeff Frick:
Thank you. All right. She's Jessica. Excuse me. She's JJ,  I'm Jeff, you're watching  Work 20XX on the road from Running Remote in Austin, Texas. Thanks for watching. Thanks for listening on the podcast. Catch you next time. Take care.

Cold Close:
We're out.
Thank you.
How fun Yeah.

“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX podcast with Jeff Frick Ep40 from Running Remote

‍© Copyright 2025 Menlo Creek Media, LLC, All Rights Reserved

“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX podcast with Jeff Frick, Ep40  

“JJ” Jessica Reeder 

Director, Remote Organizational Effectiveness, Upwork 

LinkedIn 
https://www.linkedin.com/in/jessicareeder/

JJ Reeder dot com
https://jjreeder.com/

Bluesky 
https://bsky.app/profile/jjs.business

—--

Upwork Research Institute 
https://www.upwork.com/blog/introducing-research-institute

—----

Select appearances


2025-Apr-29
“Handbooks on Steroids: In the Age of AI, Knowledge Management is a Make-or-Break Strategy”
Running Remote Conference Session
https://runningremote.com/ai-handbooks-and-the-future-of-remote-work-written-interview-with-upworks-jj-reeder/

2024-Jun-04
“Cultivating Culture in Distributed Teams with JJ and Charlotte”
Epoch Podcast
https://podcasters.spotify.com/pod/show/epochapp/episodes/Cultivating-Culture-in-Distributed-Teams-with-JJ-and-Charlotte-e2c97vuSpotify for Creators+1Spotify for Creators+1

2023-Sept-28
#171: To Make Remote Work Effective Requires Thinking About Others: Jessica "JJ" Reeder of Upwork
Wise Decision Maker YouTube Channel
https://www.youtube.com/watch?v=CKZSEVgcJ3s&ab_channel=WiseDecisionMaker

2023-Jul-25
“Inspired People, Inspired Places”
Orion Growth YouTube Channel
https://www.youtube.com/live/dk_O9jLvjhY?si=0BUbXg0tf8KRCScyLinkedIn+2Turn The Lens Podcast+2LinkedIn+2

—-------------------------

Other items mentioned in the interview 

----------------------------

GitLab’s Guide to All-Remote
https://handbook.gitlab.com/handbook/company/culture/all-remote/guide/

Atlassian State of Teams 
https://www.atlassian.com/blog/state-of-teams-2025  

Panopto Valuing Workplace Knowledge 
https://www.panopto.com/resource/valuing-workplace-knowledge/

2025-April-18
Charles Corley: Culture, Wellness, Visualization, AI Colleague | Work 20XX Ep34 
https://www.work20xx.com/episode/charles-corley-culture-wellness-visualization-ai-colleague-work-20xx-ep34
https://www.youtube.com/watch?v=LkNGFqywW7g&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt 
https://open.spotify.com/episode/30aXprLp2ccy966Ut3fxbC?si=ztzCBiR_Rh2M7YJEt9rbow

2024-Aug-13
Brian Elliott v2: AI, Experiment, Outcomes, Trust | Work 20XX Podcast with Jeff Frick Ep28
https://www.work20xx.com/episode/brian-elliott-v2-ai-experiment-outcomes-trust-work-20xx-ep28
https://www.youtube.com/watch?v=Iv6SwrHUmJo&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
https://open.spotify.com/episode/53knlL5u3R5DNOfMCMMwlI?si=PD9FIeBhSfKBC-jsnYolhQ

2023-June-23
Brian Elliott: Connected, Effective, Workplace Future | Work 20XX Podcast with Jeff Frick, Ep15  
https://www.work20xx.com/episode/brian-elliott-connected-effective-workplace-future-work-20xx-15 
https://www.youtube.com/watch?v=rKiBzaLJ57o&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
https://open.spotify.com/episode/77vADFHykJG60PgAVn5RRF?si=FGWUr_7jQlCMwNy1S1vEyw

2021-Dec-22

Darren Murph: Remote-First, Asynch Communications, Operating Manual | Work 20XX #01 
https://www.work20xx.com/episode/episode-1-darren-murph
https://www.youtube.com/watch?v=2A8J6QTqZaU&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
https://open.spotify.com/episode/7JksH1BNyNHTjzU6Ihvyje?si=cGZuoRDeSSOZNC1W1BsJCA

2020-May-01
All-remote GitLab offers advice and resources for life away from offices
By Mark Albertson, SiliconANGLE Media
https://siliconangle.com/2020/05/01/all-remote-gitlab-offers-advice-and-resources-as-companies-adjust-to-life-away-from-offices-cubeconversations/

2020-Apr-29
Darren Murph, GitLab | CUBE Conversation, April 2020 
SiliconANGLEtheCUBE YouTube Channel 
https://www.youtube.com/watch?v=SP7u0gYCHiY&ab_channel=SiliconANGLEtheCUBE

2018-July-16
Inefficient Knowledge Sharing Costs Large Businesses $47 Million Per Year
Panopto Release 
https://www.panopto.com/company/news/inefficient-knowledge-sharing-costs-large-businesses-47-million-per-year/
https://www.panopto.com/resource/valuing-workplace-knowledge/

—-------------------------

Thank you Liam, Egor, and Ana and the entire Running Remote team for the collaboration. Running Remote and Work 20XX, goes together like peanut butter and chocolate. 

Running Remote
https://runningremote.com/

—------------------------

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‍© Copyright 2025 Menlo Creek Media, LLC, All Rights Reserved 

Jeff Frick
Founder and Principal,
Menlo Creek Media

Jeff Frick has helped literally tens of thousands of executives share their stories. In his latest show, Work 20XX, Jeff is sharpening the focus on the future of work, and all that it entails.