“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work 20XX Ep40
Release Date: 05/09/2025
Work 20XX with Jeff Frick
Tracy St.Dic is Global Head of Talent at Zapier, where she's spent the last several years rebuilding hiring from the ground up for an AI-native world. "Slope, not snapshot" is her phrase — she's not interested in where a candidate stands today, she's interested in the angle of their learning curve. In this episode, Tracy makes the case that most of what companies call signal in hiring is actually noise. Resumes have flattened into interchangeable copy. Applications are increasingly fraudulent. And the traditional recruiter screen wasn't built for a world where the tools themselves change...
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Sacha Connor has been coming to Running Remote since 2019, when the conference was held in Bali, and this episode marks her third appearance on Work 20XX. Please join me in welcoming Sacha Connor back to the Work 20XX podcast. In Austin for the second year running with the team at Running Remote, we sat down with Sacha, founder and CEO of Virtual Work Insider, to trace how the conversation at this conference has evolved since that first trip to Bali, from synchronous versus asynchronous communication debates to what's dominating the room now: AI adoption inside distributed teams. Sacha admits...
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Lucy Stein just watched Givebutter cross $10 billion in donations raised for nonprofits, ten years after she joined the company as employee number seven. Please join me in welcoming Lucy Stein to the Work 20XX podcast. In Austin for the second year collaborating with the team at Running Remote, we sat down with Lucy to learn how she built a People function from a completely blank slate, and what it takes to keep it intact as the company scales past 200 employees. Givebutter's culture runs on three codified values: radical transparency, no assholes, and wired for fun. Lucy breaks down what each...
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Vinícius Coelho: Know the Team, Growth and Impact | Work 20XX with Jeff Frick Ep63 from Running Remote Vini Coelho recently added Chief of Staff and VP Operations to his People and Culture role at Time Doctor, 140 people spread across 40 countries and 24 time zones. And Vini's met them all. Please join me in welcoming Vini Coelho to the Work 20XX podcast. In Austin for the second year collaborating with the team at Running Remote, we sat down with Vini to learn how he does creates and manages culture across such a wide georgraphical and cultural spread. Time Doctor uses its...
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Let me re-read the transcript to nail the details and get Nick's language right.Here's the Libsyn description, built to match the Bobbi Wegner template: Nick Francis: Calibration, War Council, High Agency Investment | Work 20XX Ep 62 Nick Francis co-founded Help Scout in 2011 and ran it as CEO for 15 years before stepping into the Chairman role in late 2025. Today he coaches founders, facilitates a CEO peer group, and speaks on leadership, remote culture, and building companies for the long haul. In this episode, Nick makes the case that the AI moment is not a cost-cutting exercise. It's a...
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Bobbi Wegner: Culture Is Relationship at Scale | Work 20XX Ep 61 Bobbi Wegner is a clinical psychologist, Harvard lecturer, and Founder and CEO of Groops — a psychology-based coaching platform built on a simple, solid premise: people are social beings, hardwired for connection. "Animals in suits" was her phrase. In this episode, Bobbi makes the case that culture is relationship at scale. Not the posters on the wall. Not the values deck. The actual strength of the connections between the people doing the work, accumulated one interaction at a time. We cover: Why AI adoption is fundamentally...
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Gianna Driver didn't come to Running Remote 2026 as a remote work evangelist. She came as a Chief People Officer who believes, deeply, that how you design the spaces where people gather, physically, culturally, organizationally, determines everything about the kind of company you actually become. Not the kind you say you are. The kind you are. And that conviction didn't come from a business school case study. It came from growing up on the other side of privilege. Her mother emigrated to the US as a mail-order bride. Gianna knows what it feels like to be on the outside looking in. That...
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Nadia Vatalidis flew 10,000 miles, almost halfway around the world, to share her insights at Running Remote 2026 in Austin. And the distance is more than geographic. She doesn't live in the US, Europe or Asia. Her vantage is from South Africa, which povides a unique look 'back' if you will at the rest of the tech scene, with a differernt 'reality' check than I have here in Palo Alto, CA, in the eye of the storm, or even Asia or Europe or Austraila for that matter. Sometimes it's harder to tell what's happening when you're standing in the middle of it. Nadia was there at the beginning. Over a...
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Liam Martin joined me fresh off the stage at Running Remote's 10th event, a milestone that puts into sharp relief just how much the landscape has shifted since that scrappy little secret called remote work became the world's crash course in 2020. What started as documentation, async, and trust has evolved into something far bigger: the realization that the skills and culture remote-first organizations built out of necessity are now the precise prerequisites for becoming AI-native. The conversation moved fast, from the absurdity of AI writing reports that humans then feed back into AI to...
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Indiana went 16-0 and won the national championship with 7 blue-chip recruits. Their opponents had 110+. What does Curt Cignetti's talent evaluation strategy teach us about the future of work? It's not about return to office. It's not about hybrid schedules. It's about creating an environment that enables people to do the best work of their lives—finding the best talent, empowering them with AI and modern tools, and building a culture where everybody plays every play. This is the future of work: strategic evaluation over pedigree, development over credentials, empowerment over control....
info_outlineJessica “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.
“JJ” Jessica Reeder: Scaling Knowledge, Evolution, Operations | Work podcast with Jeff Frick 20XX Ep40 from Running Remote
YouTube - Click Here
https://www.youtube.com/watch?v=WmpI_FOdyyo&list=PLZURvMqWbYjmmJlwGj0L0jWbWdCej1Jlt
Transcript and Show Notes - Click Here