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 every few weeks, not every few years.

We cover:

• Zapier's AI fluency rubric — one of the first of its kind, open-sourced to the community, and rebuilt from scratch as the bar for "capable" has kept moving

• Why raising the bar meant Zapier also had to raise the level of support, building resources for candidates to close the gap rather than just screening them out

• Ezra, the voice AI Zapier uses for first-round interviews — and the surprising discovery that candidates and recruiters both prefer it to a human screen

• Why an AI interviewer that doesn't interrupt, doesn't show impatience, and never runs out of time zone turns out to be the more humane first conversation, not the less

Everything else is noise. Applications are noise. What's left, once you strip that away, is whether someone is actually climbing — and whether the people evaluating them can see it happen in real time.

Better hiring isn't about finding people who already know everything. It's about finding people on the way up. Tracy makes the case.

Recorded live at Running Remote 2026, Austin, Texas.

Guest: Tracy St.Dic, Global Head of Talent, Zapier | zapier.com | linkedin.com/in/tracy-stdic

Work 20XX explores the future of work, distributed teams, and human performance in the age of AI. Hosted by Jeff Frick.

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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 she was scared of AI at first. She never worked at a tech company, never learned to code, and did not see herself as a technical person. That changed when she took a Lead with AI certification program and realized the skills translated more directly than she expected. Now she has built her own custom GPT trained on the five-piece meeting framework she teaches clients, purpose, product, process, pre-work, and people, and uses it to prep every agenda she runs.

The conversation also digs into her sharpest observation of the day: AI adoption inside a company follows the same spectrum she has spent 15 years mapping for remote and hybrid work. Some organizations are virtual-first and moving fast, some are still figuring out basic policy on which LLMs employees are even allowed to use, and Sacha works both ends of that spectrum at once, from the executive suite down to the team actually trying to get the tools to stick.

Her advice for anyone intimidated by the mandate from on high to "go use AI": experiment in your personal life first. She has used LLMs for her own family scheduling. Once it clicks personally, bringing it to your team gets a lot easier.

We also cover her fifteen-year remote-iversary, the ERG she helped build at Clorox that grew faster than any other in the company, and her hot take on scheduled send.

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 one actually means in practice, from a weekly all hands where finance shares real revenue numbers, to an explicit team-wide push to assume positive intent before reacting to a Slack message. She also talks through the recent integration of We Are For Good, a nonprofit media and community company Givebutter acquired, and why culture fit was the very first thing she checked.

The conversation closes on AI adoption inside a remote-first team, and Lucy draws a direct line between the skills that make distributed work succeed and the skills that make AI adoption succeed. Her advice for managers right now: PR for your team. When someone on your team is doing something sophisticated with a new tool, make sure it gets seen.

Oh, and yes, we talk about Mr. Butter, the company mascot with a butter slice for a head.

Lucy Stein: Clear is Kind, Assume Positive Intent | Work 20XX with Jeff Frick Ep 64 from Running Remote

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 own workforce analytics tool built to track productivity and in the act of usage behaviour, converts it from what might be percived to be a survealance too, into a trust-building platform.

Vini also makes the case that a company is a sports team, not a family, and explains why that distinction matters for how people actually commit to their work. We talk through what career growth looks like when the org chart is flat and vertical promotion is not a given, and Vini's answer is lateral growth: more responsibility, more influence, more relevance, even without a new title attached.

The most surprising thread runs back to his time as a sommelier in a 2-Michelin-star restaurant. Hospitality taught him that the job was never the paperwork. It was the people. That is the whole philosophy, transplanted into HR at scale.

Vinícius Coelho: Know the Team, Growth and Impact | Work 20XX with Jeff Frick Ep63 from Running Remote

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 growth opportunity, and the companies that treat it like one will leave the others behind. The conversation starts with what it actually feels like at the top of the org chart, where there's no support built into the structure, and moves through the operational practices Nick built at Help Scout to keep a remote team calibrated, honest, and moving in the same direction.

We cover:

• The loneliness of the CEO role and the two things that were transformational: a coach who could give hard criticism without organizational risk, and a peer group built on shared values
• The "War Council," a technique Nick picked up from Wade Foster at Zapier, using AI personas to pressure-test decisions from multiple angles when nobody around you wants to deliver bad news
• Calibration as an operating practice, not a document. Managers getting together every six months to stress-test rubrics, align on what great looks like, and minimize bias across the organization
• Why hard conversations don't happen in remote companies unless they're baked into the operating system
• Bifurcating engagement data to focus on high-performer feedback, and why that's not leaving anyone behind, it's investing where the ROI is highest
• High agency as the unlock for the AI era. Nick's belief that the capacity is in everyone, though in some folks it might just be dormant. You've got to wake it up.
• Why leaders thinking about AI only in terms of cutting costs and improving productivity are taking a short-sighted view. You can't save your way to growth.

The job is still the job. The tasks are going to change radically. For an entrepreneur, this is heaven.

Recorded live at Running Remote 2026, Austin, Texas.

Guest: Nick Francis, Co-founder & Chairman, Help Scout | nickfranc.is | helpscout.com

Work 20XX explores the future of work, distributed teams, and human performance in the age of AI. Hosted by Jeff Frick.

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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 a behavior change problem — and why most companies are treating it like a software rollout
• The thoughts-feelings-behavior chain that drives every business outcome anyone actually cares about
• The impossible squeeze on middle managers right now, asked to hold teams together while navigating their own uncertainty
• The bifurcation Bobbi sees coming: companies that double down on people plus the tool, versus companies using AI as cover to cut

When people are stressed and uncertain, their amygdalas are getting beat up all day long. A stressed, defensive amygdala is not a connecting brain. It's a surviving brain. And that shows up directly on the bottom line.

Good psychology is good business. Bobbi makes the case.

Recorded live at Running Remote 2026, Austin, Texas.

Guest: Bobbi Wegner, Founder & CEO, Groops | drbobbiwegner.com | joingroops.com

Work 20XX explores the future of work, distributed teams, and human performance in the age of AI. Hosted by Jeff Frick.

Transcript and Show notes - Click Here

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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 experience shaped everything, how she hires, how she leads, how she thinks about who gets a seat at the table and whether the table itself is worth sitting at. Being humans first and employees second isn't a tagline for her. It's a worldview forged long before she had a title.

So we got into the good stuff. Starting with the waiter test. For critical hires, Gianna takes candidates to dinner and watches how they treat the wait staff. Not as a trick. As a window. One CRO finalist interviewed brilliantly right up until the server got his order wrong. That was the end of the process. It's a small moment. It tells you everything.

We talked about mistake-making as a leadership competency, normalizing failure fast, cost-effectively, and without fear, and why organizations that run on cultures of fear are leaving performance on the table every single day. We talked about the machine-to-machine hiring pipeline and what gets lost when the humans step out of the loop. And we went to the hard places: DEI, the political headwinds, the companies pulling back. Gianna's answer was clear and unequivocal. Call it whatever you want. If the words are triggering, find new words. But the spirit, building inclusive, diverse teams because the science says they produce better outcomes and because it's the right thing to do, that doesn't get to go away because it became inconvenient.

And she made a prediction, on the record: companies using AI as cover for layoffs are going to see a boomerang. They've over-cut. They'll need to rehire. And the talent they let go won't be waiting.

Good leadership is good leadership. These aren't lessons for remote teams or hybrid teams or any particular org chart configuration. They're for anyone who takes people seriously enough to be intentional about the conditions they create.

Please join me in welcoming Gianna Driver to the Work 20XX Podcast.

---

*Editor's Note: Recorded May 2026 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and the entire Running Remote team.*

*Gianna Driver: How'd You Treat the Waiter, Humans First Employees Second | Work 20XX Ep60 with Jeff Frick from Running Remote 2026*

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*Transcript and Show Notes – Click Here*

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 decade ago, working alongside Darren Murph at GitLab in those early days, helping define what would become the blueprint, reference, dictionary, thesaurus and operations manual, the anchor document, for distributed work around the world, the 'GitLab Remote Work handbook, ' published open source, for the benefit of all. That kind of longitudinal perspective is rare, and she's added to it since, moving from GitLab through other fully remote companies to her current role as Head of People at Doist, 100% remote, 100+ people, 40+ countries.

So we got into the good stuff. Extreme async, functioning radical candor against 40+ cultures, and self managed careers. What does it take to create the conditions where honesty lands as a gift instead of a grenade, across so many different baseline cultural norms? Nadia explained their shadow program, giving people a chance to try before they buy in different types of roles, departments, and functions. And showing her care for the people, Nadia reinforced that even if that if helping someone grow means they eventually outgrow the company, that's not a failure. She celebrates the growth and development. That's the whole point. It gets celebrated. A great illustration and example of the mature, adult, professional, working demeanor required to operate in a world that prioritizes growth and improvement, at the risk of ruffling a few feathers (unintentionally).

And of course we got into how Nadia specifically and Doist generally are leveraging AI to deliver more with their existing team.

Good management is good management. These practices aren't just for remote or hybrid teams. They're for any leader who takes people seriously.

And if Nadia was willing to fly half way around the word to share, I can assure you it well worth your 25 minutes.

Please join me in welcoming Nadia Vatalidis to the Work 20XX Podcast.

Editor's Note: Recorded May 2026 at the Running Remote conference in Austin, Texas. Special thanks to Liam, Egor, Ana, and the entire Running Remote team.

Nadia Vatalidis: Extreme Async, Unguarded Feedback, Career by Initiative | Work 20XX Ep59 with Jeff Frick from Running Remote 2026

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