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HR As The Culture Keeper with Jamie Jackson of HR Besties
Estimated reading time: 7 minutes
In this special guest episode of Wellable Weekly, Geoff sits down with Jamie Jackson, co-host of the number one HR podcast, HR Besties, and founder of Humorous Misery Media, the meme page she created during the darkest days of COVID to find some levity in one of the most stressful periods HR professionals have ever navigated. Jamie brings 23 years of HR experience, a sharp sense of humor, and a keen perspective on why HR keeps getting blamed for decisions it didn’t make, what the erosion of benefits says about employer priorities, and how to handle a politically charged workplace environment. The episode closes with a conversation about the four-day work week and why Jamie and Geoff think it is more achievable than most people realize.
Short on time? Here are the key takeaways:
- HR’s reputation takes a hit when organizations use it as the messenger for decisions that were made by the C-suite, and the gap between what HR recommends and what leadership decides often goes unseen by employees
- The best companies Jamie has worked for are ones where HR has a genuine seat at the table and leadership actually listens—those organizations build measurably stronger cultures as a result
- Benefit erosion—including 401k match suspensions, shrinking health coverage, and elimination of EAPs — is accelerating in the current labor market, and companies cutting now may be making a long-term brand mistake they’ll feel when the talent market shifts
- Navigating politics in the workplace requires proactive, clearly communicated policies rather than reactive ones, especially as social media increasingly blurs the line between personal and professional identity
- The four-day work week is more achievable than most people believe, with international pilots consistently showing equal or higher productivity — and AI-driven efficiency gains may finally make it a realistic conversation in the US
Episode Summary
Why HR Gets the Blame It Doesn’t Always Deserve
Jamie Jackson did not plan a career in HR. She stumbled into it as a college student at the University of Tennessee, helping out a manager who moved to an HR role at Sears and invited her along. What she discovered was a genuine love of helping people, whether it was explaining a paycheck, navigating a benefits question, or being the person in the room who understood what employees actually needed. Twenty-three years later, that core motivation has never changed.
Jamie is candid about the villainization of human resources: HR professionals are often the face of decisions they did not make and sometimes actively fought against. Her own example is a PTO rollover policy she battled to preserve at one employer. She lost, but then had to stand in front of employees and deliver the news. From the outside, HR looks like the bad guy. From the inside, HR was the only one in the room arguing for the other side.
Geoff connects this to recent headlines, including Uber cutting a quarter of its HR team and the Bolt story where dissolving HR became a public relations moment. Jamie’s reaction to Uber is pointed: Uber built its employer brand around culture for years, using it as a recruitment advantage. Cutting the function responsible for maintaining that culture is a gamble with long-term consequences that may not show up immediately but will compound over time.
Her broader argument is that HR’s influence is real but frequently misunderstood. The best organizations she has worked for are the ones where HR has an actual seat at the table, can surface employee concerns directly to leadership, and is trusted to say when a decision is going to land poorly. Those companies have better cultures, not because HR has all the power but because leadership listens to the function that is closest to the workforce.
Benefits Are Eroding, and Employees Are Stuck
The conversation about benefit rollbacks is one Jamie finds deeply frustrating, partly because she has lived it from both sides. The current pattern, companies suspending 401k matches, passing healthcare premium increases directly to employees, quietly eliminating EAPs, reflects a labor market dynamic where employers have regained leverage and are using it to cut costs. Employees who would normally vote with their feet are staying put because the job market is volatile and the risk of leaving feels too high.
Jamie’s concern is not just the immediate financial impact on employees. It is the long-term reputational cost to employers who make these cuts when they do not have to. When the labor market shifts again, employees will remember who protected their benefits and who did not. The companies that held the line will have a genuine recruitment advantage. The ones that treated benefits as a lever to pull in a favorable market will have a harder conversation to have with candidates who have options again.
Politics, Social Media, and the Fine Line HR Has to Walk
The politically charged environment of the past several years has made one of HR’s oldest challenges significantly harder. Jamie’s position is nuanced: she does not believe banning all political conversation is realistic or even desirable. Healthy debate is part of a functioning workplace, and employees are adults who are capable of disagreeing without HR intervention. But there is a line, and physical expressions of political identity in shared workspaces, things that a colleague might find offensive or exclusionary, are where HR needs a clear, proactive policy rather than a reactive one.
The social media dimension has added an entirely new layer of complexity. Employees are representing their employer’s brand on personal platforms around the clock, often without realizing the policy implications. Geoff notes that many companies now explicitly address how employees should handle their employer affiliation on social media, but the communication of those policies is frequently inadequate. People are not thinking about their social media policy on a Saturday afternoon. The employer’s responsibility is to make sure they know what the rules are before it becomes an incident.
Jamie shares several examples from her own experience, including anonymous tips about employee social media activity and the growing pattern of public videos being sent to employers to trigger termination.
Summer Fridays, Four-Day Work Weeks, and What Companies Still Get Right
Not everything in the conversation is about what is going wrong. When Geoff asks Jamie where she has seen companies genuinely getting it right, she turns the question back to Wellable, noting that she spotted summer Fridays in an email exchange before the recording and that she had not seen a company offer that policy since around 2014 or 2015. It is a small thing, but Jamie’s point is that small things add up. A policy that says, we trust you, we want you to enjoy your summer, go enjoy your Friday afternoon, sends a message about company values that a press release about culture never could.
The conversation extends to the four-day work week, a subject Geoff describes as a personal obsession. International pilot programs have repeatedly shown that moving to a four-day schedule does not reduce output and in many cases improves it. Jamie is enthusiastically in favor, noting that she could comfortably complete a full week’s work in four days. Geoff’s argument is that AI-driven efficiency gains may finally make the four-day work week politically achievable in the US, since the productivity conversation is shifting from how many hours people work to what they actually produce in those hours.
Frequently Asked Questions
Jamie Jackson’s explanation is that HR is frequently the function tasked with communicating decisions that leadership made, sometimes over HR’s explicit objections. When a benefit gets cut, a policy changes, or a termination happens, HR is often the visible face of that moment even if it spent considerable effort trying to prevent it.
Jamie’s advice is to keep fighting and frame every people-related decision as a business decision. Benefits, culture, and retention are recruitment tools. The argument that holding the line on benefits or policies will pay off when the labor market shifts is a business case, not just an ethical one.
Employee assistance programs are among the least expensive benefits an employer can offer. When they are properly communicated and promoted, they provide genuine value to employees navigating mental health, financial stress, legal questions, and family challenges. Cutting an EAP to save money is, in Jamie’s view, a signal that leadership does not fully understand what the benefit is doing for the workforce.
Jamie’s position is that healthy, respectful political discourse should not be banned outright, since that approach tends to be both unenforceable and counterproductive. What companies should do is have clear, proactive policies about physical expressions of political identity in shared spaces and about how employees represent the company on social media.
Social media means employees are representing their employer’s brand around the clock, often without thinking about it. HR is increasingly fielding anonymous tips, reports of employee social media activity, and requests to act on content posted on personal accounts. Jamie’s advice to employees is to be careful, because the line between personal and professional reputation has never been thinner.
Geoff and Jamie both think it is more achievable than most people believe. International pilots have consistently shown that four-day schedules maintain or improve productivity. The argument that AI-driven efficiency gains will make the four-day work week more politically viable in the US is compelling: if the tools exist to produce the same output in less time, the question of whether a five-day schedule is actually necessary becomes harder to dismiss.
Full Episode Transcript
Geoff: Welcome to the Wellable Weekly Podcast, where we talk about key topics and trends at the intersection of well-being, technology, and HR. I’m Geoff. I’d like to welcome a very special guest to the podcast this week, Jamie Jackson. In addition to being the self-proclaimed Chief Meme Officer, Jamie is one of the hosts for the HR Besties podcast. She’s the founder of Humorous Resources. And she has an impressive background in a number of different HR leadership roles, including posts at Tractor Supply, Marriott, and CareSpot. Jamie, welcome to the podcast.
Jamie: Thanks for having me.
Geoff: Chief Meme Officer — an incredible title, a different take on the traditional CMO role. Tell me a little bit about your background and how you got to where you are today.
Jamie: Yeah, so I kind of fell into HR. I think a lot of HR professionals fall into it. We don’t dream when we are younglings, “I want to be an HR professional where everyone hates me.” I fell into it in college. I was actually working at Sears — rest in peace — in the jewelry department. My boss was promoted to HR manager and she said, “Hey, would you want to come back and be my HR assistant?” And I was like, what are the hours? Because I’m in college, I went to the University of Tennessee, football was a big deal, and I wanted to know if this was going to get me out at better hours.
So yes, I went back there, and I actually really enjoyed it. I enjoyed helping people. It could be something simple, like helping them understand their benefits or their paycheck. There were a lot of college students there, so even I was learning things I didn’t understand. I was just a business major at the time, and my major turned into human resource development. That’s just kind of where I’ve landed for the last 23 years.
In 2020, I found myself working for a nonprofit clinic with four locations as the HR director and a department of one. It was scary. I felt underqualified with all this responsibility to take care of not only our employees but our patients, and everyone they touched, because COVID was scary and we didn’t really know much about it. I felt very alone.
That’s when I created my meme page, Humorous Resources, in September of 2020. I just started creating memes. I didn’t have any goal for it to become anything. It was just a way for me to be silly and goofy. I figured there had to be other people like me out there going, “What the heck are we supposed to do right now?” Every day I was checking the CDC website because things were literally changing overnight. But I had Humorous Resources to take the edge off, and it exploded.
Then in July of 2021, I created Millennial Misery because I’m an elder millennial with a lot of nostalgic memories. That’s when I coined Chief Meme Officer, because I was making all these memes and had all these pages. I was still hiding — not showing my face because I was still a professional. Now I also have a parenting meme page and my own personal page.
Geoff: What started as a creative outlet during a challenging time turned into something that resonated with a lot of people. That fundamental desire to help people in a business setting seems to be the tie that binds a lot of HR professionals. Yet there’s this element of being perceived as the villain. You’ve got CEOs like Ryan Breslow at Bolt claiming he got rid of HR when he really just renamed the team. And then you have legitimate cuts like Uber just cutting a quarter of their HR team. What’s your take on why HR gets blamed for everything when so many people in the function have genuinely good intentions?
Jamie: Well, I think there are bad HR people — but there’s bad everyone. There are bad CEOs, bad accountants. I think HR gets villainized because we’re often the people communicating poor decisions from leadership. It doesn’t mean we haven’t pushed back or voiced our concerns, but it doesn’t mean that leadership is listening to us or even cares what we have to say.
I try to say on social media: I’m also an employee. These policies affect me too. I remember at one company they were changing the PTO rollover policy to only 40 hours. I fought tooth and nail to keep the old policy. I fought and I fought and I fought as hard as I could, but ultimately I lost. And then I’m unfortunately the one in the town hall saying, effective such and such date, you will only be able to roll over 40 hours. You look like the villain because you’re communicating these things. Or you’re the one processing the termination, having the difficult conversation, while the manager sits there but isn’t doing the talking.
A lot of times people don’t actually understand what HR does or the role HR plays. That’s why I’ve tried very hard on social media to shine a light on what HR actually is. There’s this weird misconception that we hold so much power when we don’t. The best companies I’ve ever worked for are the ones where HR actually has a seat at the table, we’re allowed to be vocal, and I’m able to say to my boss candidly, “Hey, I just had a conversation with someone and I’m bubbling this up because I’m also concerned.” Those are the companies with the best culture.
When I see Uber slashing half their HR department, I think: Uber bragged for years about their culture. That was a huge hiring tactic for them. How are they going to maintain that culture if they don’t have someone there to constantly maintain it? That’s a huge piece of HR that I don’t think people actually realize.
Geoff: You’ve said before that HR has very little power but wields a lot of influence. And that example perfectly reflects that. Now we’re seeing companies in the news pulling back on 401k matches, shrinking health benefits. Are you hearing that from your community as well, and what do you feel HR pros should be fighting for right now?
Jamie: Absolutely. It’s been insanely disappointing. I’ve read about companies stopping 401k matches. Some are completely rolling back benefits they offer. Healthcare has been increasingly worse over the years, and those increases have impacted both companies and employees. A lot of companies are just passing a 25% increase straight to employees.
It’s been such a weird shift to watch. Employees feel stuck because the job market is volatile and there are high unemployment rates. So they’re unfortunately having to deal with insanely high health premiums or losing their 401k match. Even something that might seem small, like eliminating an EAP — a lot of companies don’t even realize the EAP is typically one of the cheapest things you can offer, but it’s incredibly valuable when HR knows how to properly promote it.
For HR professionals, I don’t know if there’s much we can do but to keep fighting and try our best to keep fighting for those resources for our employees. And how you make that case is to frame it as a recruiting tool. When we get over this hump of the current job market, it’s still going to be a recruiting tactic. Employees will say, “My employer didn’t change my benefits, didn’t take away my 401k match, my PTO stayed the same — I want to work for that company.” That’s what it should be.
Geoff: It does feel like a dangerous game for employers to make long-term benefits decisions based on what they feel is doable in a favorable labor market rather than what shows they actually care. But there have to be some bright spots. Where have you seen companies still doing things that show they genuinely care?
Jamie: I’m going to brag on Wellable real quick — you all did not pay me to say this, I am recording this for free. I noticed in one of your emails that you have summer Fridays, and I thought that was such a cool thing. Because you just don’t see that very often anymore. I haven’t had a summer Friday since probably 2014 or 2015. That’s a big deal. There are still companies out there letting people jet off on a Friday afternoon and say, “Hey, have a good weekend. It’s the summer. Go relax somewhere.” I love that.
Geoff: I appreciate that. It’s been in place since I joined about seven years ago, and it’s been very popular with the team. Maybe because of our roots in Boston, the summers are shorter and you really want to enjoy the sunlight and long days while you have them. We felt like it made a big difference on the overall happiness and wellbeing of our team, and it’s something that’s manageable with the right processes in place to make sure we’re still getting our work done.
It connects to a personal obsession of mine right now: the four-day work week. There have been some really successful trials internationally, and with all the productivity gains being attributed to AI, I do think there could be a version where that becomes more attainable than ever. Whether it’s summer Fridays or a true four-day week, it could be more of a reality in our lifetime than we once thought.
Jamie: Yes, I love the idea of a four-day work week. I read somewhere that 40-plus year olds especially need it, and I’m in my forties. I could totally get my normal 40-plus hour work week done in four days. Easy. Please.
Geoff: And the studies from pilot programs show the same, if not more, productivity. One more topic: the politically charged environment and how HR navigates that. What are your thoughts on how companies can set the ethos around politics in the workplace?
Jamie: I think this is a really challenging time. Everyone is entitled to their opinion, and I think it’s okay to have some friendly discussion in the workplace. That’s kind of what America was supposed to be. However, we do have to work with one another and find some sort of harmony. There is a fine line you have to walk.
I’ve worked at places that said no political conversation at all, and I was like, that’s a little insane. I do think it’s okay to have a conversation. But when it gets to the point where someone is wearing a hat or has a flag up or has things in their office that are offensive to other people, we need to have a conversation. Because it not being offensive to you doesn’t mean it’s not offensive to someone else. This is work. This is not your house or your car. That’s where policies about how you decorate your workspace come into play.
A lot of times those policies exist because someone did something crazy to their office or cube, so they had to enact a policy. It’s really walking a fine line: respecting people’s opinions while also being able to have healthy conversations. Unfortunately, what I see a lot is things getting so heated. People online are so quick to jump to extremes. And I see people constantly getting doxxed and it getting sent to their workplace. Just be careful out there, because next thing you know you’ll say something online and it ends up at your job.
Geoff: And the game has totally changed with the shift to more hybrid work and the advancement of social media. Organizations are increasingly viewing their staff as a representation of the brand. A company may have policies that if you’re identifying yourself as an employee on Facebook, you are a representation of the brand, and taking strong stances on topics might fall afoul of those policies. That’s why it’s even more important to clarify and communicate them, because somebody on a Saturday might not be thinking about their policy restrictions when they have their company tagged.
Jamie: Yeah. I actually saw this week that a North Carolina man was caught on video in a road rage incident going on a racist tirade — but he had his work shirt on with the logo. Of course he got fired. When I was employed, I also had someone reach out anonymously about a TikTok where someone said they didn’t believe in COVID, and she was a nurse at my healthcare company. I did some digging — it turned out to be someone with the same name, different person. But yeah, people love to dox others. And even myself, employees would sometimes report my meme content to management. They had no idea if I made it on the weekend or scheduled it in advance. I get it. But sometimes people are just looking to poke the bear.
Geoff: Is the transition into content and entrepreneurship something that kind of led you away from the traditional corporate HR path?
Jamie: Yeah, for sure. When I was laid off in April 2025, I was devastated. It’s all I had done for 23 years. I went through a really weird, dark phase where I didn’t realize how tied to my job I was, how much I needed to feel needed. I thoroughly enjoyed being able to assist people, even the simple things, even as a director. It was just a weird shift I had to go through.
I’ve looked for another job and done some consulting, but I’ve really tried to focus on making whatever I’m doing work, which is the memes and podcasting. I don’t know what the future holds, but I know this job market is kind of a nightmare right now. Maybe this is not the best time to try to find another job. And that’s okay. I’m just going to try to do whatever this is in the meantime.
Geoff: Love that. For all the folks listening, where is the best place to find your memes and your podcast?
Jamie: The podcast is called HR Besties. You can find us anywhere you listen to podcasts. We are the number one HR podcast! It’s with two other incredible ladies: Ashley Hurd at The Manager Method, and Lee Henderson at HR Manifesto on Instagram. I’m mostly on Instagram but also on Facebook and TikTok at humorous_resources, at millennial_misery, or if you want to follow me personally, that’s at the_chief_meme_officer.
Geoff: That one’s easy to remember. Jamie, thank you so much for joining the podcast today. And for everyone listening to Wellable Weekly, you can find us on Apple Podcasts, Spotify, or wherever you get your podcasts. Thank you.
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