You Deserve a Six-Week Sabbatical | Working (Remotely) at Redox

In this episode of Culture Uncovered, Jena Dunay sits down with Chloe Drew, Chief People Officer at Redox, to explore what it takes to build a thriving remote-first culture while helping power the healthcare ecosystem behind the scenes.

Chloe shares Redox's journey from a startup founded by former Epic employees into a leading health data interoperability platform that enables healthcare organizations to securely exchange critical information. She also discusses how the company has maintained its people-first philosophy while scaling, why humility and customer obsession are central to the culture, and what makes Redox's remote model successful.

They also discuss the challenges of growing a distributed organization, the importance of internal mobility, lessons learned from executive hiring, and the qualities that help employees thrive in a fast-moving, highly collaborative environment.

What You'll Learn

•  How Redox became the "plumbing and piping" behind healthcare data exchange and why interoperability matters for the future of healthcare. 
•  What it takes to build and sustain a strong culture in a fully remote company spanning more than 25 states. 
•  Why Redox's values refresh was a company-wide effort—and how employee ownership helped shape the next chapter of the culture. 
•  How internal mobility creates career growth opportunities even without a large formal learning and development program. 
•  The traits that help employees thrive at Redox, including curiosity, humility, accountability, and comfort with ambiguity. 

Guest Highlights

• Industry: Healthcare Technology / Health Data Interoperability 
• Founded: 2012 
• Employees: ~130 
• Funding Stage: Series D 
• Work Model: Fully remote with employees across 26+ states 
• Headquarters Roots: Madison, Wisconsin 
• Mission: Simplifying and accelerating healthcare data exchange across the healthcare ecosystem 

Unique Perks & Programs

• Fully Remote by Design — Remote-first since before COVID, allowing employees to live and work where they thrive while accessing talent nationwide. 
• Flexible Time Off — Open PTO philosophy built on trust, with leaders actively encouraging employees to recharge. 
• Six-Week Paid Sabbatical — Employees receive a six-week sabbatical every five years to rest, reset, and return refreshed. 
• Strong Internal Mobility Culture — Every role is posted internally, and employees are encouraged to explore new functions and career paths. 
• Company-Wide Values Refresh — Employees at every level participated in redefining Redox's core values, creating shared ownership of culture. 
• Regular In-Person Connection Opportunities — Team gatherings, customer events, executive offsites, and company-wide retreats help maintain strong relationships in a remote environment.

To learn more about Redox:

Careers Page (They're hiring!)
LinkedIn Page
Chloe's LinkedIn

Transcript

Jena Dunay: Hello friends, and welcome back to another episode of Culture Uncovered, where we go behind the scenes of very cool companies to work for. I have the honor and privilege today of talking with the Chief People Officer of Redox, Chloe Drew. Thank you so much for joining me today, Chloe.

Chloe Drew: I am so excited to be here. This is really just a gift on a Friday. I love this. Thank you for having me.

Jena Dunay: It is a gift on a Friday. We're recording on a Friday, talking about our weekend plans. So hopefully if you're listening to this, it's probably a Wednesday—but maybe you're listening on a Friday and getting ready for your weekend too.

Let's get started with the basics. What does Redox do? For anyone who may not have heard of the company before, tell us a little about it.

Chloe Drew: Absolutely. Redox is a health data interoperability platform, which sounds very fancy and complicated. Essentially, it means that we move health data around the healthcare ecosystem.

Jena Dunay: Okay, that's much simpler than what you originally said. When you started with "health data interoperability platform," I was thinking, I'm not smart enough to know what that means.

Chloe Drew: Exactly. We're a little more sophisticated than that description suggests. My CEO, when he arrived, said, “I get it—we're the plumbing and piping for health data.” That's simple and makes total sense. It's not the sexy work, but it's the essential backbone of the healthcare ecosystem.

Jena Dunay: I love that. Tell us a little bit about the company. How long have you been around? What's the founding story?

Chloe Drew: I actually love the founding story. Three pretty young guys were working at Epic, which everyone knows is a huge player in healthcare technology. One of the things they realized was that health data doesn't really talk to itself.

Jena Dunay: That's not totally shocking to me.

Chloe Drew: Exactly. Every one of us as patients has experienced this. The way healthcare data was coded and exchanged created a lot of friction. So they left Epic and founded Redox 12 years ago.

Today we're a Series D company. We started by working with small and medium-sized software vendors, and now we work with some of the biggest healthcare providers and organizations in the country. We've become a critical part of the infrastructure supporting many major healthcare players.

Jena Dunay: That's so cool. I love organizations that people may never have heard of, but they've likely interacted with them in some way because they're the behind-the-scenes player. They're what I call "spotlight adjacent"—not in the spotlight themselves, but enabling everything behind it.

How big is the company today?

Chloe Drew: We have about 130 employees. One of the coolest things about us is that we're entirely remote. Last I checked, we had employees in 26 or 27 states. My team is spread all over the country. The executive team is spread all over the country. It makes for a really interesting environment.

Jena Dunay: Tell me about that. What was the reasoning behind staying remote?

Chloe Drew: I'm probably going to get some of the company lore slightly wrong, but my understanding is that the founders chose to be fully remote even before COVID.

Part of the rationale was that they cared deeply about their lives, their families, and their dogs. They wanted to build a company where work was important and meaningful, but where people also had full lives outside of work.

The other reason is one I strongly believe in—you can access the best talent from anywhere. We have employees living all over the country, not just in major coastal cities. I live in New York, which is an expensive market and ultimately a relatively small talent pool if that's your only hiring geography. Being remote allows us to hire incredible people from everywhere.

Jena Dunay: I love hearing why companies choose the work models they do. Every organization has a different rationale.

Is there a headquarters? Do people ever get together in person?

Chloe Drew: There's no formal headquarters. The heart and soul of Redox is probably Madison, Wisconsin. Many of the early employees came out of Epic, so there's still a bit of a connection there.

We do have some coworking space in Madison. In fact, we recently held our first company-wide offsite in three years there. It felt really special to bring everyone together in the city where the company began.

People definitely get together. The field team has sales kickoffs and field events. The executive team meets monthly in person, which we've been doing since our new CEO arrived two years ago. Teams also gather around conferences and customer meetings.

There's enough in-person interaction to build relationships, while still allowing people to live their lives in ways that work for them.

Jena Dunay: It sounds like a really flexible middle ground. You're acknowledging that in-person connection matters while still allowing people to structure their lives in a way that works for them.

Chloe Drew: Exactly. I personally care a lot about in-person interaction because it's great for relationship building, and I get a lot of energy from it as an extrovert.

But one of our core values is customer obsession. Our CEO, Tripp Hofer, talks about this all the time. Sales and customer relationships are built on trust, and it's much easier to build trust when you've sat down with someone and broken bread together.

That's why our sellers spend time with customers in person. We visit clients, attend conferences, and build those relationships. Things move much faster when you're face-to-face with customers.

Jena Dunay: Especially in the age of AI, being more human and more three-dimensional is becoming a differentiator.

You've been with Redox for about four years. What made you join?

Chloe Drew: I won't go through my entire career arc, but I grew up professionally in the social sector. I worked in politics, foundations, city government, and nonprofits. I never worked in the private sector until about five years ago, when I joined Compass Real Estate.

What I found at Redox was a sweet spot. We're a for-profit company, but we're working in healthcare, which aligns with many of the things that matter deeply to me. People here genuinely care about improving healthcare outcomes.

Healthcare data is also incredibly important for the future of machine learning and AI, so we're solving a meaningful problem in a highly technical and forward-looking way.

I'll never forget my interview process. It was the best candidate experience I'd ever had. Every conversation was with someone who was smart, warm, funny, and deeply impressive. I kept thinking, "I didn't expect this company to be for me," and then every interaction reinforced the opposite.

Even though we have a new CEO now, that feeling of belonging has remained.

Jena Dunay: Candidate experience really matters. We talk so much about sourcing strategies and recruiting tactics, but the foundation is the interview process itself.

How did you find the opportunity?

Chloe Drew: Through a search firm. I actually really like True Search. I've worked with them both as a candidate and as a hiring leader. I felt they did a great job representing both the company and the candidate honestly.

They introduced me to Redox, I met the founder and our general counsel, and I completely fell in love with the opportunity.

Jena Dunay: Tell me about the culture at Redox.

Chloe Drew: Before Redox, I worked at another remote company where I struggled to understand the culture. I wasn't sure if that was because it was remote or because the culture wasn't particularly distinct.

At Redox, I understood it almost immediately.

People are here for many of the same reasons. They care about healthcare. They understand that we're working on behalf of customers who directly impact patient outcomes.

We also have some of the most technically brilliant people I've ever worked with. There are conversations about healthcare interoperability and technology that are completely over my head, and I find that exciting.

At the same time, there's a warmth here. I've often worked for East Coast organizations that had a sharper, more competitive edge. Redox has a Midwestern soul. There's a deep humility across the company.

Our CEO cares a lot about humility. He wants us to brag about our customers, not ourselves. That mindset really influences the entire culture.

Jena Dunay: One thing you mentioned that stood out was that you laugh a lot at work.

Chloe Drew: We do. My people team is fantastic. We laugh constantly.

Honestly, in HR, you have to laugh.

The executive team genuinely enjoys each other. They're smart, capable people, but it's also a fun group. We enjoy working together.

Jena Dunay: What advice would you give to leaders trying to build culture in a remote-first environment?

Chloe Drew: The founders were incredibly intentional about defining what it meant to be "Redoxy." The culture was already distinct when I arrived.

When our new CEO joined, though, the company needed to mature. We needed to grow up and move upmarket.

One of the smartest things he did was lead a company-wide refresh of our values. It wasn't top-down. It was entirely grassroots.

The whole company participated. We discussed what energized us, what mattered most, and what kind of company we wanted to become. We moved from three values to five.

It wasn't perfect, but it gave everyone ownership over where the culture was heading. Then you have to reinforce those values constantly through communication and behavior.

Jena Dunay: Were those values more aspirational or descriptive?

Chloe Drew: A little bit of both.

For example, customer obsession became one of our new values. We had always served customers well, but I don't think we always embodied what customer obsession truly meant.

At the time, it was somewhat aspirational. We defined it clearly and spent two years reinforcing it. In our most recent engagement survey, people specifically noted how much more customer-focused we've become.

I like values that point you toward where you're trying to go.

Jena Dunay: What are some of the benefits and perks that employees appreciate most?

Chloe Drew: People really value our remote model. That's probably the biggest one.

We also offer flexible time off rather than a fixed PTO structure. People don't abuse it. If anything, we sometimes have to encourage people to take more time away.

We also offer a six-week sabbatical every five years, which is longer than many programs I've seen. Every time someone comes back from a sabbatical, they're refreshed and re-energized.

Most importantly, I think people feel that we respect the reality of their lives outside of work.

I have kids. I can drop them off at school, attend a parent-teacher conference, get work done, and still be successful professionally. My life is porous.

Jena Dunay: That's such a great way to describe it.

Chloe Drew: It really is. People have complicated lives. This model acknowledges that reality.

Jena Dunay: What does learning and development look like at Redox?

Chloe Drew: One thing we're actively improving is reinforcing our career frameworks. We built leveling frameworks a few years ago, but employees have told us they want more reminders about what growth and advancement look like.

We're planning to refresh and reinforce those expectations.

One thing we're surprisingly strong at is internal mobility. We're a small company, but we move people around a lot. Every role is posted internally, and employees are encouraged to raise their hands.

We've had recruiters move into customer success. We've had people explore entirely new functions.

We don't have a massive L&D budget or formal development academy, but we do create opportunities for people to grow through movement and new experiences.

We also recently brought in Sarah Goodpaster to lead field enablement. She's fantastic and has been doing incredible work developing our sales and customer success teams.

Jena Dunay: Internal mobility is such a powerful development tool.

Let's talk about something no company gets perfectly right. What are some areas you're still working on?

Chloe Drew: Onboarding is one.

We revamped our onboarding years ago, but we're a different company now. We have a new CEO, new products, and a different strategy. The onboarding experience needs a refresh to reflect that.

Another area where I've learned hard lessons is executive hiring.

The mistakes I regret most involve executive leaders we didn't fully pressure test. We have a rigorous hiring process, including exercises and assessments, but there have been times where we moved too quickly.

When you get an executive hire wrong, the impact is enormous. They hire people, shape culture, make strategic decisions, and influence the organization in profound ways.

Those are the moments where it's worth taking a few extra steps, even if it slows things down.

Jena Dunay: That's such an honest answer.

Who thrives at Redox, and who might struggle?

Chloe Drew: The people who thrive here are creative, scrappy, curious, and deeply motivated by solving problems.

We're a small, remote company. If you're someone who waits for instructions or expects a large infrastructure of support functions to guide every step, this probably isn't the right environment.

The people who do well lean into ambiguity. They take ownership. They find opportunities rather than waiting for them.

We're also incredibly cross-functional. The biggest projects involve product, marketing, customer success, and many other teams working together.

Humility matters too. Our CEO has strong expectations around accountability, integrity, and giving credit to others. People who struggle tend to be those who seek personal credit or engage in political behavior.

Being a good person genuinely matters here.

Jena Dunay: My grandmother used to say, "If you have to tell somebody, it doesn't count."

Chloe Drew: I love that.

Jena Dunay: Finally, if someone listening is interested in Redox, what does hiring look like right now?

Chloe Drew: We're hiring for a variety of roles. Some are backfills for long-tenured employees. Others are growth-driven positions, especially on the customer success side because demand is so strong.

All of our openings are listed on our website at redoxengine.com.

Our interview process is thoughtful. You'll meet the hiring manager, members of the team, and often complete an exercise relevant to the role.

For engineering positions, we want to see how you think through technical work. For executive roles, we use case studies and exercises to understand how you solve problems and collaborate.

The goal isn't free work. It's understanding how you think.

We're currently hiring for positions including a National Sales Director and several other roles across the company.

Jena Dunay: I actually love exercises when they're done thoughtfully. Many people aren't naturally great interviewers, but they can absolutely do the job. Exercises allow candidates to demonstrate their thinking and their capabilities in a more realistic way.

Chloe Drew: Exactly. The most interesting part isn't even the exercise itself. It's the conversation afterward. We get off script, start exploring different scenarios, and really see how someone thinks.

That tells you so much more about what it will be like to work together.

Jena Dunay: Chloe, this has been such a fun conversation. Thank you for sharing more about Redox, your culture, and your approach to leadership.

Chloe Drew: Thank you so much.

If you're interested in learning more about Redox, we'll have all the links in the show notes. And we'll see you next week on another episode of Culture Uncovered.

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