Exclusive Interview With Josh Gottesman, CHRO, Orthodox Union
Posted on 04-16-2025, Read Time: 5 Min
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Where do HR leaders draw inspiration from? What are their worst nightmares? How did they stand the test of the changing times?
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Josh Gottesman is the Chief Human Resources Officer at Orthodox Union. He plays an integral role in all people strategies, global recruitment efforts, professional development activities, and compliance across the organization. He has been a corporate trainer and facilitator for 12+ years and is especially skilled at building effective, productive, and working relationships with client and staff. He has an MBA in Industrial Organizational Psychology and HR Management and is a Senior Certified Professional in the Society for Human Resources Management. Most importantly, Josh is the proud father of four JEC students. |
In an exclusive interview with HR.com, Josh reflects on how saying "yes" to opportunity and staying relentlessly curious helped shape his rise through the HR ranks. He also shares insights on using data to drive employee engagement, building culture in hybrid environments, and why flexibility, recognition, and internal mobility are the future of talent strategy.
Excerpts from the interview:
Q: What has your HR journey been like and what influenced you the most to have a positive impact on your career?
Josh: My HR journey started with an internship — a bit later in life than most. I had just pivoted careers, was finishing up my master’s in HR management and I/O psychology, and had a newborn at home. I didn’t know exactly where things would lead, but I knew I wanted to get into HR.
That internship at the Orthodox Union was my foot in the door, and from there, I just kept saying “yes.” I moved from intern to HR specialist, then to compensation, talent management, HR manager—and eventually, CHRO.
The biggest influence on my career has been the fact that people gave me opportunities — and I didn’t take a single one for granted. My philosophy was simple - master your current role so you can take on more responsibilities. I listened in on meetings, I asked questions, and I tried to add value wherever I could. I really believe that if you’re open, eager, and willing to grow, good things happen.
That internship at the Orthodox Union was my foot in the door, and from there, I just kept saying “yes.” I moved from intern to HR specialist, then to compensation, talent management, HR manager—and eventually, CHRO.
The biggest influence on my career has been the fact that people gave me opportunities — and I didn’t take a single one for granted. My philosophy was simple - master your current role so you can take on more responsibilities. I listened in on meetings, I asked questions, and I tried to add value wherever I could. I really believe that if you’re open, eager, and willing to grow, good things happen.
Q: What is your biggest challenge at this moment? How do you plan to address it?
Josh: Right now, my biggest challenge — and honestly, one of my biggest wake-up calls — came from our people analytics. We realized that more than half of our workforce has been with us for three years or less. That’s a huge shift, and it made me stop and think: If this is my future leadership team, am I doing enough to prepare them?
Digging deeper, the data also showed clear attrition points — employees were leaving around the 6-month and 18-month marks. That told me we weren’t just losing people; we were losing potential. So, we got to work. We built a new manager training program to strengthen leadership early, and we reimagined our performance management process to include five annual touchpoints instead of the typical one or two. Two of those are dedicated solely to career conversations — no ratings, no reviews, just real discussions about growth, goals, and the future.
It’s made a real difference. People feel seen, supported, and invested in. And while we’re still learning, I’m confident we’re building a stronger, more loyal pipeline of future leaders from within.
Digging deeper, the data also showed clear attrition points — employees were leaving around the 6-month and 18-month marks. That told me we weren’t just losing people; we were losing potential. So, we got to work. We built a new manager training program to strengthen leadership early, and we reimagined our performance management process to include five annual touchpoints instead of the typical one or two. Two of those are dedicated solely to career conversations — no ratings, no reviews, just real discussions about growth, goals, and the future.
It’s made a real difference. People feel seen, supported, and invested in. And while we’re still learning, I’m confident we’re building a stronger, more loyal pipeline of future leaders from within.
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Name: Josh Gottesman
Designation: CHRO, MBA, SHRM-SCP
Company: Orthodox Union
Total number of employees: 1,100
When did you join the current company: 2014
Total experience in HR: 12 years
Hobbies: Smoking meat and hanging out with my family
What book are you reading currently: Anything I can get my hands on.
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Q: How do you see workplace culture evolving over the years?
Josh: I think workplace culture has shifted from being something you “inherit” to something you actively build. It used to be all about what happened in the office — team lunches, birthday cakes in the breakroom, that kind of thing. Now, culture has to live in the experience, not the location.
People want clarity, purpose, and connection. They want to know how their work matters and that their growth is a priority. I’ve seen culture evolve into something much more intentional. It’s about creating an environment — whether in-person or remote — where people feel like they belong, like they’re growing, and like their voice counts.
At our organization, we’ve leaned into that shift by focusing on feedback, development, and making sure employees feel heard. Culture isn’t just HR’s job — it’s everyone’s responsibility. The best cultures are the ones where people don’t just feel like part of a team, but part of something bigger.
People want clarity, purpose, and connection. They want to know how their work matters and that their growth is a priority. I’ve seen culture evolve into something much more intentional. It’s about creating an environment — whether in-person or remote — where people feel like they belong, like they’re growing, and like their voice counts.
At our organization, we’ve leaned into that shift by focusing on feedback, development, and making sure employees feel heard. Culture isn’t just HR’s job — it’s everyone’s responsibility. The best cultures are the ones where people don’t just feel like part of a team, but part of something bigger.
Q: Can you share the top three learnings from the challenges you faced?
Josh: I’ve learned a lot through challenges — some expected, some not — but a few lessons have really shaped how I lead today:
1. Don’t underestimate the power of learning through osmosis.
If you're early in your career or trying to grow into a leadership role, one of the best things you can do is just be in the room. Ask to shadow meetings. Listen in on the big conversations. You might not contribute right away, and that’s okay. Just being present will give you a window into how decisions are made, how leaders think, and how organizational culture really works. I learned more from quietly observing than I did from any textbook or training.
2. Say yes to challenges—even when they scare you.
Growth doesn’t come from staying in your comfort zone. Some of my biggest learning moments came when I took on projects I didn’t feel fully ready for. And yes, I made mistakes. But those moments taught me how to recover, reflect, and get better. If you’re leading others, challenge them with stretch assignments — and create the kind of environment where failure isn’t feared, it’s expected and supported. That’s how future leaders are built.
3. Share the credit—loudly and often.
Recognition is powerful. One of the best lessons I learned is that a great leader doesn’t just accept credit — they share it. When someone on your team contributes to a project, make sure their name is mentioned. Let them shine. That kind of recognition builds trust, loyalty, and confidence. It also creates a culture where people want to step up and lead, because they know their contributions will be valued.
1. Don’t underestimate the power of learning through osmosis.
If you're early in your career or trying to grow into a leadership role, one of the best things you can do is just be in the room. Ask to shadow meetings. Listen in on the big conversations. You might not contribute right away, and that’s okay. Just being present will give you a window into how decisions are made, how leaders think, and how organizational culture really works. I learned more from quietly observing than I did from any textbook or training.
2. Say yes to challenges—even when they scare you.
Growth doesn’t come from staying in your comfort zone. Some of my biggest learning moments came when I took on projects I didn’t feel fully ready for. And yes, I made mistakes. But those moments taught me how to recover, reflect, and get better. If you’re leading others, challenge them with stretch assignments — and create the kind of environment where failure isn’t feared, it’s expected and supported. That’s how future leaders are built.
3. Share the credit—loudly and often.
Recognition is powerful. One of the best lessons I learned is that a great leader doesn’t just accept credit — they share it. When someone on your team contributes to a project, make sure their name is mentioned. Let them shine. That kind of recognition builds trust, loyalty, and confidence. It also creates a culture where people want to step up and lead, because they know their contributions will be valued.
Q: Where do you draw inspiration from? What do you say to those struggling to find a place in the boardroom?
Josh: A lot of my inspiration actually comes from my background in theater and choreography. That experience taught me to think in terms of what happens on stage — what people see — and backstage — everything that goes on behind the scenes to make it work.
That lens helps me look at challenges creatively. In HR, we’re often behind the curtain, but I’ve learned that how something is experienced matters just as much as how it’s built. If you’re sitting in the audience, what’s the story we’re telling? What message are we putting out there? That mindset keeps me focused on clarity, purpose, and communication that resonates.
And when it comes to the boardroom, the best advice I ever got was this: It’s not about how much you say — it’s about being remembered. Your goal shouldn’t be to fill the space; it should be to say something that sticks. I always remind myself to listen closely, take in the room, and then speak up with something meaningful. One golden nugget that lands well can carry more weight than five minutes of talking. That’s how you earn your seat at the table — and keep it.
That lens helps me look at challenges creatively. In HR, we’re often behind the curtain, but I’ve learned that how something is experienced matters just as much as how it’s built. If you’re sitting in the audience, what’s the story we’re telling? What message are we putting out there? That mindset keeps me focused on clarity, purpose, and communication that resonates.
And when it comes to the boardroom, the best advice I ever got was this: It’s not about how much you say — it’s about being remembered. Your goal shouldn’t be to fill the space; it should be to say something that sticks. I always remind myself to listen closely, take in the room, and then speak up with something meaningful. One golden nugget that lands well can carry more weight than five minutes of talking. That’s how you earn your seat at the table — and keep it.
Q: How do you draw the line to achieve work-life balance?
Josh: For me, work-life balance starts with expectations. And I don’t just mean setting them — I mean talking about them. One of the most important things I’ve learned is that if expectations aren’t clear, people will default to assuming the worst: “I should be online 24/7,” or “I can’t take that time off.” That’s not healthy for anyone.
That’s why my email signature says, “I respect your work-life balance. My working hours may not be your working hours. Please don’t feel obligated to reply outside of your normal work schedule.” It’s a small line, but a powerful message. It signals that I’m not just saying I value balance — I’m modeling it and creating space for others to do the same.
I always tell my team: If you’re not sure what the expectation is, ask. Balance starts with clarity and honest conversations. It doesn’t mean we don’t work hard — it just means we do it in a way that’s sustainable, respectful, and human.
That’s why my email signature says, “I respect your work-life balance. My working hours may not be your working hours. Please don’t feel obligated to reply outside of your normal work schedule.” It’s a small line, but a powerful message. It signals that I’m not just saying I value balance — I’m modeling it and creating space for others to do the same.
I always tell my team: If you’re not sure what the expectation is, ask. Balance starts with clarity and honest conversations. It doesn’t mean we don’t work hard — it just means we do it in a way that’s sustainable, respectful, and human.
Q: What fundamental change(s) (in terms of culture) have you brought into your company?
Josh: One of the most fundamental shifts we made was transforming HR from a support department into an operations department. We moved from being reactive — handling issues as they came — to being proactive and strategic. Today, people initiatives are front and center in almost every major conversation across the organization.
How did we get there? We focused relentlessly on showing our value-add. Every initiative, every program, every conversation — we asked ourselves, What’s the value this brings to the organization and to our people? And we made sure others could see it, too.
Whether it was rolling out structured manager training, overhauling our performance management process, or launching career development conversations, we didn’t just implement — we communicated the why behind it. That helped us earn trust and a seat at the table.
Now, people don’t see HR as a back-office function. They see us as an operational engine that drives culture, performance, and growth.
How did we get there? We focused relentlessly on showing our value-add. Every initiative, every program, every conversation — we asked ourselves, What’s the value this brings to the organization and to our people? And we made sure others could see it, too.
Whether it was rolling out structured manager training, overhauling our performance management process, or launching career development conversations, we didn’t just implement — we communicated the why behind it. That helped us earn trust and a seat at the table.
Now, people don’t see HR as a back-office function. They see us as an operational engine that drives culture, performance, and growth.
Q: What are the major trends you see affecting HR in the next few years?
Josh: One of the biggest trends I see shaping the future of HR is the challenge — and opportunity — of managing a multi-generational workforce. We now have four, sometimes five, generations working side by side. That means a wider range of expectations, communication styles, work habits, and values than ever before.
Gen Z might prioritize flexibility and feedback. Millennials often want purpose and growth. Gen X may value autonomy, while Boomers bring institutional knowledge and loyalty. And they're all in the same meetings, trying to collaborate and deliver results.
This can create friction — but it can also be a huge advantage if managed well. HR has to play the role of translator, bridge-builder, and coach. We have to help leaders and teams understand each other’s perspectives, adapt their communication styles, and create environments where everyone feels seen and valued — regardless of age or background.
It’s not about catering to each generation separately. It’s about building a culture of mutual respect, continuous learning, and adaptability. If we get that right, we don’t just reduce conflict — we unlock incredible creativity and innovation.
Gen Z might prioritize flexibility and feedback. Millennials often want purpose and growth. Gen X may value autonomy, while Boomers bring institutional knowledge and loyalty. And they're all in the same meetings, trying to collaborate and deliver results.
This can create friction — but it can also be a huge advantage if managed well. HR has to play the role of translator, bridge-builder, and coach. We have to help leaders and teams understand each other’s perspectives, adapt their communication styles, and create environments where everyone feels seen and valued — regardless of age or background.
It’s not about catering to each generation separately. It’s about building a culture of mutual respect, continuous learning, and adaptability. If we get that right, we don’t just reduce conflict — we unlock incredible creativity and innovation.
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