?You never know where a chance encounter might lead. For Josh Gottesman, SHRM-SCP, a lucky meeting led to an internship at age 27 that, nine years later, propelled him into his current role as CHRO at Orthodox Union (OU).
It was 2012 and Gottesman was the director of American operations for NCSY—a Jewish youth group under the auspices of OU. OU, headquartered in New York City, is the world’s largest global Jewish nonprofit organization, with offices in Los Angeles and Jerusalem. 
As director of American operations, Gottesman served as one of the bus directors during NCSY’s summer program, “The Jerusalem Journey.” The buses tour Israel and each bus director oversees their tour guide and advisors and is responsible for the 40 teenagers on the bus.
It was during the summer program that Gottesman met Lenny Bessler, the CHRO of OU, who was visiting the program. When Bessler learned Gottesman was pursuing a master’s degree in HR management and industrial psychology, he invited Gottesman to reach out “if I ever needed help navigating HR as a career,” Gottesman recalled.
A year later, Gottesman left NCSY to become department head of student life at Rae Kushner Hebrew Academy in Livingston, N.J., but he was unhappy there and left after 11 months.
Newly married with a baby on the way, Gottesman fished out Bessler’s business card and called him. One month later, he was working a seven-week HR internship at OU.
After completing the internship, Gottesman progressed through the ranks at OU:
- * HR specialist in 2014.
- Talent management specialist and senior compensation analyst in 2015, when he also completed his master’s degree.
- HR manager in 2017.
- Assistant director of HR in 2019.
- Associate HR director in 2022.
- CHRO in 2023, after Bessler approached the organization’s senior leadership and endorsed Gottesman as his successor.
Today, Gottesman oversees six full-time HR employees, with plans to fill a talent management role and add an HR fellow to the staff.
“I started my career in HR later than most because I went through a career change. I originally wanted to do outreach when I was working in NCSY, but when I was pursuing my MBA, I decided to explore the world of HR,” he said.
SHRM Online spoke with Gottesman about his HR journey. Responses have been edited for clarity and brevity.
SHRM Online: When you contacted Bessler looking for work, two years had passed since you last spoke. How did you approach the conversation?
Gottesman: It was almost like a cold call. I just felt desperate to use all the connections I had to get into the HR world. It helped that I had worked within the organization and knew some names I could drop.
I was very open and honest with him. I told him: I’m looking for a job. I want to get experience. I’m willing to do any work that you have. I need to grow my career. Do you have any opportunities for me?
It was summer and he told me they could take me on as a paid intern. The HR department consisted of four full-time employees, a part-time worker and me. I also had a second, unpaid internship at a real estate start-up company, but it didn’t involve real HR work, and I left after six weeks.
SHRM Online: What did your OU internship entail?
Gottesman: Cleaning up and refining job descriptions, building organizational charts. It involved a lot of research of other job descriptions and job postings to see what other organizations were doing. Sometimes it was mind-numbing, but it was a good experience learning the organization and the different job levels and positions there.
SHRM Online: Take us through your career progression there.
Gottesman: A full-time employee was leaving as my internship ended, and I was offered her job.
I started branching into other departments within the HR world. One of my focuses was improving processes and making them more efficient. I was exposed to benefits and attendance and worked with the HR manager on disability and visa concerns. At the time, I was the tech-savvy person of the department, using different software and technology.
We didn’t have a talent-development strategy, and I went to Lenny and said, “I think I could do a good job with training.” The first employee training I did was how to use LinkedIn and create a profile. I slowly worked myself into the talent strategy world. I became a corporate trainer and ran sessions. Throughout that experience, I was meeting people, networking.
SHRM Online: You have credited Bessler with fostering an environment that allowed you to learn from your failures and mistakes and receiving support and guidance Please share an example of how he did that.
Gottesman: I once sent an email to the entire company that contained wrong information and the wrong people received it. Sometimes failure happens; you’re learning the job.
Lenny’s approach was, “How can we fix this?” Then I fixed it. He believed it’s important to get experience and know all the different areas of HR. Our whole culture is about learning so you can be a better HR professional. You own up to your mistakes and move on. Most importantly, you learn from your mistakes.
And Lenny always did a debrief after any session or program about what worked, what didn’t.
SHRM Online: What is some career advice you have for other HR professionals?
Gottesman: If you want to grow your career, don’t be afraid to ask for work outside your work responsibility. That was key for me. I was not the expert in benefits, but I became an expert in benefits.
I also was lucky in working for a small HR department because I was forced to learn other areas of HR than what I was specifically hired for. That came from me saying, “I’m good where I am with my current job role; now, I need to add to my portfolio and grow my skills.”
Also, I learned through osmosis. I sometimes just sat in a room and listened to a discussion—compensation, a benefits renewal contract. Sometimes you need to ask permission to do that, though. You’re showing you want to learn more.
And I tried to find one or two solid points I could bring up if I was called on during the meeting so I could add value. When you do that, make sure it’s meaningful.