Building Credibility from Scratch
What Eli Kamerow Did to Break into HR Tech
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What were you doing before you pivoted into HR tech, and what sparked your interest in making the leap?
My background was all business development and go-to-market work for startups. Lots of CPG, web3/crypto, and SaaS. I never would have guessed that I would end up in HR tech. I met one of the founders of Darwinbox while doing some consulting. Over 6 months of working side-by-side and diving into the industry, I knew it was an opportunity I couldn’t pass up. One of the most exciting things about HR tech is that it touches every single employee. As a competitive person, it’s hard to look away from the scale of that problem and solution.
At the time, did it feel like a bold move, a lucky break, or something else entirely?
It felt like the right time. Having spent half a decade in the legal tech industry, I noticed similarities between how the General Counsel role is evolving (driving growth in legal tech) and how the CHRO role is evolving (driving growth in HR tech). This was when companies were still rethinking what employee experience should look like in response to the global pandemic, and there hadn’t been a new enterprise entrant since Workday. The timing felt right to take the plunge.
What was your biggest fear or hesitation about switching industries, and how did you work through it?
I feared not knowing anything and not being credible (two sides of the same coin). Even with 6 months of consulting and daily conversations with some of the brightest people in the industry, I knew that I wanted to learn more. Credibility is everything in sales, and I knew it would be a challenge to sell and advise if my expertise wasn’t there. There wasn’t a shortcut to work through it, just lots of learning, falling on my face, and repeating the cycle.
What skills or experiences from your previous roles proved unexpectedly transferable?
I’m a quick learner. In the early days, it wasn’t uncommon for me to be introduced to a term or a concept in the morning, learn about it over lunch, and then add that concept to my toolbox later that same day.
The other experience that paid unexpected dividends was my experience in the legal tech industry. Companies shifted from viewing \ the legal function as a cost center to strategic partners. This shift changed everything in the legal tech industry. A similar shift started for the HR function and CHRO/CPO leading up to, and then rapidly accelerated by, COVID-19. Understanding the history of another industry helped me navigate some of the massive shifts happening in HR.
Was there a moment when you felt like, “I belong here now”? Or did it take a while?
It’s easier to highlight moments when I felt I would never fit in. There was one early call a few months in, where the executive knew our COO/co-founder. Immediately after hanging up, he called our COO and said “Why’d you hire that guy? He’s an idiot.” Our COO just laughed and reminded me that there was a lot to learn.
Moments like that continue to keep me humble, even though it was 3+ years ago. One moment that stands out, that made me feel like I belonged, happened after a couple of years in the industry. I was introduced to an executive at a $6B company for an important project. We disagreed on some points, but had a productive conversation, and the executive agreed to do things our way. After hanging up the call, I remember thinking “hmm..that went well. If I can hang with that guy, maybe I have learned a few things.”
What was the steepest learning curve during your early days in HR tech?
Learning enough to sound credible. Before joining Darwinbox, I was only an end-user of HR tech. There was a ton to learn about the products/competitors, the craft of HR, and all the parts of the employee lifecycle that make up a majority of what HR teams work on every day.
Beyond that, there was all the industry context that was second nature to my peers. It’s one thing to make a joke about Frankenstein’d systems creating reporting challenges for UKG. It’s another to be able to understand the history of the Ultimate and Kronos merger, and another level of depth to point out the specific challenges on a module-by-module basis. Credibility is incredibly important to Darwinbox because no one in the US market knew who we were. A rep at Workday or Oracle could afford not to have every answer because they had their brand behind them. I couldn’t trade on company credibility, I had to bring my own.
Did you seek out mentors, communities, or learning resources to help you adjust? What made the biggest difference?
All of the above. Going to distant connections and asking them if I could “ask a few dumb questions to a friendly face.” Going to HR events and meeting people. Seeking out other industry vets and asking them questions. As I learned more, the mental map became more complete, and connections started to become clear. This, in turn, would identify where I needed to go deeper next. One person I spoke to would recommend another. One concept I read about required getting smart about a related concept. It became a flywheel. The average person we hire on our team has 20+ years of industry experience. Learning from those folks has been invaluable.
How did the people around you—colleagues, friends, family—respond to your career change?
I’m lucky to have a supportive network of friends, family, and colleagues. While I was changing industries, I was still chasing startups and doing business development, so it didn’t seem like a crazy pivot. It’s not uncommon for salespeople to jump industries like I did.
What’s one thing you now appreciate about the HR tech space that you didn’t know when you started?
How small this industry is, everyone knows everyone! I also didn’t properly weigh how drastically AI would increase the size of the industry. It’s still a couple of years away, but I expect the HR tech market will double once every employee has a personalized, agentic HR Business Partner bot in their pocket.
Looking back, do you think an industry shift was more about timing, preparation, or mindset?
Timing and mindset. When I got connected to the Darwinbox founders, it was clearly the right time to get into this industry. I was also looking for growth opportunities, so I’d call that a mindset.
What advice would you give to someone who’s interested in entering a new field, but worried they don't have the "right" background?
Don’t make a complete leap; find some similar things. For example, I was entering a new industry, but I was doing the same type of work for a similar type of company.
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