Sidebench Talent Spotlight: Daryl Keith Cristobal

Sidebench
8 min readAug 24, 2022

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Where did you grow up and what was it like?

I grew up in the Alum Rock foothills of San Jose, California. I had a pretty traditional upbringing where family was at the heart of everything. I would spend time with my family every waking occasion (aside from school, of course) and have vivid memories of Friday nights spent every week at my grandparent’s home in a town over when my cousins would also be over and we would play a game of “Pirates.” (Essentially, there are two teams. One team would build a makeshift fortress such that it would be hard to penetrate through, while the second team would use tennis balls to break through and try to “tag out” the other team. You can say these games got pretty intense!) Nothing like the good ole days!

It’s rather common that Operations folks have uncommon paths into the discipline. Walk us through the process that you went through to get into Operations.

My path towards becoming an HR practitioner became all too clear even before receiving my college diploma, a rather unusual career, I had thought at the time, for someone who was graduating with a Political Science major. I had envisioned attending law school and becoming a licensed attorney here in California, but it was not until I was afforded the opportunity to study abroad my Fall semester of senior year and take up some law courses at the University of Manchester that I experienced an epiphany. As much as I enjoyed my courses, I could not fathom the idea of being in the books for an additional three years after undergrad reading legal jargon day-to-day, so I thought I had to find a way out and make a switch.

Luckily for me, I had the opportunity during the summers after my freshman, sophomore, and junior years of college to intern at the Pacific Gas & Electric Company (PG&E), where I was able to develop my foundational knowledge of HR, specifically within the areas of Recruiting, Immigration, and Global Mobility. I can legitimately express that this opportunity “fell on my lap,” and I owe it to Dr. Tommy Moreno, PG&E’s University Programs Manager at the time, who reached out my spring semester of freshman year checking in on me and seeing if I would be interested in interning with the company, albeit in HR. Opportunities like these are hard to pass up on, especially as a college freshman, so I thought to myself, “why not.” (Backstory: Like many high school seniors, I had applied for scholarships and I just so happen to have been a recipient of a PG&E scholarship, hence the outreach.)

The opportunity I had to intern at PG&E for three summers and develop the requisite skills needed to become an effective HR practitioner was surely my calling. It did not take me long to realize that I could channel my passion for advocating for people in a really fulfilling way, and it has been everything I have wanted in a role thus far.

We talk a lot about our jobs being the opportunity to imagine the future and then make it real. What vision do you have for the future and want to make real?

What these last few years have shown is that the traditional mode of working has fundamentally changed and employers are needing to balance flexibility with specificity to ensure team members have the guidance needed to live their lives and work remotely. We have come a long way since and the People Operations (HR) organization has been at the forefront in supporting its team members and catalyzing changes in the workplace.

I, like many other HR practitioners, were put in positions where we had to rethink, reimagine, and reconsider how we foster talent, deliver key services, and ensure our team members are well taken care of to weather through these unprecedented conditions. We have also had to take iterative approaches — setting clear expectations about how we approach this new way of work, acknowledging that things are likely to evolve and adapt over time, “experimenting” with new policies and program, assessing whether we are achieving our desired goals, and then re-starting the process all over again. Countless runs of experimentation to get it “right.”

As COVID now becomes part of our “new normal,” things are unlikely to go completely back to the way they once were. As I think about the future, remote work is likely here to stay. I believe now is the time to seize the opportunity to promote flexiwork by introducing new structures that enhance work flexibility and developing processes and programs that keep team members engaged, connected, and productive. At the end of the day, we are all humans in different places in our lives and careers. I recognize that how and where we work can make a big difference in how one shows up in work and in life and I want to ensure our team members are supported all the way.

Not everything we do works and that’s okay. We learn from those things. What is the least successful operations project you’ve contributed to and what did you learn? (No need to mention real names if it’s an issue)

At the early onset of COVID, I had initially expected things to go back to “normal” by Fall 2020 at the latest. At the time, we had rolled out initial policies consistent with CDC and local/state guidelines and altered the way we approached our work, which included all team members having to work from home indefinitely. This new approach to working presented initial challenges, amongst them caring for family members (or oneself) who got COVID, feelings of isolation working from home for an extended period of time, and addressing stressors as a result of work-life imbalance. I had not been in situations in the past where I can easily glean from experience what we can do to rectify these challenges because COVID was truly an unprecedented moment that even the most senior HR practitioners had trouble grappling with. What I ended up doing was prioritizing our need to be in compliance and not taking it a step further in advocating and supporting our team members in more meaningful and proactive ways.

It took this occurrence for me to believe that there is a moral imperative to create cultures and policies that support well-being in meaningful ways and can help team members thrive in their work and life. We do not stop being human when we log on or off from work. Life continues on. When serving team members of an organization in an HR capacity, you really get to experience the breadth of the human experience. And it is during these unprecedented moments where you can seize the opportunity to walk the walk ourselves as leaders, recognize the realities and struggles of life, and support team members by continually advocating and going above and beyond in this pursuit. We will not be perfect all the time, but if we remain committed to doing what is best for our team members, it can change business and our world for the better.

What’s been the most exciting part about joining Sidebench so far?

My first few months at Sidebench have been truly phenomenal. While onboarding, I have had the opportunity to better understand our mission, our team members, and the products we help build for our clients and it has been humbling to see the credible impact the products we build have on our end users. There is a vibrant energy that comes with working with such kind and talented people who care deeply about what we are doing, and I cannot imagine being anywhere else, but capturing the opportunity and the work that lies ahead.

We love to find people that ADD to our culture vs fit into our existing culture. What are some cultural aspects that you’ve experienced that you hope to bring with you?

Ensuring that team members are able to bring their full selves to work each and every day is something I bear in mind as I help lead People Operations here at Sidebench. This belief is ultimately rooted from my lived experience of attempting to fit into a place I thought I did not belong in. Having grown up first-generation and being the first in my family to graduate from college, these interwoven identities initially made me feel disadvantaged since I did not know the “right people” or have the “right network.” Although I can say it has worked out for me thus far, these identities of mine have kept me grounded. I want to ensure that we provide opportunities here at Sidebench for those from non-traditional backgrounds and afford them the same chance and give them a fair shake.

Describe your super power or describe what unique skill/perspective you bring to the team here.

Being in my role, it is incredibly important to master the art of conversation, and that ultimately comes down to being tactful enough to listen, confident enough to express your beliefs, and subtle enough to search for the reasons behind one’s thoughts.

I am also naturally a conscientious and perceptive person. When I combine these two personal traits with the need to converse with team members everyday, I am able to better understand what is going on within my organization and how to best show up for my team members. It goes without saying that I also look through the lens of humanity in everything I do and every decision I make. How I show up to work through the lens of humanity allows for my own intention and authenticity to shine through, and I believe that is incredibly valuable for loyalty, respect, and culture to be built. This is what I hope to bring to Sidebench!

Outside of work, what are you irrationally passionate about?

While I pride myself in always being people-centric and advocating for what is best for our team members, I do enjoy finding time for myself to decompress and watch movies while devouring a tub of movie-theater popcorn. (Fun Fact: it is no joke, I seriously LOVE popcorn, but only if it has been popped and doused in butter at the movie theater. Microwaveable popcorn is unacceptable!)

What skill, practice, behavior, hobby or habits are you currently working on?

I am currently keeping my streak alive on Duolingo by brushing up on my Spanish. Although I took three years of Spanish during high school, I lost much of what I learned in the years afterwards and would eventually like to be able to read, write, and speak Spanish again. (“Hoy por ti, mañana por mí.”)

Bonus Question: What book, publication, or podcast have you most recommended lately and why?

Recently, I have recommended Educated by Tara Westover. At the heart of this memoir is Tara herself, who was born in the mountains of Idaho and grew up isolated from mainstream society with her family. Education was never embedded as a core part of her upbringing and it was not until her brother got himself into college and came back with news of the world beyond the mountains where they grew up that Tara decided to go on a quest for knowledge that ultimately transforms her. I will try not to spoil too many details, but this novel is a universal coming-of-age story that gets to the heart of what an education is and what it offers: the perspective to see one’s life through new eyes, and the willingness to change it.

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