Mi Historia Interviews - Pamela Michelle Rosario Pérez on Adaptability
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Mi Historia Interviews - Pamela Michelle Rosario Pérez on Adaptability


Pamela is an award-winning business leader in the areas of customer experience strategy, diversity & inclusion within the high tech industry. Her commitment to bridging the gap between the innovation economy and historically marginalized communities led her to launch initiatives such as the CyberWarrior Academy, Massachusetts' first certified cybersecurity and machine learning apprenticeship for women, veterans, and people of color. This, together with her passion for real estate investing led her to found Rocena Real Estate Strategies, an investment firm that teaches Black and Latinx youth how to build wealth through real estate and offers scholarships to high school students looking to drive change in their communities. She also serves on the board of Artisan’s Asylum, a nonprofit maker space in the greater Boston area. Her accolades include: El Mundo's 30 under 30 Most Influential Latino Leaders Award, Hubspot's L4 Services Award, and Chica Project's Mentor of the Year Award. Her unconventional upbringing and immigration story are covered inThe Formula: Unlocking the Secrets to Raising Highly Successful Childrenby Harvard economist Ronald Ferguson and award-winning journalist Tatsha Robertson. Today, you can find Pamela having a blast traveling the world in her role as Rapid7's Program Manager of Customer Experience Strategy.


/ What is your name? Do you know the story behind your name?


My name is Pamela Michelle Rosario Pérez. My paternal grandmother loved the name "Michelle" so much that she campaigned to include it in my birth certificate. Even though my first name is "Pamela," my family and close friends call me "Michelle" to this day. 🙏


/ How do you self-identify your race and ethnicity?


I identify as Dominican, Afro-Latina or Afro-Taina. I am immensely proud of my Caribbean and African roots. 🇩🇴


/ Do you identify with the term Latinx? Do you call yourself Hispanic?


I identify with the term Latina more than Latinx or Hispanic. That said, I recognize the appeal and value of Latinx. I appreciate that it is gender-neutral and inclusive of those who identify as agender, trans, queer, non-binary, gender-fluid, or gender non-conforming✊.


On the other hand, I am less of a fan of the term Hispanic. Although it remarks on the tongue that unites a great number of Latin Americans, it erases the many other languages, native and otherwise, that our people speak. South America and the Caribbean are linguistically diverse areas with over 400 spoken languages. Hispanic doesn’t make room for Haitian Creole, Quechua, Papiamentu or othersin my opinion, it’s overly simplistic.


I, personally, identify as Latina. I like highlighting the “a” at the end of Latin because my lived experiences have been those of a woman 👩. Many of the obstacles I have faced in my life have been due to my gender and society’s perception of what my role should be. And although we’ve accomplished great things over the last few decades, there is a lot of work that remains to balance the scales ⚖️ in the workplace and society as a whole. I am proud to speak out on the gender-based injustices that plague our society, and for me that starts with sharing my experiences as a Latina 👩‍🦱.


/ Share with us more about your upbringing. Where were you born? Where did you grow up?


I was born in the Dominican Republic. Although I was born in the capital, I spent many years in a small town called Sonador in the Cibao region. Sonador es mi campo. I moved to Miami, Florida when I was six, 🏖️ and then I moved to South Jersey as a teenager.


I am the oldest of twelve siblings and come from a hard-working, tight-knit immigrant family. We moved a lot in search of better job prospects. After graduating high school, I wanted to embark on my own search for better opportunities, so I moved to Cambridge, MA to attend university and fell in love with the city of Boston. I hate the winter weather, ❄️ but I love my friends and professional network 👭.


/ What did you want to be when you were a child? What were your career aspirations and why?


I wasn’t exposed to much when I was younger. My dream was to be a flight attendant because I thought it was the only way a woman could travel the world 👩‍✈. My plan B was to become a receptionist so that I could wear a suit, work in a fancy office, and pick up the phone. I loved being on the phone. I thought it was so posh.


/ Let’s start with your K-12 experience. Tell us about the schools you went to, and how did they help you prepare for a job or career?


In the Dominican Republic, I went to small, local schools. In Miami, I went to a public language magnet school where a significant portion of my education was in French. I continued attending public schools until I graduated high school.


I do not think school prepared me for a job, but I credit it for exposing me to different lifestyles and career options. I also credit it for exposing me to different people, because it forced me out of my comfort zone 👫. Growing up, I was mainly surrounded by Latinos who were part of our Christian community ⛪, so school is where I learned to engage and collaborate with folks of diverse backgrounds. School also opened my eyes to the fact people could turn their passions into lucrative careers, regardless of their race, immigration status or genderand for that I’m grateful✊.


/ Was the plan to always go to college? How did you choose which college you wanted to go? If you didn’t go to college, why? Did college help you prepare for a job?


I decided I wanted to go to college during my senior year of high school. As the oldest of twelve siblings, I had a lot of home responsibilities, so I longed for a chance to pursue my academic endeavors without needing to balance multiple obligations. Besides teachers, I did not know many college graduates. I was not sure I’d make it, but I wanted to give it a shot.


Due to my family’s financial situation, paying tuition was not an option and neither was taking out loans. A friend told me about ivy league schools, luckily. Once I became aware of their generous financial aid packages, I mailed in my applications to two schools. I was fortunate to receive a full-ride scholarship from both, and ultimately decided to attend Harvard University 💯.


/ Do you think choosing a college is like choosing an employer?


I’d say it is similar, but not the same. I chose a college that eliminated my financial barriers, and that was my main criterion. Choosing my first job was difficult. I was very involved in school clubs and other initiatives my senior year, but had not begun job-huntingI had no idea I had to! I remember people around me preparing anxiously for interviews with consulting firms and big banks. The suits, the mental number-crunching, the stockings, the study groups. I remember it all, but had no idea how or why it was happening. Nobody had spoken to me about the best way to prepare for post-graduation employment, so I was very lost🤷.


Auspiciously, a lawyer with political aspirations attended an event I hosted and asked me to become his Campaign Manager for a City Council run. I was scared and rejected the offer at first. That quickly changed once I got to know him and his platform. I could not say no to someone with a huge heart and a genuine desire to improve his community, so I signed on and brought a few friends of mine along. It was a wild ride🎢. We made mistakes, learned quickly, laughed often, got rained on, spoke from the heart, leaned in, and led with authenticity. His win led to him becoming the first Latino Vice Mayor in the city’s history. I stayed on as his Legislative Aide to execute on our campaign goal of bridging the gap between the historically disenfranchised and the innovation economy✊.


/ Did you do internships, apprenticeships, college campus jobs while in school to gain experience? Was it difficult balancing academics and extracurriculars?


Absolutely, I did it all. I was coming from a place where many of these opportunities only existed in movies; therefore, as soon as I arrived on campus I joined the outdoor club, psychology labs, a few religious and cultural organizations, and even an acapella group 👏. While my tuition was covered, I still needed money for living essentials, so I worked three jobs throughout my college tenure. My summer internships ranged from teaching child refugees in Dorchester to engaging in diplomacy and crisis response work in the Dominican Republic after the 2010 Haiti earthquake. It was challenging to balance academics and extracurriculars, especially around exam periods, but I deeply loved how I was investing my time. It was worth it.


/ What scared you the most about choosing an employer?


Not making enough to survive in Boston scared me the most. I considered pursuing a PhD early in my career. This meant I had to complete 1-3 years of additional lab work before applying to the neuroscience program I had in mind. The pay for these positions was less than $30,000 and I had no family I could stay with to help offset costs. The low salaries I was up against caused me to worry about being unable to pay living expenses in Boston/Cambridge 😔.


/ What did you wish you had to support you in the job search process? What resources did you feel were missing?


As a first-generation college student, I did not enter school with a strategic plan or the know-how to navigate it successfully. I was just trying to survive, give back to the ‘hood, and build my community. Since I did not see people who looked like me represented in the student cohorts applying for Finance, Investment Banking, and Consulting jobs, I did not think to apply. I was not sure that I had a place in that world.


For many first-generation students, preparing for post-graduation employment is a frustrating and confusing process. Imagine dedicating time to that while balancing a thesis, on-campus jobs, club responsibilities, and school work. Many of us don’t know where to begin. I wish there was a department dedicated to meeting the needs of first-gen students. I wish we had a team of people committed to having these conversations early, connecting us with business leaders who share a similar background and demystifying lucrative industries (i.e. real estate, banking, accounting, technology, etc) 😓😓.


/ How did being Latinx impact your job search? The career fair? The application process? The interview?


My background and lived experiences have definitely given me an advantage in the workplace. As an immigrant, I have had to figure out many things on my own or with little help. Early on, my grandmother taught me that if I wanted to accomplish anything in life, I would have to hustle, commit, pursue goals fearlessly, and use my brain to think outside the box. She always reminded me of the Bible verse Philippians 4:13. It is a mindset I carry to this day 👼.


Graduating from Harvard does not automatically translate into job security and a stable life. I was homeless right after college 🤯. I have had to pivot and leave unhealthy work environments. The struggles are never-ending. Nevertheless, my grandmother taught me how to advocate for myself, and my lived experiences have taught me how to turn my struggles into strengths. Being adaptable is my secret weapon 🦸.


When it comes to cybersecurity and artificial intelligence, many professionals know enough to be dangerous, but they do not know it all. We are still very much in uncharted waters. That’s exciting! A multitude of unanswered questions means that there is room for people who are curious, creative, and bold to take up space. In cybersecurity, your diversity is your advantage 💻. I appreciate how my company brings people of different backgrounds together and allows us to use our talents to tackle these challenges head on. I love thinking strategically, collaborating with cross-functional teams, and innovating. I like change. I enjoy spicing things up and making life easier for employees and customers alike. I often feel like my upbringing was the perfect training camp for working in the high-tech industry.


All of my life I have had to fight, nothing has come easy. That level of hustle is a great asset to employers.


/ Is Diversity, Equity, and Inclusion important for you? What does it even mean in your own words? How do you know if a company is checking the box or if they actually care?


Extremely important. I have left companies that I feel talk the talk, but do not walk the walk. Driving diversity, equity, and inclusion is no easy task. It requires a lot of hard work and dedication to seeing things through. Pushing for a more equitable society requires intentional action every single day 💯.


For me, diversity is about fostering environments of people with different perspectives, different lived experiences, different problem-solving approaches. Inclusion is about ensuring that everyone, especially those who have been historically marginalized, feels seen and appreciated for what they bring to the table. Inclusion is when your differences are genuinely perceived as a value-add to the company, when they’re part of the reason you’re considered essential. In my opinion, equity is what we achieve when we ensure systems, practices, and processes are just, while recognizing that there are no one-size-fits-all solutions. To me, equity speaks to ensuring everyone has equal access to a better future. Equity is having equal opportunity to make your dreams come true.


Diversity, equity, and inclusion (DEI) are not “nice-to-haves,” they are “must-haves”⁠—especially in tech. Internet users and malicious hackers come in all shapes and sizes. For this reason, it is vital that the workforce reflect the diversity of the ecosystem 💯.


/ What would you like to bring to the forefront regarding the conversation about Latinos in the workplace? What do you think is the important element of this conversation that is not talked about as much?


The concept of Cultural Assets versus Cultural Barriers is something I want to bring to the forefront.


Asset: 📋


  • Bilingualism/Multilingualism: Some English-language learners see their accents as a cultural barrier when in reality, bilingualism (or multilingualism) is a tremendous cultural asset. Speaking multiple languages can open doors into new markets and business opportunities. In addition, research has shown multilingual people display cognitive advantages in the areas of memory and attention. Be proud of this skill!


Barrier: 📋


  • Communication style: We use a direct communication style with a hint of sarcasm in my family. Throughout my professional career, I have learned that this style resonates with some people, but it can cause confusion and serious misunderstandings with others. On one occasion, I was leading a project that hit a wall due to a breakdown in collaboration. At first I took it personally. Soon, however, I learned that the issue was the communication style I was using to guide the project along. I had never heard of multiple communication styles, so I was quick to research it. This experience humbled me because I thought my “directness” was a cultural asset, when it was instead causing unintended friction when engaging with people of diverse backgrounds⁠—it was a cultural barrier! As we navigate the workplace, it is important to be conscious of how certain cultural practices can negatively impact well-intentioned efforts. Do not shy away from assessing your work style. Self-reflection is essential to growth.