Joshua Encarnacion (Bay Area, California)

Career: Chief Learning Officer at Outco Inc, which is a company focused on helping software engineers (computer science college grads, coding boot camp grads, and mid-senior level career software engineers) earn their next job.

As CLO, I’m responsible for aligning our people development efforts (training & coaching services), market strategy (connecting with new customers, recruiters, and partner companies) and our team goals with business growth.

1- How did you become a professional in your current field? 

To become a professional in my field, I was very intentional about my fields of study in college. While attending the University of Massachusetts – Dartmouth, I studied general engineering for 2 years, human resources management for 2 years, and did a minor in Leadership and Civic Engagement.

To earn some cash and keep myself busy with more learning, I did jobs like a tour guide, orientation leader, and residents assistant when I wasn’t studying, which all taught me valuable skills in training, coaching, and running a team.

With my college experiences, I was able to earn a job working for Google right after college. At Google I developed my passion for helping technical-minded folks (mostly software engineers), learn how to develop emotional intelligence & people skills better… outside of the tech industry. Many people believe being a software engineer is the only option, but those in the tech industry know you can work in tech in many different roles and professions, like recruiting, finance, marketing, legal, and in my case, training. I was a technical recruiter for Google and ran training classes on presentation skills, leadership & management skills, meditation, and mindfulness practices.

After Google, I went on to build 3 different startup companies (hiring and training thousands of technical and non-technical professionals) and also worked at Uber for a while to support the build of an iOS training boot camp.

Taking all I learned in college, and not being afraid to test it out in the “real world,” allowed me to grow really comfortable and confident in my skills as a training professional. It took A LOT of support from friends, family, and MANY mentors (no one makes it alone), but as the years passed and different challenges arose, I didn’t quit and made sure to keep close to the people who believe in me WHILE paying it forward and believing in others who was trying their best to become a professional in their field.

2- What is a quality that makes you successful in your career?

My ability to communicate effectively makes me successful in my career. 7 billion + people on planet Earth (someone check my math, lol) means 7 billion + ways to think about how to get ideas out of your head and into somebody (anybody) else’s head. All-day long we are exchanging ideas – whether it be in the classroom, at home with fam, or in the workplace it never ends. Those who can clearly & precisely get their point across, in a way where others FULLY understand them AND want to support the idea, will always find their way to success. Best part! Success is often defined by the most precise communicator in the room because people listen to that person, which makes them a leader.

In the “real world,” it gets VERY challenging to communicate. ESPECIALLY when we take into account different backgrounds, races, genders, goals, ambitions, educations, religions, needs, wants, etc. / Everyone comes with a story, being able to put the stories aside long enough to exchange ideas and information (communicate), allows 2, and many folks work together.

In my experience, being a proud Afro-Latin, first-generation Dominican-American man, born into poverty and navigating many survival driven environments, I’ve had to work EXTREMELY hard to be understood and communicate my ideas in a way the folks around me understood. Especially in spaces where I am the only one of my origins, background, make-up, etc. Common story for us professionals of color in the tech industry. At times, not fair, and it makes me feel uneasy because the dominant society is often in the wrong for letting their bias and insecurities paint me in the false light, which we will all work on continuing to overcome together. BUT my responsibility to move forward towards what I define as success using the qualities which carry me through – in my case, effective communication (storytelling, writing, presenting, public speaking, running meetings, facilitating trainings, explaining ideas, selling, marketing, being able to hold engaging conversation for hours at a time, and being open to sharing with AND learning from people of ALL different backgrounds and experiences).

Communication amongst people (especially when considering all of our differences) isn’t easy. But I wholeheartedly believe in further developing the skill and using every minute I’m breathing as an opportunity to better practice understanding another and using my words to be better understood.

3- What 3 tips would you give someone struggling to reach their goals?

1. Read books written by people who have achieved the goals you want to achieve. A lot of the knowledge and information we need to succeed in achieving our goals has been made available in books, and if you can’t find a book that speaks to you, use Google search to find articles! Just make sure you double/triple check the author’s background to make sure they are a credible source.

2. Ask every question on your mind, so long as it doesn’t involve intentionally hurting someone else, and never mind how you are perceived. Those who are proactively curious will find answers to their challenges A LOT faster than those who fear being perceived as ignorant or unaware. We often fear asking questions because we believe people won’t be willing to help us, but the majority of folks love helping others because it makes them feel valuable (which is why I’m sharing these insights so willingly). For those who negatively react to your questions/don’t help, thank them for their time and find another person to ask your question.

3. For anyone with goals (periodt), prioritize your health above everything else. For me, this means eating well, sleeping well, hanging out / keeping up with friends & fam, journaling about my day and feelings, checking in with my therapist every so often, dancing, laughing, cooking, and finding different ways to destress.

4- Name the top 3 goals you achieved?

1. I helped endow a scholarship during my time at UMass Dartmouth. Working with a team of 6 seniors, we fundraised $76k and invested a majority of the money in creating the “DREAM Scholarship,” awards $1,000 every year (for forever), to a student with a Dream in dedication to the service of others. Feels good to be able to pay it foreword with sharing knowledge AND providing funds

2. Helping build Outco Inc. When I joined the company, we were 4 teammates and barely had 15 customers, now we have ~20 employees, and have helped 1,500+ software engineers earn jobs with an average salary of ~$110,000 / year. Having built a lot of the social, emotional, and behavioral training curriculum myself (courses on confidence, communication skills, presentation skills, interviewing, and more) it feels good to validate your ideas and be part of a team which wins by helping others grow the skills necessary to get what they want, which in their case is a job.

3. Staying close with my family and friends over all these years of accomplishment. Nothing is harder than balancing personal life and career aspirations. Some of the challenges most ambitious folks never really speak on are ones we often struggle with alone – missing birthdays, missing family cookouts, being far away from “home” for long periods of time, and growing/changing into someone who no is longer interested in doing what they used to do in the past OR what most of their loved ones do now. It isn’t easy to accept all the changes that come with being dedicated to your goals, and often, the first thing I see many ambitious folks do is forgetting about their community – friends, and fam. I’m very proud of my efforts to stay grounded, connected and present with a good number of folks who raised me and helped me become the person I am today.

YOU KNOW WHO YOU ARE, LOVE YALL! #WeJustGettingStarted #Flourish

5- What inspired you to reach your goals?

The grit, resilience, and perseverance demonstrated by my first coach, teacher, and support system, my Mom. She had me at 16 years old, and at the time, we lived in project housing with minimal support from my father (who was deported to the Dominican Republic a couple of years after I was born).

She didn’t let her circumstances OR environment, determine the life we would be living, and due to her example, I feel as if any/all goals I set for myself, or m team(s) set together will always be achievable if we remain focused, committed, and flexible in HOW we get where we are going.

Our family had significant ups and downs, and nothing about our survivor story was pretty. But with persistence (and probably many lucky breaks & community support), I watched Rosemary Hernandez (my mother) pull us from a harsh reality, to what we believed to be a dream come true. 13 years after I was born, my Mom had secured two master’s degrees (MBA & child psychology) and moved my younger sister and me into our first house. What more inspiration do I need?

Thank you, Mom – I love you!

6- How did you overcome obstacles to reaching your goals?

– Mindfulness meditation

– Taking responsibility for my actions

– Being coachable and learning from mentors

– Therapy

– Exercise

– Asking for help from friends and fam

– Reading (an hour a day)

– Never quitting on my goals, but being flexible with my approach to goals

– Studying positive psychology

– Idolizing truth and honesty OVER everything else

– Being very clear on who I am, my passions, my interest, my desires, and most importantly, my goals

– Always believing I’ll reach my goals and continuously repeating back to my self, “It’s a matter of when not if.”

– Not being ashamed to ask questions or look “stupid.”

– Staying young aka dancing, laughing, having fun, and enjoy life

– Celebrating the best parts of my culture, my people, my community, which is the best form of loving myself and the people around me

– Always being open to feedback and pushing myself to continue learning

7- How do you keep your inspiration from decreasing?

I remind myself, daily:

“Life is short, and we will all pass one day. My job in life is to do what I believe in my heart to be the most useful thing I can do to help myself and the people around me that, and love deep.”

Find Josh on Twitter @joshuaenc and visit him at his place employment at