Employee Spotlight: Troy Kyles

In our Employee Spotlight series, we chat with a Pathrise team member each month about their career journey, expertise and experiences. This month, we’re excited to sit down with Career Mentor, educator and counselor, Troy Kyles.

About Troy

Full Name: Troy Kyles

Current Role: Career Mentor

Location: Philadelphia

Time at Pathrise: 1.5 years


The 411: what’s your role like, day-to-day? Break it down for us.

To help me stay energized while talking with people all day, I start my day at around 8 with a self-care routine. My routine starts with yoga to get my mind right.  After I make sure my wife is all set if she needs to go into the office, I plan out my day and get started on my daily tasks. At around 9, I prep for upcoming sessions, answer emails, and do any necessary follow up on previous sessions. My mornings also include high-level admin tasks, calls, and any other necessary communications. I take a little break in the afternoon before diving back into my work. Then I wrap up my day.

Sessions with fellows are a critical part of my day. Much of what we discuss in sessions with fellows depends on where the fellow is – for those who’ve been here a while, it’s ensuring they’re progressing with tasks like optimizing their resume and doing outreach. For newer fellows, it’s about getting them comfortable with the platform and other tools. Every day is different, depending on who I’m interacting with, but I try to keep a theme for certain fellows to make it easier to manage.

To keep myself motivated and engaged, I try to set a theme each week. For example, if I’ve been utilizing a specific job board or specific industry mentors have been impactful in helping certain tracks, I’ll share those or funnel opportunities to engage with them.

Can you elaborate on why you feel it’s important to do self-care and prioritize yourself first?

We have a diverse group of fellows, and when I’m pouring into so many people every day, I often have similar conversations but from different perspectives.

It’s crucial for me to prioritize self-care to avoid burnout. I follow a YouTuber who shares different yoga challenges to help avoid burnout–I make sure to do at least 20 to 30 minutes of yoga every day to recharge. Even a short yoga session is a great workout. It’s the perfect self-care activity when time is limited. Without self-care activities like yoga, I can sometimes feel antsy and have negative thoughts, which makes work seem more daunting. Starting the day with self-care makes me more productive and better able to support others.

2023 was a rough year and as a Career Mentor, you were on the forefront of helping fellows navigate a challenging market. What was one of your biggest fellow success stories last year?

I had a fellow whom I helped place on the last day of their fellowship. Literally, the very last day. But I trusted the relationship we built. I was confident she would maintain integrity and acknowledge that she got the role, instead of just leaving quietly on her last day. She was crying tears of joy because she landed a job at a self-driving AI company, something very futuristic! After we helped her negotiate her offer, she received a $10,000 sign-on bonus, her desired salary, and a remote role.

When I was helping her search for a job, she would often get far in the hiring process, but get rejected at the last round. with feedback like they had accepted an internal referral, culture fit, all those biases and isms. Many times, why people don’t get a role has nothing to do with the work they put in or I put in as a mentor. Sometimes despite all the preparation and support, the final decision isn’t in our control. Thankfully, I was able to draw from my Master’s in Counseling background to help students navigate their emotions and challenges. A lesson I’ve learned is that sometimes, you have to endure the cons to enjoy the pros.

Did you experience anything surprising or have to do anything different last year as a CM in order to help job seekers find employment, compared to previous years?

Coming out of the pandemic, motivation levels were low because the job market favored job seekers. But as society reopened, there was downsizing. Jobs were lost. Instead of telling fellows to focus solely on hard skills and skill-building, I emphasized soft skills like empathy. In a way, I became like a school counselor for my fellows, drawing on my counseling career experience. I didn’t expect to have to provide this level of support to adult job seekers in this capacity. I’d previously worked with adults who were returning citizens from prison or coming back to school later in life who were sometimes anxious about their job prospects. However, seeing people with more years of work experience than myself struggle to find jobs made me prioritize their well-being more. The same things I prioritize for myself I echo for the fellows, too. It’s such a collaborative environment and you develop strong connections after talking with people twice a month for so many months. You grow an affinity towards them and you can see their growth and achievements.

Your professional background is mostly in education of some sort – secondary, post secondary, career services, etc. What sparked your interest in the tech space?

While I enjoyed working in education, I experienced serious burn out.. There was always something that could change the trajectory of a school counselor’s job in the Philadelphia area . First, there were not a lot of people who looked like me in the role. A lot of people didn’t  know what a school counselor is supposed to do, meaning anything that an administrator didn’t want to do would be delegated to a school counselor. That wasn’t a good use of my skills.

When the pandemic hit, I was laid off.I started looking into remote work that was education-adjacent. I started working in enrollment for Howard University through a subsidiary company. From there, I worked at a tech bootcamp and it went up from there.

I really enjoy  my current role because it involves the same key skills I used as a counselor, but also empowers me to hold  fellows accountable and help them reach their goals.. Even exciting articles like this one and recognition from the team remind me that I’m still making a big impact.  I’m fortunate that I found a way to monetize my skills. No matter where I am or what project I’m working on, I can use my skills to make a positive impact.

Troy kyles

I noticed that your Masters is in Education and your degree is in Psychology. Do you feel like that foundation has helped you to better understand human behavior and connect with fellows, students, etc?

My favorite class in grad school was Group Dynamics–it not only taught me how to read a room, but also how to adapt without losing myself. Most people will say that I’m consistent. I’m going to be myself regardless of the space. My counseling background definitely helped me develop consistency, as well as the ability to stay calm in the midst of the storm. Looking for a job or any new thing you do can be stressful, scary, and exhausting. Thankfully, I can lean on the skills I learned in grad school to keep a cool head and push forward effectively.

While I come from a family of educators, all of them were teachers– I knew I didn’t want to grade papers! I decided to do my master’s program in my final semester in college from talking to my advisor, who was great. They set me up for success, understanding the broad range of perspectives I had from growing up in different areas, from the inner city to the suburbs to school in a rural area. There’s not too many groups of people I haven’t been around and that makes me a jack-of-all-trades.

At a time when Black male educators are so few, you also seem really intentional about making an impact through your work, particularly in communities of color. Can you shed some light on how this factors into your career trajectory?

People often say tht one of the most important things you can do is to get a trade, learn a skill, or be an entrepreneur. I think my trade is my identity and the spaces I choose to show up in. I know many schools that don’t have a male school counselor. And only 2% of educators are black males. I only have one other POC friend who’s a school counselor in the Philly area. Whenwe cross paths, we joke about how the schools are filled with educators who look like her. . But the men of color either run the school, clean it, or police it.

Representation is important to me. But I also don’t necessarily feel isolated in my experiences– that’s my superpower! Many of the people or youth who look like me or are described as having the same culture as me. I’ve found my voice as a professional amongst peers, people older than me, and younger than me. I was 23 as a school counselor, fresh out of grad school and most of my colleagues were much older than me. When I did career counseling, I was working with 18 to 26 year olds.It’s tough to be a young twenty-something managing a bunch of other young twenty-somethings. You’ve got to set boundaries because you don’t want to lose them.

You recently assumed a co-chair position for Pathrise’s Blackrise ERG and you’ve posted before about another BIPOC group that you’re a part of – The Man Cave. How has holding space with these groups impacted your professional journey?

I’m usually modest to a fault. My wife and my friends tell me that a lot! I’ve been trying to be more active on LinkedIn, celebrating holidays, interacting, and supporting others. These groups were some of my first steps to reach out and affect change in new places.  Blackrise’s mission aligns so well with my values and experiences, I’m excited to help make an impact there.

Like I mentioned, my mom is a teacher. Donating to the schools was a key part of our initiative this February for Black History Month. I’m actually bringing a bunch of school supplies Pathrise purchases to a school tomorrow–I’ll take a picture and ask the teachers to make a video with her class. I think it’s important for me to reach out to people who look like me in these spaces. It can get lonely or isolating sometimes without proper representation

Troy kyles

Students at Mary McLeod Bethune School in North Philly and their Pathrise-donated school supplies

Although I’m a counselor myself, before the Man Cave, I’d never been in any form of counseling or therapy in my life. I was always like, “I would never need to do that!” But the Man Cave group was the perfect life coaching program for me. It’s a group of dynamic brothers with lots to share.  I’ve been going Tuesdays for a year during my lunch break. I love it–the topics are so aligned with my experiences and values. It’s been instrumental in helping me connect with people and not feel like I’m overdoing it. While I personally know that I’m cool, smooth, funny, and fly… To others, I can still be modest to a fault. Sometimes I don’t advocate for myself or achievements enough.

The ManCave helps teach me strategies to stay, avoid burnout and manage fatigue. When I prioritize my needs, I don’t feel like I’m overexerting myself or burning myself out. After allI can’t be the best of anything unless I’m pouring into my cup. Because by the end of the day, I’m like, “sheesh, this was a day” – but that feeling isn’t heavy anymore.

As an aside, it seems like sometimes you see a lot of incendiary posts on LinkedIn, with people trying to get clicks or attention for their business. It’s a breath of fresh air to see someone celebrating others and themselves, too. 

People used to – and still do – go on LinkedIn when they need something. That’s not how the world works. If you only talk to a person when they want something, that’s not going to be a person in your life. Sometimes you have to “give one to get one”.I’m a firm believer in that. LinkedIn has been my only social media (I don’t have any other platform), but putting all my eggs in one basket has paid off. LinkedIn has been extremely helpful for my growth so far.

Lately, you’ve been pursuing scrum master certifications – is this in preparation for an upcoming pivot to Agile development? What sparked this desire to switch things up?

It was organic. I met a friend who’s a scrum master at Jefferson University Hospital and I was telling him how I was trying to get into project management. He asked if I’d ever heard of this very similar but newer and more innovative method. I shadowed him for a day and was so impressed–I’m having six or seven meetings a day, while he’s having six or seven meetings a week! And the impact was similar.. He told me he did a 90-day career accelerator.I earned that credential through him, then started studying for PSM. I knew I was on the right track because I only failed one one point when I took the test the first time. When I took the test again, I got a 90% and now I’m studying for another.

I want to start doing project management on a contract or consultant basis, since I have  so many skills transferable to project management. For example,  soft skills like being able to talk to different people, hold people accountable, and lead by holding space. Project managers don’t necessarily have to know anything about the software they’re developing. They can hold people who are developing accountable and share their wins and losses.

I know we have quite a few fellows who are trying to navigate pivots in our program. What are one or two things you would recommend to someone if they’re trying to pivot in their career?

Network, and make sure you’re networking upwards. What do people know you for? With my friend, we built a connection through education. When he made the pivot, he told me he knew I would be good at it because I’d been doing it. Find mentors, allies, and peers that can take you with them. It’s continuous improvement. Don’t get a cert and then not apply. It’s got to be something you do at least a few times a week or month. Occasionally, I’ll take old practice exams to make sure I remember the terminology. You use it or lose it.

For me, those are the two things: network in a way where it’s a reciprocal relationship and also continuous learning. If you just settle, you’re going to get the short end of the stick every time.

What do you envision as your ideal project management role?

I’m excited by any project manager role as long as it has a mission that I can support. Anything in education, Ed Tech, or community impact. With an agile framework and Scrum, it’s people over processes. At Pathrise, we have so many different processes, but they’re all still aligned and it’s people first. When I was studying for the exam, it felt like I was reading my own version of a book. I think in analogies and it helps things like land home. Again, there’s not a lot of black men in the field – I was on the hunt on LinkedIn trying to find people who look like me and only seeing like my friend and a couple other people. Scarcity is what I’m leaning into. I’m excited to bring my unique skills and experiences to a project manager role where I can continue to make an impact.

Learn more about Pathrise’s amazing employees featured in our monthly spotlights!

Ben Hyland

Kelly Barber

Niema Majidimehr

Daphne Ellis

Maurcus Dunson

Ash Ayvar


Evelyn Kwong

With a background in HR and events, Evelyn blends her knack for writing with her passion for seeing people succeed. She and her rescue dog Darby live in sunny Long Beach, CA

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