Employee Spotlight: Ben Hyland

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 Ben Hyland, Pathrise’s Learning & Development Specialist on the Career Team.

About Ben

Full Name: Ben Hyland

Current Role: Learning & Development Specialist, Career

Location: Florida

Time at Pathrise: 4 years

Website: https://www.benhylandlives.com/


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

A good chunk of my day is spent  on quality assurance, specifically ensuring fellows are application-ready. Most of this quality assurance work centers around resumes– making sure fellows’ resumes align with their qualifications and career goals. I also help review LinkedIn profiles, support with cold outreach strategies, and in general assist with troubleshooting fellows who get blocked in their job search.

Besides quality assurance, I manage L&D [Learning & Development] projects, which includes resource development. For example, in Q4 2022 the team raised a need for better supporting our visa-holding fellows, so I dove deep into the subject and created resources to fill the gap. Not only do I provide ongoing L&D training for the team, but I also coordinate a team of trainers comprised of Career Mentors, Career Leads, and our Chief of Staff, who assist in training new career mentors. We constantly keep the team’s Resource Center fresh by updating policies and procedures, creating a smooth onboarding process for new team members.

We’re working on a fellow-facing curriculum that will hopefully come out soon. Additionally, at any given time, I mentor 10 to 15 fellows.

You’ve been in the career coaching space for years now. Tell us more about your journey into it.

It’s been quite a journey; this is my third career change. I spent five years in property management, followed by three years as a visiting assistant professor. During the last semester of my last teaching contract, I taught a professional writing course, which I transformed into a career development course. I’ve always had a passion for career coaching, even during my time in property management, especially during the Great Recession. I assisted residents in polishing their resumes to help them find new work and avoid apartment turnover due to evictions.

After I turned my writing course into a career development course, I knew I had to focus on career coaching – and it’s been a lot of fun! I love helping people. So I transitioned from teaching in higher ed to being a career coach. Then I came to Pathrise.

What made you join Pathrise in the first place?

I joined Pathrise in August 2020. he big kick in the pants for a lot of us was the pandemic. My wife had been working from home for yearse but we had worked together in person many years ago. I always wanted to be her office buddy again, working from home with her.  I was also tired of the grind of higher ed. There was so much bureaucracy. I wanted to work somewhere that was more streamlined, mission-driven, and offered growth opportunities, both professionally and financially. Pathrise checked all those boxes.I joined without hesitation.

Seeing Pathrise grow over four years, what has that experience been like?

Seeing Pathrise grow had been a wild ride in all the best ways. I love being here at Pathrise. When I started,  the team was very small. There’s been many turns in the road since then as our team has grown tremendously. Reflecting on this question, I believe we had many of the right answers early on. But we lacked the resources or capacity to implement them fully. Over the past few years, however, I’ve seen significant progress.

It’s a rush working at a startup. My previous five-year stint in property management was with a well-established group flush with cash.  And while rewarding, my work in higher education settings lacked focus and professional growth opportunities. Pathrise has been great. I’ve loved helping to build the company and seeing it grow over many years. I’ve never had that sensation before.

2021 Offsite at Lake Tahoe

What prompted your pivot to learning and development?

It happened naturally, but timing was critical. When I started working at Pathrise three and a half years ago, my focus was doing a great job in my career mentor role. Other opportunities, however, quickly presented themselves. Through exploring these opportunities, I recognized we lacked an effective onboarding training program– and we desperately needed one. Without a clear onboarding program, our existing approach felt a bit like a trial by fire. So I took it upon myself to improve our onboarding. Drawing from my background in teaching and coaching, I was able to clearly see what was needed to scaffold training so that people would be successful. Now, the program continues to grow and evolve about every six months.

As I was working on our onboarding, resource development became another significant responsibility. Managing both onboarding training and resource development became extremely demanding. Eventually, all these efforts came to a head and a more focused L&D opportunity arose. I stepped into a Learning and Development role where I could have an even bigger impact while working on similar projects  Timing played a role, the  pivot was mostly to meed our need for L&D as a business. I received a lot of support from leadership throughout this process.

I’ve spoken with people who wanted to transition into L&D but didn’t know how. What are some things you’d recommend?

Many formal pathways exist for entering the L&D field, including numerous certifications and dedicated college programs. Instructional design training can also be beneficial. However, my journey into L&D was more unconventional. What worked best for me was to first follow my passion and then entrench myself in an industry, specifically the career coaching space. It helps to really enjoy teaching if you’re in L&D. Interestingly, my wife and two additional close friends who were already  working in L&D–They also took very unconventional career paths to L&D. They achieved success by excelling in their respective industries and embracing opportunities for growth.

How do you balance your writing career with your work at Pathrise?

The most important thing to keep in mind is “What is a career?” To me, writing is not a career because where I’m at now, it doesn’t pay the bills. A career pays the bills. When I get that paycheck, it funds the fun – and creative writing, which is part of that fun.

Pathrise fuels three of my major passions: helping others, teaching, and engaging in professional writing. These energize me and contribute to my overall fulfillment. Pursuing my MFA in creative writing was a personal endeavor,I did it  for my own growth and enjoyment while working full-time in property management. When I finished my MFA, I transitioned into being a professor. Balance for me, at this phase of my life, includes my writing group. We meet virtually every two to three weeks and that acts as my accountability mechanism, to always be in that creative mindset. This creative outlet not only fuels my energy at Pathrise but also enhances my overall quality of life. It all works together in many ways.

I don’t put a lot of pressure on myself for creative stuff, apart from the bi-weekly writing group. I think the goal naturally presents itself. That’s how my most recent book came around.

Do you have any big projects or announcements on the horizon?

Shelter in Place – by Ben Hyland

2022 is when my book came out. It was awesome! In terms of new projects, right now, I’m just writing. Once I amass enough quality poems to fill a manuscript, then I might consider doing another book. In the meantime, I would love to do a collaboration with a visual artist because I have poems that would look better on a wall than in a book. If someone else is inspired and there’s a collaborative element where they draw or paint and I can react to that – I’ve never tried that before.

As for personal announcements, my wife and I are hitting five years of marriage in December!

Do you have a favorite poet?

Yeah, but it always changes. There’s my favorite poet of the moment, and there’s a poet that I really want to get into. My favorite poet at the moment is Joel Dias-Porter. He’s a legend among poets. He’s amazing. And he just had his first collection come out last summer. This was like the album drop of the century for me and everyone who knows him was so looking forward to this. Joel’s book is called Ideas of Improvisation. I cannot recommend it enough. It’s brilliant. So he’s my number one at the moment and then the person that I’m really looking forward to diving into is in my shopping cart on Amazon: Kweku Abimbola, Saltwater Demands a Psalm. That book received the 2022 Academy of American Poets First Book Award. Really good stuff.

What’s next for you? Career or otherwise?

Career-wise, I bleed purple. It’s been a wild ride, but I’ve enjoyed every minute of it. And I love my role at Pathrise. I’m so excited to continue my journey at Pathrise and see where it takes me nexte. Outside of my career, my wife and I took a Mediterranean cruise last fall. We don’t have a travel bug per se, but if we can swing doing one big trip every year, it would be really awesome. This year, we want to try this Costco travel package where we go from Amsterdam to Paris to London. It’s surprisingly ! We definitely want to see the Pacific Northwest next summer as well.

(Continued below)

Ben and his wife, Maggie

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

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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