Greenhouse

Hiring doesn’t have to be broken—and Greenhouse is out to prove it.

On this episode of Culture Uncovered, Jena chats with Will Leahy, VP of People at Greenhouse, a tech company redefining how the world hires. From remote culture done right to thoughtful candidate experiences and career pivots that actually work, this episode is full of gold for job seekers and culture builders alike.

What you’ll learn:

• How Greenhouse is more than an applicant tracking system—it's a candidate experience platform
• Why clarity is kindness in the hiring process
• Remote culture tips: team offsites, ERGs (called Arbors), and tools like Donut & Bonusly
• How Will’s career pivoted from recruiter to VP (and the one time a plane ride got him a job)
• The perks of "pleasant persistence" and proximity when job searching
  
  

Some Greenhouse highlights:

 📍 Founded - 2012
 👥 750 employees
 🌎 Fully remote with hubs in NYC and Dublin
 ✈️ Global Passport Program: work from anywhere in the world for up to 60 days
 🌱 Company values: Belonging, Purpose, and Entrepreneurship
 🔥 Strong performance culture with equitable recognition
 🚀 Yes—they are hiring!

To learn more about Greenhouse:

🔗 Greenhouse Careers Page
🔗 Greenhouse on LinkedIn
🔗 Will Leahy on LinkedIn

Transcript

Jena Dunay: Hello friends and welcome back to another episode of Culture Uncovered! I’m super excited to be here with my guest today. One, because I'm very familiar with this product. It’s very much part of the candidate experience, and you may have heard of it. It’s an applicant tracking system, Greenhouse! I’m here today with the VP of People, Will Leahy. So excited to have you here, Will! Welcome to the podcast. Tell us a little bit about Greenhouse. What does Greenhouse do?

Will Leahy: First off, I’m hyped because you’re hyped. That was such a good intro. Let’s go! My name is Will Leahy. I’ve worked at Greenhouse for about two years. I lead the People Success team. That includes our HR business partners, people experience and culture, development, performance, engagement, and IDEA, which stands for inclusion, diversity, equity, and allyship. Essentially, I wake up thinking about how to make Greenhouse the best stop in someone’s career. That’s our day-to-day focus, and it’s a lot of fun. I’m clearly bought in. I’ve got the Greenhouse book behind me and a green door! Didn’t wear a green shirt today... might need a costume change. Also, I’ve got two toddlers, a puppy, and I’m based in San Diego.

Jena: You planned that! Puppies are hard. I actually think our dog was harder to sleep train than my children!

Will: I’m telling you, two toddlers and a puppy? I’m going to write a book titled “Hey, Maybe Don’t.” But it’s awesome. A huge joy.

Jena: I love it! So tell us about Greenhouse for people who aren’t familiar or who aren’t HR tech nerds like me.

Will: Most people call Greenhouse an applicant tracking system, but I think of it more as a candidate experience platform. On the recruiter side, it helps organize candidate pipelines and ensures people have a great hiring experience. On the candidate side, we want applying for jobs to feel easy and human. No 37 fields to copy-paste your resume into. We ask for pronunciation, try to make people feel seen and heard. We want to be the opposite of the “black hole” job portal.

Jena: It is not fun! I’ve personally experienced Greenhouse as a candidate and it was way better than other platforms. If a company uses Greenhouse, I feel like it already says something positive about their approach.

Will: Totally. When I was at LinkedIn, Greenhouse was just coming on the scene. One of our solution architects said it was the best. I’ve had it in my mind to work here for a long time. We even track candidate ghosting and have tools to help prevent it. Our mission is to make every company great at hiring. That’s big, but it’s what gets us out of bed in the morning.

Jena: I want to circle back to how you landed at Greenhouse, but first, let’s hit some lightning round info. How big is the company now?

Will: We’re around 750 employees. Small but mighty.

Jena: And you’re fully remote?

Will: Yes. We have hubs in New York and Dublin, but we’re a distributed company. We also offer a Global Passport Program, where employees can work from anywhere in the world for 60 days. It’s amazing. People are everywhere, and that flexibility is priceless. It’s not without challenges, but we’ve leaned into making it work.

Jena: I think that’s a competitive advantage. What are some things you do to maintain culture in a remote environment?

Will: It starts with intentionally redistributing our real estate budget into connection. We support large company gatherings, smaller team offsites. Teams have gone to Cancun and Austin. We also support local meetups like “Table for 10” dinners. We involve people in customer events based on geography. On the tech side, we use tools like Donut to create random coffee chats, Slack channels for interests, and we’re intentional with onboarding. We have ERGs, which we call Arbors. We even flew our Arbor leaders to San Francisco for an offsite. It’s messy and not always perfect, but we try things, see what works, and keep evolving.

Jena: I love that! Let’s go back to your story. You mentioned you had Greenhouse on your radar for a long time. How did you actually land there?

Will: It’s been a journey. I entered the job market during the 2008 financial crisis. It was rough. My car broke down on the way to a job interview. I ran the rest of the way, sweating, but landed the job. I started out doing cold-call recruiting in a cubicle with a mirror that said “Smile and dial.” That experience showed me what I didn’t want, but also helped me find what brings me joy.

I went to grad school at Northwestern for learning and organizational change, then joined LinkedIn. I helped oil and gas clients implement LinkedIn Recruiter. That’s when I learned about ATS platforms like Greenhouse. I transitioned into L&D, then worked at Hulu, Virgin Orbit (yes, rocket scientists), and GoDaddy. Eventually, I met the Chief People Officer at Greenhouse at a conference. Within a month, I was in. Full circle moment.

Jena: That’s amazing! So many key takeaways there. Hustle, showing up, saying yes to new opportunities, even filling in when someone’s sick. You really carved your path. So many job seekers ask how to pivot, and your story shows how internal projects can lead to new lanes.

Will: Absolutely! Be vocal about what you want, be patient, and stay ready. You never know when a sticky note on a manager’s desk might say “Hire this person!”

Jena: Yes! And proximity. Talking to people, looking up from your phone, taking opportunities. It matters. Let’s pivot back into Greenhouse. What are some standout benefits or cultural features?

Will: Besides being remote with flexibility, we focus on belonging, purpose, and entrepreneurship. Those are our three core values. Our Arbors are key to fostering belonging. Purpose comes from our mission to improve hiring everywhere. Entrepreneurship is about trying new things, iterating, and sharing what works. We have the structure of a scaled company but keep that spirit of innovation.

We also reward high performance and have a transparent performance review and comp process. The Global Passport program is a hit. It’s all about treating people like adults and letting them work where and how they thrive.

Jena: I also love your careers page! It explains the interview process in detail. That transparency helps people feel more confident and informed.

Will: Yes! Clarity is kindness. Interviews are stressful. The more people know what to expect, the better the experience. We use our own product, and our bar is high. We want to be the best example of great hiring.

Jena: Let’s talk retention. How are you keeping people engaged and staying long-term?

Will: Retention is personal. We empower managers with a menu of options based on stay conversations. We ask what matters to each individual. Some people care about growth, others comp, others flexibility. You can’t just roll out one program and assume it works for everyone. So we’re creating customized retention strategies.

Jena: Love that! Last question. What are some growth areas or challenges you’re working on at Greenhouse?

Will: We’re maturing. Moving from startup to performance-driven. We’re implementing big systems, evolving into an AI-powered business, and facing increasing competition. Change management is tough, especially with a strong culture, but necessary. We’re learning how to stay innovative while adding the right structure. It’s a delicate balance.

Jena: So good. And yes, the ATS and HR tech space is crowded! You’re navigating it with intention. Are you hiring?

Will: We are! Check out our careers site. Connect with me on LinkedIn. I’m very active there. And like we said earlier, connections matter. If you’re curious, reach out. Greenhouse might be the right fit for you.

Jena: Amazing! Thank you so much, Will! This was such a great conversation!

Will: Thanks, Jena! Really enjoyed it.

Jena: See you next week for another episode of Culture Uncovered!