Yael (00:05)

Hi everyone. Welcome to another episode of Vertical Futures. My name is Yael Shemer. I'm the co-founder of Tulu. Today I have a very special guest — John O'Donnell, Director of Portfolio Operations at Woodmont Properties and a partner of ours. Today we're going to talk about resident experience, the future, the challenges that lie in real estate, and hear stories from John's own properties. John, thank you for coming to the show.

John (00:32)

Thank you so much for having me, and congratulations again on your Series A funding. The outreach was amazing and I know your product is really going to continue to be transformative.

Yael (00:44)

Thank you so much. It was really incredible to receive support from our partners and from residents using Tulu. I told my co-founder: the coolest thing beyond all is just getting actual notes from residents saying "I had no idea this is a startup, I had no idea there's so much purpose and intention that goes into this product." It was a really cool few weeks. Before we dive into your experience — you've been in the real estate industry for many years, you've been with Woodmont for many years. What got you started? What was it about those early days that made you want to choose this career path?

John (01:28)

When I was a senior in college, I had a strong advisor. Based on my skillset, he told me I should take an interview with a company called John Corker & Company up in the Boston area. I didn't know much about property management, but I thought it behooved me to take the interview and listen. I really loved everything they brought to the table — it was customer-facing, and I grew up in a hospitality setting around restaurants, so the foundation was there. They told me they'd give me a call when I graduated, and a couple of months later, the day after graduation, they called. I took the offer and figured I'd give it a try. I fell in love with it. I loved how dynamic it was — every day is a little different. You could be really focused on maintenance one day, doing a carousel of tours the next, focused on renewals the day after. I love how nimble this industry is, and I'm outgoing by nature. I love working with peers and customers and really trying to provide value and ultimately a win for everyone involved.

Yael (02:44)

That's awesome. Over the course of the last five years you've managed properties in over six states, moving from community manager to Director of Portfolio Operations at Woodmont. Tell us about the pivotal moments and insights that accelerated this trajectory for you.

John (03:26)

I work at Woodmont Properties and we're vertically integrated. I work with very talented people who are experts in what they do. I realized very early on that they were going to afford me a seat at the table, and I tried to just be a sponge and learn from everyone around me. Understanding that if I can understand construction better, finance better, where accounting is coming from — it will all impact me positively in property management. Separately, my mentor and manager — we've been partnered for the past five years — has been my biggest cheerleader as well as my toughest critic. She gives me honest, transparent, timely feedback consistently. That always provided me with the opportunity to understand exactly where I was in terms of personal and professional development, how to refine what I was working on, and what to double down on. At the on-site level, it's such a well-rounded business that you have to really take the time to learn all of it. You can't just focus on leasing. You have to understand maintenance, how the product was built, the mechanicals behind it. When you start seeing the need for a large-scale repair or a leak, understanding where the plumbing systems flow from is critical in those time-sensitive moments. I really took the time to do that, but not in a vacuum — I had an incredible support network around me with experts and talented associates I get to work with every day.

Yael (05:24)

Having someone who believes in you and a mentor who challenges you is priceless. You mentioned something that connects to my next question — the ground truth gap. In real estate, there's leadership and developers overseeing massive projects, and then there's the on-site team who actually see the crack in the wall, the front desk malfunction, all the granular things that influence the entire system. You work both hands-on at the property and at the portfolio level. What is the biggest disconnect you've observed between what happens on the ground versus what leadership thinks, and how do you bridge it?

John (06:27)

I was on-site for about 13 years and came up through the linear path — leasing professional, assistant manager, community manager, and growing my portfolio from there. Understanding what each level experiences day to day, the stresses involved, the high volume that can come in — it's not lost on me. A community manager can walk on-site first thing in the morning, before they've had their first cup of coffee or welcomed their team, and be hit with a leak, a sign that fell down at the community entrance — anything from A to Z. They're consistently putting out what I call micro fires. You have to bridge that gap because at a senior leadership level, there's always that macro strategy, those business objectives and outcomes you're driving toward. But the reality is you're managing people, and they're all experiencing different stress levels. The root of it all is proactive communication. Some managers are great at it — quick to raise their hand and say: here's what's going on, I'm not going to meet this deadline but I'm actively working on it. But other times you need to lean in and ask questions, because I truly consider myself support staff. We're in these positions to support the on-site teams and put them in the best position to succeed. I want to remove the stigma around asking for help. I want people to raise their hand and know that my response is going to be "how can I help?" — not "why can't you meet this deadline?" If we can remove that stigma and bridge that gap, everything moves in alignment and is more successful as a result.

Yael (08:56)

No problem is too small, and it's all part of a strategy that puts the resident first. Can you walk us through a few cases where you identified operational inefficiencies, mapped a process, and changed the framework around it?

John (09:42)

The bigger part of this conversation is really around the cross-functional relationships we have internally. We're vertically integrated, so we're working amongst peers — which is a game changer. This past year, we really made it a focus to create an artificial intelligence committee internally, comprised of essentially every department head and key players from each department. With that, we created a safe space to give open and honest feedback, evaluate the business, find potential gaps, and focus as a unit to support each other and identify what's priority. We create safe spaces with guardrails to test new AI, have feedback loops on whether something is benefiting the business long-term, or whether we gave it a try through a pilot and it's not a match — and we're happy we looked at it. We're a smaller operator compared to a Greystar, so being selective is important. The underlying value is really to work backwards: understand what the business case and the problem is, then work into the solution from there. That's something from the top down we're all aligned on. Property management was really the first benefactor of this committee. We put an AI software in place that functions 24/7 across phone, text, chat, and email. The intent is for it to work side by side with our on-site teams — to mitigate the high-volume, low-value conversations that eat up a chunk of their time, so we can repurpose that time on the low-volume, high-impact conversations. Like a renewal conversation. That's meaningful — you're talking about someone's residence, ensuring their happiness, really leaning in to identify anything that could improve or impact their decision to renew. We want to spend time in those conversations, not make residents feel rushed. And with alignment across departments, you get feedback from blind spots you weren't considering based on your own expertise alone.

Yael (12:50)

You've mentioned renewal calls and high-volume, low-value aspects of resident experience. How has the resident expectation changed over the last few years? And what are you noticing about the demographic of people living in Woodmont properties?

John (13:15)

We primarily operate in a Class A luxury apartment product, and in all of our markets we're seeing new starts increase exponentially year over year. In a competitive environment where your asset type is somewhat apples to apples — similar amenity package, product type, floor plan, size, and potentially rates — it really boils down to the customer service experience you can provide at the on-site level. Part of our onboarding process for new associates is shopping the competition to understand what's around you. You can walk away from a competitor tour and realize: I didn't really get to experience this at the level I expected. And then you compare that against what you're offering internally, and you very quickly understand the importance of providing that elevated service and making it a consistent focus. That's what sets you apart.

Yael (14:31)

That makes me think about how many times we get called to bring Tulu to a property after someone went shopping at a building that had it. Did you have a case where after a shopping experience you decided to change things in your own properties — or felt more confident in changes you'd already made?

John (15:10)

It gives our associates real confidence when they walk away from that process, because it's toward the end of onboarding and it makes you reflect on everything you've learned. You see it live in action and get a benchmark against your own expectations and internal standards. We rely heavily on feedback — not just analyzing data that comes in, but putting it into motion quickly and thoughtfully. We have resident online reviews, resident sentiment scores, and resident surveys across multiple touch points from prospect to move-out. We're always analyzing those for trends and patterns — are we missing the mark in any area? When trends are identified, we allocate resources to overcome those challenges, whether it's through our operations team supporting multiple communities or someone at the corporate level revamping a process that's become aged or less competitive.

Yael (16:51)

Is there an operational or experience trend you think the industry is sleeping on that will become more meaningful in the next three to five years?

John (17:01)

Self-guided touring. I think there was a significant amount of untapped potential there, which is quickly being realized across all asset classes — you can maximize touring opportunities beyond operational hours, which means potentially higher conversion rates. But I'm especially hopeful about where virtual reality goes as the market becomes more competitive and costs come down. I would love to see a world of digital self-guided tours where you don't have to leave your home — you put on a VR headset, and you take a carefully curated self-guided tour through a community with voiceover explanations of each room. That would be particularly meaningful for people who can't physically travel or are relocating from out of state. And with future advancements, you could probably measure a floor plan in a virtual reality environment — walk through your future apartment digitally before you even sign a lease and measure your balcony. That would be incredible.

Yael (18:31)

The future is already here. I've never heard someone describe self-guided tours like this. I think it's super promising. And as you know, we tailor Tulu to Gen Z and millennials, and one of the biggest things we're seeing is just the challenge of higher costs associated with moving to a new city. That's why we created Tulu — for people to move to a new location and not have to buy 15 to 20 appliances that are expensive and hard to store. When a property thinks about those things for you from day one — even before you move in — it automatically creates more trust and makes a real impact on how much you spend when you move somewhere new.

John (19:31)

100%.

Yael (19:31)

Let's talk a little more about you. I joined you and your team on a few calls and I could really sense the appreciation your team has for you as a leader. How has your leadership philosophy evolved, and is there one thing you wish you knew earlier in your career that has now become a guiding principle?

John (19:56)

Earlier in my career, particularly as a community manager, I really tried to shoulder the burden of everything. Ultimately it all falls to you on-site regardless of the scenario. I tried to make it all happen in a vacuum and didn't give my team the ability to step up, to take on things that would stretch them and accelerate their growth. That did not come easy to me — I was somewhat stubborn in my earlier years. But once I leaned in and made delegation a focus, and saw the value it could provide and the unlocked opportunities it could provide my team — I think one of the most rewarding things you can have as a manager at any level is to see your team win. Particularly a high-visibility win that impacts the company at scale, or a win in the eyes of a resident that results in a significantly positive online review. At this level, I really focus on building confidence in my team. They're in these seats for a reason. I want to give them a safe space to make decisions, but know that I'm going to support them regardless of the outcome. If we win, it's their win. If we fail, we fail together and we learn from it. Making organic mistakes is how you learn fast — the trick is trying not to repeat them. I'll always be a people manager first, even at the expense of my own work. If you raise your hand and need me, I'm there, regardless of time or day. I make it a priority to get to know my team on a personal level. That rapport turns into trust. And when I show up for them, they'll show up for me. We're all human at the end of the day, and if we spend time to get to know each other, understand how each other ticks, things fall into place. It almost feels seamless — it makes it fun.

Yael (22:28)

I very much relate to that. There's really no other way to work well with other humans than by showing up as who you are, having immense respect for people's goals, and making progress together. As we get toward the end of the interview — what is one thing you think is going to become a really big challenge for the industry, and one opportunity you and your team are looking forward to?

John (23:15)

The biggest challenge is how we optimize workflows and processes with artificial intelligence while still maintaining that high level of personalized customer experience — maintaining those face-to-face conversations. If they're not happening organically, you have to find opportunities to consistently make them happen: resident events held more frequently, a monthly town hall where anyone can pop in and reach the office team virtually or in person. You want to be approachable. You never want to lose sight of the fact that you're there to support residents and make their lives easier. On the opportunity side — understanding the feedback we get. Our people division is amazing at generating associate feedback through internal surveys, and it's no surprise we've won awards at both the state and national level as a result. They seek feedback so often, aggregate it, share it with senior leadership, and we can actually put change into place. Everyone buys into that culture, and it snowballs in the best way — we're all working toward the same goals, and we all want each other to have a great place to work. If your associates love what they do and love showing up every day, the business results will take care of themselves.

Yael (25:40)

100% — amazing and inspiring. Last question: if you could redesign the future of multifamily and resident experience without any constraints, without any legacy, what would it look like?

John (26:02)

I envision a world of multiple scenarios, and I would love to see a path where you can still have your traditional experience — walk in for a tour, sit down with someone, work through every step of moving. But I'd also love the ability to pick and choose what we can automate. In a world of tech, you can have online checklists that automate reminders for people with busy schedules who can't always be physically present. Set up your utilities — it automates an email, due by this date, here's the link. The move-in process itself could be completely touchless. If you can't get there during business hours, that's friction, and we have tools to overcome that. That's a win in the eyes of someone with a heavy corporate commute. But the real vision is this: we can make the experience as personal or as tech-heavy as you'd like it to be. We want to customize the experience around what you're actually seeking — not just what we're willing to offer.

Yael (27:30)

A personalized experience — that is the future for sure. I think many residents will appreciate it and would want to stay in your properties for as long as they can. John, thank you so much for joining me today. I very much enjoyed the conversation, and I'm sure our listeners will find immense value in the lessons you've shared.

John (27:55)

Thank you so much for having me. I really enjoyed it.