🌅 From Tragedy to 93 Doors: How One Operator Built Ocean City’s #1 STR Brand With Steve Resnick
“It’s not happening to you. It’s happening for you.” — Steve Resnick
There’s a moment in this episode where Steve casually mentions a poster board hanging on his bedroom door — 120 little squares, each one waiting for a sticker that represents a new property under management. Every morning, he sees the squares. Every morning, he asks himself the same question: what do I need to do today to get closer to the goal?
That single image tells you almost everything you need to know about how Steve Resnick operates. In a short-term rental industry full of operators chasing growth in every direction, Steve’s discipline is almost old-school. Pick a number. Make it visible. Make decisions through it.
This conversation digs into how that focus translated into 93 properties in Ocean City, New Jersey — and what it actually takes to deliver consistent five-star experiences at that scale. 🏖️
👤 Meet Steve Resnick
Steve Resnick is the visionary founder and CEO of HeavenlyRez Vacation Rentals, the fastest-growing short-term rental company in Ocean City, New Jersey. He has redefined what modern hospitality looks like — blending technology, heart, and human connection to deliver a five-star experience for both guests and homeowners.
Under his leadership, HeavenlyRez was ranked #1 Property Management Company by AirDNA in 2025 for the Ocean City, NJ market and has earned thousands of five-star reviews — the most in the region. The company maintains an industry-leading 6.5-minute average response time and offers 24/7 guest and owner support.
Steve is a Certified Short-Term Rental Co-Host, Multi-Year Golden Host Award Winner, and STR Secrets Boardroom Member. He’s been featured on multiple short-term rental podcasts, served as a panel speaker at the STR Wealth Conference, and is a #1 Best Selling Author for his contribution to Hospitable Hosts: Couples Edition.
🧭 The Origin Story Behind HeavenlyRez
Steve’s path into hospitality wasn’t planned. After more than 20 years in technology program management at a major financial institution, he and his wife Kim bought a beach property in Ocean City in 2015 — somewhere to make memories with their young daughter.
Then came tragedy. Their four-year-old daughter passed away. The property they’d planned to fill with family vacations became something else entirely: a place to rebuild.
When they eventually had another daughter, they returned to Ocean City and started thinking about creating that experience for other families. Frustrated with the local management company handling their rental, Steve took it over himself — and the numbers immediately spoke for themselves. One property became three. Then COVID hit. Then a neck injury sidelined him from his corporate role. He used the recovery time to get his realtor’s license, build a vision, and commit fully to the business that had been quietly growing on the side.
Three years later, he’s at 93 doors with a clear runway to 120 by the end of 2026. The chapter he co-authored in Hospitable Hosts: Couples Edition is appropriately titled Never Let a Good Crisis Go to Waste. 🌊
🎯 The Vision Board That Drives Every Decision
The poster board on Steve’s bedroom door isn’t just motivational decor. It’s a decision-making framework.
When he started hiring, he didn’t hire for where the business was — he hired for where it was going. When he evaluated whether to lease a 5,800-square-foot commercial building (the new HeavenlyRez Hospitality Hub), the question wasn’t do I need this today? It was will I need this at 120 doors and beyond?
This is the kind of forward-looking discipline that’s easy to nod along with and surprisingly hard to execute. Most operators react. Steve plans the gap between current state and target state, then closes it methodically.
For more on this mindset shift, the scaling a short-term rental business with systems breakdown covers why infrastructure has to outrun door count.
🏢 Why HeavenlyRez Built a Centralized Hospitality Hub
One of the most fascinating operational decisions Steve shares is the move toward centralizing inventory and amenities in a dedicated facility — instead of relying on owner closets at each individual property.
His logic is brutally honest: every property is essentially a separate warehouse. Owners leave closets unlocked. Cleaners can’t always control what guests take. Inventory levels vary by location. At three properties, you can manage that chaos. At 93, you can’t.
By consolidating amenities — standardized Keurig and drip coffee makers, beach chairs, beach tags, luxury essential kits with shampoo and conditioner, paper goods, even pizza cutters — into one central hub, HeavenlyRez removes variability from the guest experience. A guest who books a beachfront condo gets the exact same amenity standard as one who books a bayfront unit.
“The most important thing for a guest is their first impression. Is it clean? Is it consistent? When you go to a Marriott, you always know what you’re getting. I wanted that for every single one of our properties.”
This kind of standardization is also why HeavenlyRez doesn’t take properties outside Ocean City. Geographic focus isn’t a limitation — it’s the unlock. The team, the warehouse, the SOPs, and the cleaning crews are all built around one market.
🛠️ Inside the HeavenlyRez Tech Stack
Steve’s background in technology shows up in nearly every layer of the operation. The current stack includes:
- OwnerRez as the PMS (with Hostbuddy and Resi AI layered in)
- Breezeway for cleaning, inspection, and maintenance workflows
- Go High Level as the CRM, contracts, marketing journeys, and concierge store engine
- StayFi for guest WiFi capture and post-stay nurture
- PriceLabs for dynamic, supply-demand-driven pricing
- Point Central for smart locks, smart thermostats, water sensors, and patio-door sensors
- Monday + Microsoft Teams for project management and SOP storage
The smart device layer alone is doing meaningful work. Unique guest codes are auto-generated and activated only during the check-in window. Thermostats automatically shift to eco mode the moment a guest checks out. Door sensors shut off the AC if the patio door is left open for more than 10 minutes. Water sensors have prevented countless leaks before they became real damage.
This is the kind of infrastructure that enables HeavenlyRez to deliver a 6.5-minute average response time — because the system flags problems before guests or owners ever have to.
🤖 Where AI Fits Into the Operation
The most forward-leaning part of the conversation is about AI. Steve is doing a few things that most STR operators haven’t even considered yet:
A virtual inspection system built in Claude. Cleaners upload photos through Breezeway, and Steve’s custom AI workspace reviews them — flagging things like streaks on a kitchen counter that a human inspector might miss. When damage is reported, the AI even pulls replacement costs from Amazon and pre-fills the claim for Safely, his damage protection provider.
A CEO executive dashboard that visualizes every KPI he tracks — built using direct API calls to OwnerRez.
Daily email scanning that surfaces action items, regularly scheduled tasks, new listings hitting his market, and industry news he should be aware of.
Welcome book automation, concierge store redesign work via Claude Code, and ongoing experiments with connectors to PriceLabs, Canva, Gamma, and more.
If you’re starting to think about how AI fits into your own operation, the AI guest communication conversation with Sabrina Mulligan is a great companion listen — and the property descriptions strategy for AI search is worth bookmarking for anyone thinking about discoverability in the next era of guest behavior.
🧱 The Hiring Philosophy Behind a Five-Star Team
Steve’s team includes seven cleaning crews, a hospitality manager, a director of operations, a full-time marketing manager, and a 24/7 guest support team — something he points out no other operator in his market offers.
His hiring approach is simple and uncompromising: hire slow, fire fast, and only bring in A players who genuinely care.
He shared a principle that translates across any growing organization:
“You can teach the business. You can teach the tech stack. But you can’t teach someone to care.”
Core values aren’t poster decorations at HeavenlyRez. They’re the decision-making framework when Steve isn’t in the room. Treat everyone the way you’d want to be treated. Correct the process, not the person. When something goes wrong — and it will — the team looks for the underlying process gap, not the person to blame.
For more on building teams that scale without the founder bottleneck, the scaling an STR portfolio with intention conversation with Fouad Bazzi and Jacinda Neustel covers similar territory from a different angle.
📨 The Direct Booking Engine Behind HeavenlyRez
Steve doesn’t separate operations from direct bookings. They’re the same thing.
The repeat-booking strategy is built on three pillars: deliver a five-star stay every time, capture the guest at every touchpoint, and stay top of mind year-round.
Pre-arrival emails set expectations. StayFi captures guest emails and routes them into a Go High Level journey. Mid-stay check-ins make sure the experience stays on track. Post-stay nurture keeps HeavenlyRez in inbox view long after the trip ends — local tips, hidden spots most tourists miss, monthly newsletters, and announcements when new properties come online.
The point isn’t to be loud. It’s to be remembered. When a guest plans next year’s beach trip, the goal is for them to skip Airbnb entirely and book direct because the relationship already exists.
If you’re building your own version of this funnel, the destination marketing direct bookings episode with Jennifer Barbee and the STR brand identity conversation with Lisa Roads are both worth your time.
📚 Steve’s Book Recommendations
- Think and Grow Rich by Napoleon Hill — Steve’s all-time favorite and his go-to recommendation
- Unreasonable Hospitality by Will Guidara — a book about a restaurant operator that Steve says applies to anyone in hospitality, and one that mirrors the standard he’s chasing at HeavenlyRez
⚡ Rapid-Fire Highlights
📖 A book that has inspired you? Think and Grow Rich (all-time go-to) and most recently Unreasonable Hospitality — about a restaurant owner, but the mindset applies to any hospitality business.
🧠 Mindset advice for someone starting something new? “Believe the universe is always working for you. Things will go wrong — it’s a matter of when, not if. Look for the learning opportunity in every issue. It’s not happening to you. It’s happening for you.”
🎯 One tactical thing someone could implement this afternoon to grow direct bookings? “Have a process. Understand what it’s going to be and focus on it. At the core of everything, it’s about how you treat others. Come with a heart of service. Take small steps. Get better at everything you do. People relate to that — and the repeat bookings follow.”
🤝 Connect With Steve
You can follow Steve and HeavenlyRez through his Linktree: https://linktr.ee/heavenlyrez
For everything HeavenlyRez (website, social, listings, reviews): HeavenlyRez.com
He’s also active in the STR Secrets Mastermind community and is happy to connect with fellow operators looking to compare notes on operations, tech, and scale.
🚀 Ready to Build Your Own Direct Booking Engine?
If Steve’s story made one thing clear, it’s this: the operators who own their guest relationship are the ones building businesses that last.
🎧 Listen to the full episode of Booked Solid for the complete conversation — including the full breakdown of the hospitality hub, the AI inspection system, and the operational philosophy behind 93 doors of consistent five-star stays.
🌐 And when you’re ready to take ownership of your direct booking experience, head over to CraftedStays.co to launch a fast, mobile-optimized, conversion-focused direct booking website built specifically for short-term rental operators. No WordPress. No agency invoices. Just a platform purpose-built to help you turn traffic into bookings.
💬 Join the community of hosts building independent booking brands. Subscribe to the Booked Solid newsletter, connect with us across our podcast guests, and get the strategies that the top operators in the industry are using right now.
Steve: Believing that I could do it for one — and keeping it top of focus in my mind. So I literally have a poster board of 120 little squares. Every time I get up in the morning, I look at it and see where I’m at and remind myself: what do I need to do today to get to my goal?
Every time I get a property, I have these little stickers. I create a little label, put the property address underneath, and stick it on the poster board. Once I get to 120 of these, I’ll be where I need to be. That’s just a constant reminder — one of many things I do to make sure I don’t lose sight of my vision and my goal.
Gil: Before we bring on my guest, I wanted to talk briefly about something I’ve been hearing a lot from hosts. I keep hearing the same thing: “I know my website isn’t converting, but I can’t afford $8,000 on an agency to rebuild it.”
Here’s the thing — you’re driving traffic with all these marketing strategies, but if your site isn’t built to convert, you’re basically lighting your energy and money on fire. And even if you could afford an agency build, every time you want to test something or make a change, you’re paying them again. You can’t iterate. You can’t test. You can’t really improve.
You don’t need a custom $10,000 website to get the conversion rates that really matter. You just need the right platform. That’s why I built CraftedStays. It’s purpose-built for short-term rentals and designed from the ground up to help you drive more direct bookings. You can finally turn that traffic into bookings, and you can keep testing and improving — all on the platform. You don’t need to learn something new.
If you need help or want to get started, head over to CraftedStays.co and start your free trial. Now let’s bring on our guest and dive deep into hospitality and marketing.
Hey folks — welcome back to the Booked Solid Show, the show where we bring in top operators to discuss operations, hospitality, and direct bookings.
On today’s show, we have Steve Resnick. He’s the owner of HeavenlyRez, manages over 90 properties, and on today’s show we go deep into how he scales operations. We discuss his tech stack, how he keeps a consistent guest experience, and the things he invests in to drive repeat bookings. Without further ado, let’s bring him on.
Gil: Hey Steve, welcome to the show.
Steve: Hey Gil — thanks for having me. Excited to be here.
Gil: You’re the first Hospitable Hosts: Couples Edition co-author I’ve had on the show. Well, I recorded with Rosa Long a while ago, but that was before we had to collaborate on the book. Great to have you here.
Steve: Great to be here as well.
Gil: For our listeners — Steve and I and many others co-collaborated on a book called Hospitable Hosts: Couples Edition. I dunno if “project” is the right word — that probably undermines the effort that went into it. But it was a journey. I was involved for at least a year, from when I first talked to Jody until the book was eventually released, and then all the marketing that comes after.
For me, the most fulfilling part of co-authoring that book was the introspection. You go through this growth — all the pain and suffering and everything that comes with starting something on your own — but you don’t usually get a chance to reflect back on it and think about the little micro-stories that happened along the way. The book kind of forces you to do that. That’s one of my big encouragements for anyone considering writing a book about themselves. It’s a great way to learn about yourself and reflect.
Steve: Yeah, for sure. When I first met Jody, we were talking about another book I was getting involved with — it was more property-focused. We started going down that path, and then I found out about the couples edition. The inspirational ideas and stories, working directly with my wife on the business, the journey we’ve been through to build this business, the things we’ve done, the tragedies, the blood, sweat, and tears — it just seemed like a great fit. I told Jody, “I need to be a part of this other book. Can I switch? Is it too late?” She agreed, thankfully.
My wife and I were fortunate to be a part of it. The chapter we wrote was titled Never Let a Good Crisis Go to Waste — which is really meaningful given some of the hardships we dealt with and the origin story of HeavenlyRez. I’m just happy we had the opportunity. Great experience.
Gil: Maybe to give us an introduction — that’s a good lead-in for folks who want a small synopsis of the story inside the book. Do you mind introducing yourself?
Steve: Absolutely. My name is Steve Resnick. I’m the owner and co-founder of HeavenlyRez Vacation Rentals. We have 93 listings under management, all in Ocean City, New Jersey. It’s been a great experience. In addition to co-authoring that chapter, I’ve been on several podcasts. I’m actively involved in the STR Secrets Mastermind and part of the Secrets Boardroom. It’s been great sharing operational successes, helping teach others — and learning from others as well. It’s a two-way street.
Gil: I definitely want to dive into the things you’re passionate about, especially on the operational side. Right before the show we were talking about AI, so I want to dive into that too. Maybe tease us first — you have 93 doors now. What was that growth like, and can you give us a peek into some of the tragedies that led you there?
Steve: I started in the corporate world. I worked for a large financial institution for over 20 years. My last role was in technology program management, so a very heavy tech background. I also have an MBA in marketing. In addition to managing very large technology projects and programs, I ran process improvement initiatives for financial firms.
What I learned from all that is there’s a lot of complementary skills between process, marketing, technology, and people management — and the short-term rental business. My journey started in 2015 when my wife and I bought a property in Ocean City. We’re from the Philadelphia area, so Ocean City was the place we’d go for vacations. We went there with my family, with my daughter.
Long story short, we had a tragedy. My daughter, when she was four, passed away. It was a rough time. Every year we would go to Ocean City and create memories there. After she passed, it was hard, but we eventually got back on our feet and decided to move forward. We bought a property in Ocean City because we had so many memories there with her, and we wanted to create new memories.
We eventually had another daughter, brought her there, and spent lots of family time — beach, ocean, boardwalk. We decided we wanted to create that kind of experience for other people. I wasn’t happy with the way the management was going on the property I had bought as an investment. I had no idea what I was getting into, but I learned a lot. The kind of person I am — I was passionate about making things better from a process perspective. I wanted to be less transactional and more focused on hospitality.
I bought a property and it did really well. When I took ownership of management, I was making a ton more money than when it was managed by one of the local realty companies. So I bought another one — same result. Then a third. Then COVID hit, and I panicked a little. I had cancellations. They eventually rebooked, but at that moment I realized I had all my eggs in one basket. At the same time, my company was relocating me out of state.
So I sold one property to a gentleman who was like, “There’s no way you’re making this kind of money on this property. It’s way above market.” I showed him the numbers. I think he thought I was fudging them. He bought it anyway and asked, “If you really make that kind of money, would you mind managing it for me, since you’ve already managed it for yourself?” I said, sure. We did exactly what we said we would do. He came back and asked us to manage another beachfront property. Then the next year, he said, “I want to buy one more property — but I’m not buying it unless you and Kim manage it for me.”
I looked at Kim and said, “I think we have a business here.” It started as a side hustle while I was working full-time. Then I had another tragedy — I woke up one morning with my right arm completely numb, like a permanent funny-bone feeling. I went to several doctors and eventually needed neck surgery. I knew I’d be out of commission for a while. I used that downtime to elevate my game in the area I was actually passionate about — hospitality, entrepreneurship, putting all the pieces together. I got my realtor’s license. I created a vision and a plan: 120 properties by the end of 2026. That was three years ago. I’m at 93 now. I’m on target. I’ll get there.
Things are happening according to my vision, and I couldn’t be happier with the team I’ve built. Eventually I got to a point where I was doing way too much on my own. That’s when I joined the STR Secrets Mastermind. I realized — there has to be a better way. I learned the operational pieces required to build a team. I had bought myself a job, and I needed to get out of that. To scale to the next level, I needed great people. That’s when I started building the team out. Couldn’t be happier where I’m at now.
Gil: That’s amazing. You set a target of 120 properties by end of 2026. You’re at 93 now, on pace to hit it. What do you think led you to being able to consistently hit those milestone markers?
Steve: Believing I could do it. And keeping it top of focus. I have a poster board with 120 squares on the back of my bedroom door. Every morning I look at it and ask: what do I need to do today to get closer? Every time I get a property, I create a little label with the address and stick it on the board. Once I get to 120 stickers, I’ll be where I need to be. It’s a constant reminder — one of many things I do to stay focused on the vision.
Gil: You’re almost training your brain to keep that goal in focus. As you make decisions throughout the day, you’re constantly reminded of where you’re going.
Steve: Yeah — it makes decisions easier. My decisions are always based on the goal. I didn’t hire based on where I was. I hired based on where I’m going to be. At 120 properties, will this team be enough? Where do I need to be, and how do I phase that in?
Most recently, we purchased a commercial building. We call it the HeavenlyRez Hospitality Hub — 5,800 square feet. I bought it because I need that level of operational excellence to support 120-plus properties. 120 is the starting point. We’re going way higher. To operate at a high level of quality and deliver consistent five-star experiences, I figured out we can’t do that out of owner closets at each individual home. It just doesn’t work at scale.
We’re fortunate — we’re at the top of our market. We have the most five-star reviews of any company in Ocean City, which is significant because most of our competitors have been around for over a hundred years. We were ranked #1 in property management by AirDNA in 2025 for our market. But I’m not resting. I had to reimagine my entire operational process for this coming season, and the operations hub is part of that vision.
Gil: When did you purchase the hub? And what triggered it — was the seed already growing on you?
Steve: I always look at what we can do better. I analyze every guest review, every owner comment — looking for the nugget I can take to improve. Last year, we had a consistent theme: there was a lot of pressure on cleaners, and a guest’s first impression matters more than anything. If you walk into a property, the first thing should be: does it smell clean? Does it look clean? Do you get a consistent experience?
I wanted that consistency to be standard and repeatable for every guest. That’s why every single property we manage has a standardized set of amenities. Every owner buys a Keurig and a drip coffee maker. Beach chairs. Beach tags. Pizza cutters. Everything is standardized.
We’re now rolling out luxury essential kits — shampoo, conditioner, body wash, lotion, makeup remover, soap. Toilet paper, tissues, paper towels, coffee. Standardized across all 93 properties. Guests know exactly what they’re getting. They know what to bring or not bring.
The problem with a fragmented model is variability. You have many people, many warehouses. I think of every property as a separate warehouse. It’s much better to operate from one centralized hub than from 93. With 93 owner closets, you don’t know if an owner left it open and the next guest helped themselves. You don’t know if the cleaner left it open. You can’t put a camera inside a closet. You’ll never know what really happened.
The only way to truly centralize control is to centralize it in your own facility. It might work to operate from owner closets when you have a few properties, but at a certain point you start losing. You see large operators — as they scale, the first thing that fails is their cleaning operation. Quality starts to fall apart. I never want to get there. That’s why I’m building the foundation now to support scale at high quality.
Gil: There’s a huge advantage of economies of scale here. Rather than fragmenting and saying, “I want to grow to 120 doors anywhere,” you’re centralizing in one market. That lets you build a team, control SOPs, manage performance directly. And the centralized hospitality hub solves the variability problem from the inventory side too.
Steve: Exactly. The fact that we’re only in Ocean City is intentional. We can stay at this scale and keep our quality on point. I get requests all the time to manage properties in nearby markets, but right now I’m hyper-focused on getting our operations dialed in — making sure our team is trained the same way on the same SOPs, checklists, and quality standards.
Gil: As you scale, are there core principles you consistently come back to — things you won’t compromise on?
Steve: The most impactful thing is our core values. Those are our team’s decision-making framework. They know how we operate, what we’re about, our culture. If Steve isn’t there, it doesn’t matter — these are the company’s philosophies. Treat everyone the way you’d want to be treated. Correct the process, not the person.
When something goes wrong — and it will, we’re never going to be perfect, but we always strive for perfection — we don’t point fingers. We look at what underlying process needs improvement so it doesn’t happen again. Continuous improvement is part of our culture. It’s about learning and growing, not staying stale — which is what most of our competitors are doing in our market.
We’re on the bleeding edge of technology. Our tech stack is top-tier in the industry. We’re constantly learning what’s happening on the AI front and how it’s going to change the future. You always want personal interaction in hospitality, but there are so many operational backend things our team can be doing with AI that essentially give them superpowers — 10x the productivity of every person on the team.
Gil: We have very similar principles at CraftedStays. We’re hiring customer success managers, and we realized aptitude is less important than attitude. We want them strong in the things we care about — proactive responsiveness, thoroughness, customers being able to trust us. We can teach the business, the tech stack, all of it. We can’t teach someone to care. That’s ingrained. I get the same sense from your hiring approach.
Steve: Yeah, absolutely. We try to hire slow and fire fast. We want only A players. If you’re not an A player, the rest of the team won’t want to be around you anyway — they’ll call you out. We want top performers who care about other people, who are genuine, and who support our core values. If there’s no alignment between an individual and the company’s culture, it’s not a fit. You usually know that upfront.
I’m fortunate to have a phenomenal team. We went through trials and tribulations. We fired a lot of cleaners last season. Now we have an awesome set of cleaners — seven different cleaning crews. We have a hospitality manager instilling checklist items, photos, rigor. A great director of operations. A full-time marketing manager helping with social media across Instagram, Facebook, YouTube, and now TikTok — which I was originally against, but got pulled into. Our 24/7 guest support team is amazing. Surprisingly, no one else in our market offers 24/7 support.
Gil: You mentioned investing heavily in tech and staying on top of AI. Let’s talk about both. What does your tech stack look like and how has it evolved?
Steve: We’re heavy on tech. OwnerRez is our PMS — we live and breathe in there, and we use Resi AI a little, plus Hostbuddy. Breezeway is our maintenance, cleaning, and inspection system. We rolled it out to all our cleaners — one system of record, integrates nicely with our financial tools.
We use Go High Level as our CRM to stay in contact with guests and owners. It’s not just a CRM — we use it for contracts, marketing journeys, business development tracking, and we’re rebuilding our concierge store on it. The store offers things like golf cart rentals (a big hit last summer), bellhop services, beach caddy services, private chefs, grocery pantry stocking.
We use StayFi for a frictionless guest experience. When guests log into the WiFi, they get redirected to a landing page with a custom welcome book, the option to rebook for next year, access to the concierge store, and more.
Point Central handles our smart devices. Guest codes are created automatically — every guest gets a unique code that activates only during their check-in window and gets deleted after. Smart thermostats know when a guest checks out and shift to eco mode automatically, then cool down before the next guest arrives. Door sensors detect if a patio door has been open more than 10 minutes and reduce the AC to avoid taxing the system. Water sensors have prevented countless leaks. All of it is automated.
Gil: I love it. Years ago, before e-commerce, I was in IoT. I worked at August on the Yale and Schlage integrations, then at Samsung. So I know how complex it is to roll this stuff out at scale. Without the right systems, doing it across 90+ doors is really hard.
Steve: It’s important for owner success too. We want to care for properties like they’re our own. If a temperature alert hits — say it spikes to 80 degrees — my local operations manager gets the alert: “Something’s wrong. AC’s not working.” We know before the guest knows. Same thing for internet outages, lost power, HVAC issues. Real-time alerting to my local team.
Gil: Did you build the system yourself? Did your ops person build it? Who’s the driver?
Steve: The tech side comes from me — that’s my background. But I’ve created SOPs for everything I do. When I do something more than once, I document it. We do a Loom video of every process. That’s how I trained my property care operations manager on all the tech and installations. He implements everything now. I don’t deal with it. Hundreds of detailed SOPs across the business.
Gil: How about knowledge management — where do all those SOPs live?
Steve: We use Monday for project management and Microsoft Teams for file storage. Then AI sits on top of that — we can query all our SOPs through it. We started with Company Knowledge in ChatGPT using OpenAI, but I’ve been spending a lot of time on Claude and Claude Cowork. We’re migrating into using that across various areas of the business.
We also use custom fields in OwnerRez. Our AI can read into the custom fields to pull information. The thought process is: document everything. We know where the water shutoff is, the gas shutoff, the electrical panel, the make and model of every appliance. That’s all part of a knowledge base the team can access in real time.
Gil: Right before the show you were sharing some AI dashboards and automations you’ve built. Do you mind walking through the use cases that have made the biggest impact?
Steve: The impact is just getting started — these tools are still maturing. But I’ve implemented some really cool things. I have a CEO executive dashboard that visualizes all my KPIs — real-time insight into the data I need to make decisions. I have AI scanning my emails daily for action items, regularly scheduled tasks, new market listings, and STR industry news so I stay current.
On the operational side, we automate welcome book creation. I’m using Claude Code to redesign and reimagine our concierge store. We strive to physically inspect every property after every cleaning, but if we can’t, I built a virtual inspection in a Claude space. It reads the cleaning report photos from Breezeway and the checklist items, then identifies things like: “Hey, you may want to go back to this cleaner — there’s a streak on the kitchen counter.” I didn’t even notice it. I’d look at the photo again and Claude was right.
It even handles damage claims. If the cleaner reports damage, the AI goes onto Amazon, finds replacement costs, and feeds the claim information to Safely, our damage protection provider. Tremendous time savings, at a level of detail a human can’t match — at higher volume too.
Gil: We’re in an amazing time. Previously, building any of this would require hiring a team and waiting months. Now you can have an idea, work through it independently, stitch things together, and get clarity faster than ever.
You mentioned using OwnerRez APIs for the dashboard. Are you experimenting with MCPs — connectors that let Claude pull from your other tools?
Steve: Yeah. In Claude I have PriceLabs connected — that’s our dynamic pricing tool. I didn’t mention it in the stack, but we’re strong believers in supply-demand, data-driven pricing. PriceLabs helps optimize income for our owners and keeps us competitive. I also have Canva connected for marketing collateral, Gamma for presentations.
I don’t have the OwnerRez MCP yet, but I’m looking forward to using the one you created. I’ve been using direct API calls, which has been working for CEO-level reporting — but there are definitely more opportunities to investigate. Some OwnerRez data isn’t available through the API for some reason.
Gil: Yeah, OwnerRez has some data that isn’t open by default. The messaging endpoint, for example, needs to be unlocked through OwnerRez before you can access it via API. I built the MCP because I’m an OwnerRez user myself. In the beginning it was just about getting access to the reports I usually go to — OwnerRez has a great reports dashboard, but I live and breathe inside Claude.
Then I started transitioning to year-over-year analysis, comparing months over months. It’s nice to manipulate the raw data using natural language instead of dropdowns. The unique unlocks are when you stitch information together. You can see guest density across properties. You can see whether you have more families in summer versus winter using guest counts. A fun one is asking Claude to look through all your reviews from the last six months to flag anomalies — anything mentioned repeatedly that you should fix on the operational side. It can build full dashboards. You can even cross-reference cleaning teams against review patterns.
Steve: That’s a great idea — I didn’t think of that one. Love it. We’re definitely going to do that.
Gil: That’s the biggest difference between an API and an MCP. With an API, you have a defined input and output for one specific data set. With an MCP, you give the AI access to certain tools, and Claude can use natural language to combine four different APIs to answer your question. The MCP is essentially a bridge for LLMs because they can’t really understand raw APIs the same way.
Steve: Have you had conversations with OwnerRez about opening up some of those endpoints?
Gil: Yes — I know Chris, the CTO at OwnerRez, quite well. There are a few things I want to open up. One is the ability to write back into property descriptions. Right now you can pull descriptions out, but you can’t write back in. Since we’re heavy on direct bookings, we want to optimize listing descriptions based on seasonality. For the holidays, we want to mention that we decorate properties, that we welcome family holiday stays — those things make guests feel like the experience is intentional for them.
But it’s a lot of work across 90+ doors. If you can instruct Claude to take existing descriptions, store them somewhere safe, and modify based on seasonality — and have the AI show you a sample of changes before writing anything — that gives you traceability. You don’t want to go YOLO mode on something that important. That’s how I think about designing systems and fallbacks.
Steve: Yeah, that makes sense.
Gil: You mentioned StayFi on the marketing side. What does your direct booking tech stack look like? Are you focused more on attracting repeat bookers, or driving new eyeballs?
Steve: A bit of everything. It’s important for us to stay in contact with guests throughout the year — not just during their booking. We send pre-arrival communications so they know what to expect of the area, events going on, things to know before arriving, plus our custom welcome book.
During their stay, we check in to make sure things are going well. After their stay, we want to maintain the relationship. StayFi integrates with Go High Level and puts guests onto a journey. We capture their info to send value across the year — “Hey, did you know there’s a really cool local spot most tourists don’t know about?” Little nuggets, tips, tricks. We want to build a relationship so we’re top of mind. Next time they want to come back, they book directly with us.
We have a newsletter too. Anytime we launch a new property, we blast our list. We send a monthly newsletter to guests and owners to keep everyone in the loop.
Gil: Anyone who stays with you experiences a high level of hospitality. The engine for direct bookings is making sure they always have a five-star stay — and then having the systems to capture the email, build trust over time, so the next time they’re thinking about Ocean City, they’re not opening Airbnb. They’re coming directly to you because their experience exceeded what they expected.
Steve: Exactly. And it ties back to the standardization across our portfolio. We hope they come back to the same property next year, but families change — they grow, they shrink. They sometimes want a bayfront instead of a beachfront. We have a wide variety, so we make sure they understand: even if this property doesn’t fit this year, we have other options, and you’ll get the same level of hospitality and consistency. Plus significant cost savings when they book direct vs. Airbnb or Vrbo.
Gil: Awesome. Steve, this has been a pleasure. A lot has changed even since the book was published — especially around the tools available to all of us. It was fun geeking out with you on this.
Steve: Yeah, well, thank you, Gil. I appreciate it.
Gil: We usually end the show with three questions. First — what’s a book you’ve read or collaborated in that has really inspired you?
Steve: My all-time favorite is Think and Grow Rich. That’s always my go-to recommendation. Most recently, the book that hit home for me is Unreasonable Hospitality. It’s not STR-focused — it’s about a restaurant owner — but so much of it applies to any hospitality business and to mindset overall. Mindset is where it’s at. It’s top-of-mind on the core values everyone in hospitality should be striving for.
Gil: Second question. What’s one piece of mindset advice you’d give someone starting something completely new?
Steve: Believe the universe is always working for you. Everything happens for a reason. Things will go wrong — it’s a matter of when, not if. Have the mindset of “what’s the learning opportunity here, and how can I grow?” In every issue or circumstance, something is being done for you, not to you. That’s a big differentiator. If you have that mentality, you’ll be successful.
Gil: Last question. We talked a lot about marketing tactics, operations, all of it. What’s one piece of tactical feedback — something someone could implement this afternoon to either start direct bookings or amplify them?
Steve: Have a process. Understand what it’s going to be and focus on it. It doesn’t have to happen overnight — just start moving in that direction. At the core of everything you do, it’s about how you treat others and the service you provide. If you do that consistently, you’ll get repeat bookings, and those repeat guests will want to come back specifically to you. Have a heart of service. If you don’t, it’ll show quickly. Regardless of the tools or technology, none of that matters without that core. Take small steps. Come from a heart of helping. Get better at everything. People relate to that.
Gil: 100% agree. The folks with the strongest direct booking rates are usually the ones with the strongest reviews and the strongest customer satisfaction — the ones who leave guests thinking, “I really want to go back, and I want to tell people about this.” Those are the operators who win on direct.
Steve: Yeah, for sure.
Gil: Awesome, Steve. It’s been a huge pleasure. If folks want to follow you or get in touch, where can they find you?
Steve: @HeavenlyRez on all social channels, and HeavenlyRez.com. Reach out anytime — we’re always happy to help.
Gil: Awesome. Thanks, Steve. Can’t wait to catch up after this. Appreciate having you on the show.
Steve: Thanks for having me. I appreciate it.
Gil: All right.