How Curated Vacation Properties Saved $250K with Topkey

Curated Vacation Properties is not a startup finding its footing. It is a three-time Inc. 5000 honoree, one of America's fastest-growing private companies, managing 125 listings across Charleston, South Carolina, generating over $10 million in gross booking value and hosting more than 35,000 guests annually.

Behind CVP is Josh Hatter, a real estate investor and short-term rental operator who has been in the industry since 2012. He owns properties himself, operates a boutique hotel between Charleston and Savannah, and runs CVP across a complex multi-LLC structure with a fractional CFO in Phoenix and an external CPA managing the books. Josh has seen every tool, every trend, and every promise the STR industry has produced. He does not adopt software lightly.

CVP runs on a deliberate and battle-tested tech stack: Guesty as its property management system, QuickBooks Online for accounting, Amazon Business for purchasing, American Express for company spend, Breezeway for operations, RemoteLock for access, and Wheelhouse for pricing. Each tool earned its place. But for years, none of them talked to each other in any meaningful financial way. And that silence was expensive.

To understand how CVP got here, and what it took to fix it, you have to understand what fast growth actually costs when no one is watching the seams.

The Problem: Two Root Causes, One Expensive Outcome

Fast growth breaks things. Josh knows this better than most. CVP's trajectory through its Inc. 5000 years meant adding platforms, people, and processes quickly, often without stopping to audit whether any of it was actually working. By the time Josh took stock, CVP was running on 42 different platforms and spending over $300,000 a year on technology alone.

Two problems had been quietly compounding on each other. An expense process too broken to capture everything correctly, and a financial picture too incomplete to see what was being lost.

The Inefficiency Problem: An 8-Step Chain That Should Have Been One

Every expense CVP's field staff incurred followed the same broken path. An employee would make a purchase, scan the receipt, and post it to a dedicated Slack channel. From there, a Zapier automation pushed it to Airtable, where a finance virtual assistant would manually review and attempt to categorize each line item. A checker would review the VA's work. Another checker would review the first checker. Finally, the fractional CFO would reconcile everything at month-end.

Eight people and systems touched every single transaction before it was resolved. The process was slow, error-prone, and entirely dependent on every link in the chain doing their part correctly. Field employees dreaded it. The checker chain ground morale down. And the CFO was spending valuable time solving problems that should never have made it to her desk.

But the real cost of that broken process was not the time it wasted. It was what it made impossible to see.

The Invisibility Problem: You Cannot Fix What You Cannot See

When an expense process is too slow and too manual to capture everything correctly, the gaps it leaves behind become invisible. Cash leaks quietly. Vendor bloat goes unchallenged. And by the time anyone notices, the money is already gone.

That is exactly what was happening at CVP. Guesty, QuickBooks, Amazon Business, and American Express all operated in silos with no unified view of what was being spent, where, or by whom. Expenses were not just being billed late, some were never billed to property owners at all. One charge sat completely unaddressed from October all the way through to February before it finally appeared on an owner statement. The owner had a problem with it, and rightfully so.

Josh describes what the bloat had quietly become: "Our tech spend had gotten to over $300,000 a year. I'm embarrassed to admit that." Without a centralized view of spending, there was no way to see the full picture clearly enough to challenge it. Redundant platforms, inflated vendor contracts, and ongoing cash leakage were draining money month after month with no mechanism to catch any of it.

Where the Two Problems Collided

With the reconciliation chain moving slowly and no real-time visibility into spend, CVP's books could not close until 15 to 20 days into the following month. Josh was running a $10 million business on last month's data. Decisions about staffing, vendor contracts, and owner billing were all being made in the dark.

Owner relationships were beginning to feel the pressure too. Errors on statements, late charges, and missing documentation eroded the trust that keeps property owners on long-term contracts. CVP was growing quickly but bleeding quietly, and without visibility, there was no way to stop it.

The fix had to start at the source. And that meant finding a tool built specifically for the way STR operators actually work.

The Decision: The Only Software Josh Ever Chased Someone to Buy

The moment Josh recognized what Topkey could do did not happen in a sales meeting. It happened at lunch.

Josh watched a Topkey representative scan a receipt and noticed the per-property drop-down tagging. In seconds he understood exactly how it would work for a company like CVP. Property-level expense attribution at the point of purchase, by the person making the purchase, in real time. He knew immediately he needed it. By his own account, it is the only piece of software he has ever had to chase someone to buy.

CVP had used a competing expense tool before Topkey. The vision behind it was sound, but the execution could not keep pace with CVP's scale. Topkey was different. It was purpose-built for the short-term rental industry, not a generic business tool adapted after the fact. The difference was not vision. It was execution and integration depth.

Getting the team on board was not a challenge. Josh did not have to sell it internally. Once field staff saw it in practice, the argument made itself. As Josh puts it: "Once they see it in practice, being able to go to the store, incur that expense, and charge it to the owner right there, it just sells itself." The tool made life easier for the people actually incurring the expenses, not just the people trying to reconcile them afterward. Buy-in was immediate because the pain it solved was felt most by the people closest to it.

With the decision made and the team on board, the question was simple: what would CVP look like when the process finally worked the way it should?

The Solution: One Platform Pulling Everything Together

The root of both problems was the same. Expenses were not being captured correctly at the source, so nothing downstream could be trusted. Reconciliation was manual and slow because the data feeding it was incomplete. Visibility was impossible because the foundation it depended on was broken.

Topkey solved it in the right order. Fix the capture first. Everything else follows.

The Field Workflow That Changed Everything

The day-to-day experience for CVP's field staff changed completely.

An employee makes a purchase, scans the receipt in the store, and tags it to a specific property and owner before they leave. The process ends there. What used to require eight people and systems now requires one action by one person at the moment it happens.

No Slack channel. No Zapier automation. No Airtable row. No finance virtual assistant. No checker. No second checker. No CFO chase at month-end.

Expense ownership moved to the person with the most context, the one who made the purchase, at the moment they had the most information. That single shift solved the inefficiency problem at the source. And with the process fixed, the next problem began to solve itself.

Expense Capture That Stops Leakage Before It Starts

With every expense captured correctly at the point of purchase, the revenue leakage that had been draining CVP quietly for years had nowhere left to hide.

Before Topkey, expenses were falling out of the reconciliation chain at every stage. A receipt not posted to Slack in time. A Zapier automation that missed a transaction. A finance virtual assistant who could not determine which property an expense belonged to. By the time anything reached the CFO, money had already been lost. One charge sat unaddressed from October all the way to February. At scale, that kind of slippage accumulates fast.

Topkey closed that loop. Every transaction is captured, attributed to the right property and owner, and moving toward the correct statement in real time. There is nothing left to chase, nothing left to interpret, and no gap in the chain for revenue to leak through. And with the leakage stopped, something else became possible for the first time.

Real-Time Visibility Across All Spend

With expenses captured correctly and consistently, visibility became possible for the first time. Every dollar flowing through CVP, every platform, every vendor, every card, every transaction, visible in one place.

Josh could see not just individual expenses but patterns. Where bloat was hiding. Where leakage was happening. Where vendor contracts had quietly grown beyond what they were worth. That visibility became the foundation for every financial decision that followed, including the renegotiations and cuts that ultimately recovered $250,000.

But visibility alone was not enough. For it to mean anything, every tool CVP was already using had to feed into the same picture.

Integrations That Pulled It All Together

Topkey connected directly to the tools CVP was already running, removing the walls between systems that had made visibility impossible and reconciliation a manual exercise.

Guesty

CVP has run Guesty as their primary PMS since 2019 — it is the operational center of their business, handling everything from reservations to owner statements. The Topkey integration meant that expenses captured in the field could flow directly toward the right owner statement without any manual handoff between systems. What had previously required multiple steps, multiple people, and multiple opportunities for error now happened in a single connected workflow. For a company processing 35,000+ guest stays annually, that connection between financial operations and property management isn't a convenience — it's a requirement.

QuickBooks Online

Before Topkey, getting an expense from the field into QuickBooks was a multi-step ordeal. A field employee would incur an expense, scan the receipt, submit it to a dedicated Slack channel, which would then zap to Airtable, where a finance virtual assistant would manually categorize each item, which would then be reviewed by a checker, checked again by another person, before finally reaching the books at month-end.

As Josh described the transformation:

"With Topkey, we're able to skip all of that and kill all of that entirely. When somebody scans their receipt and it goes into Topkey, they can immediately attribute it to an owner's statement." (20:00)

Now, expenses are categorized at the point of purchase by the person who incurred them — the person with the highest likelihood of getting it right. The books receive a clean, organized handoff without duplicate entry, manual exports, or reconciliation work that should have been done weeks earlier.

American Express

Switching corporate cards was never on the table for CVP. With 80% of company spending running through their Delta American Express card and 1.1 million SkyMiles accumulated, the rewards equity built over years of business spending was too significant to walk away from.

Topkey connected directly to American Express and all external cards, meaning CVP kept their SkyMiles, kept their existing spending workflows, and gained full visibility into every transaction without changing how they spent. As Josh put it:

"I have atleast 1 million SkyMiles right now. I would say 80% of CVP spending is through the Delta Amex. We never pay for flights regardless of where we go." (17:00)

The ability to bring existing cards into Topkey rather than replacing them removed one of the most common adoption barriers in financial operations — the cost of switching.

Amazon Business

Before Topkey, visibility into Amazon Business purchases required individual user accounts for anyone on the finance team who needed to see what was being purchased and by whom. It was an access management problem layered on top of a reconciliation problem.

Topkey eliminated both. With the Amazon Business integration live, all purchasing activity flows directly into Topkey, attributed to the right property in real time. The finance team no longer needs separate Amazon logins to monitor spend.

Josh noted the immediate operational impact:

"We actually reduced the number of users that we had on Amazon as a result of the integration — because the finance contact can log in to Topkey and see all the expenses already attributed to a specific property. It just skips a step." (17:48)

Fewer accounts. Fewer logins. Fewer steps between a purchase and a properly attributed expense.

Breezeway

The Breezeway integration connected two parts of CVP's operation that had never communicated financially: field operations and finance. When a maintenance task or property expense originates in Breezeway, it flows through to Topkey without manual intervention — closing a gap that no other tool in CVP's stack had been able to fill.

For Josh, this is exactly what great software is supposed to do. Rather than trying to replicate what other platforms already do well, Topkey fills the specific niche that needed filling and integrates cleanly with everything else.

"I think it literally fills a niche that needs to be filled and integrates with everything else. There's not that many software platforms that you can say that about today." (29:09)

Every integration, every captured receipt, every tagged transaction was building something CVP had never had before: a complete, real-time picture of every dollar moving through the business. And once Josh could finally see everything clearly, he went to work..

Results: From Blind Spending to $250K Recovered

With every system connected and every dollar visible in real time for the first time, Josh didn't just have better software. He had leverage, and he used it.

The Visibility Audit That Unlocked Everything

Once Josh could see all of CVP's spend in real time, he did something he had never been able to do before. He built a full line-by-line sheet of every tech and vendor expense across the entire business and went through it systematically.

What he found had been hiding in plain sight for years. Redundant platforms no one was fully using. Vendor contracts that had grown beyond their original scope. Cash leaking through a reconciliation process too slow and too manual to catch everything. Josh went back to vendors and renegotiated contracts directly. He cut 17 of 42 platforms from CVP's tech stack. Each time he cut a platform, he asked the team the same question: did you notice anything different today? The answer, every time, was no.

Through spend reduction, vendor renegotiation, and leakage elimination, CVP recovered $250,000. Not from a single initiative or a lucky quarter. From finally being able to see everything clearly.

The Operational Wins That Compounded

The financial recovery was the headline, but the operational improvements compounded alongside it. Each one built on the last. Faster close times led to more accurate statements, more accurate statements led to less owner friction, and less owner friction meant the team could focus on growth instead of damage control.

Month-End Close Is 40% Faster

Before Topkey, closing the books was a multi-week exercise in chasing context that should have been captured weeks earlier. Expenses incurred in October would surface in February. The reconciliation chain was so long and so manual that by the time everything reached the books, the month it belonged to was long gone.

With expenses captured and categorized at the point of purchase, the downstream reconciliation process has nothing left to chase. The person who incurred the expense, the person with the most accurate knowledge of what it was for and which property it belonged to, handles the attribution immediately. By the time it reaches the finance team, the work is already done. Books close on time, owners receive accurate statements promptly, and the team is no longer firefighting problems that originated in the field weeks earlier.

8 Steps Collapsed to 1

The reconciliation workflow that once required a receipt to travel through Slack, Airtable, a finance virtual assistant, a checker, and another checker before reaching the books now takes a single action at the point of purchase. Josh described the old process in detail:

"Somebody would incur an expense, get the receipt, scan it, submit it to Slack in our expense channel, which would zap to Airtable, and then our finance virtual assistant would have to go through every single item to figure out what it needed to be billed to. Then there was a person that worked for my CFO that would check the checker, ultimately leading to the CFO to reconcile those books every month." (20:00)

With Topkey, that entire chain is gone. One step. One person. Done at the moment of purchase.

A Team That No Longer Dreads It

Nobody, not the CEO, not the field staff, not the finance team, enjoys chasing receipts. It is the part of the job that has to get done, that everyone knows has to get done, and that everyone quietly resents. At CVP, that frustration had been baked into the monthly routine for years.

What changed with Topkey wasn't just the process. It was how people felt about it. Because the platform puts the responsibility on the person incurring the expense, in the moment, at the point of purchase, before the context is lost, it removed the retroactive burden that made the work so draining in the first place.

Josh didn't hear about the shift in a report. He heard it directly, unsolicited, from someone who never brings good news to the CEO. A staff member who had always hated this part of his job told Josh he didn't hate it anymore. As Josh put it, nobody comes to the CEO with good news, so hearing something like that unprompted was, in his words, "a massive compliment for a piece of software." (22:04)

Revenue Leakage Stopped

The gap between when an expense is incurred and when it gets billed to an owner is where leakage lives, and CVP had been living with that gap for years. An expense incurred in October that didn't surface until February wasn't just a billing problem. It was an owner relationship problem. Going back to a homeowner months after the fact with a charge they had no visibility into created friction that eroded trust, and in a business where owner retention is everything, that friction compounds quickly.

With Topkey, expenses are captured at the point of purchase, attributed to the right property immediately, and billed in the same month they are incurred. As Josh noted, there are far fewer issues today than there were six months ago. homeowner months after the fact with a charge they had no visibility into created friction that eroded trust and reflected poorly on the operation. In a business where owner retention is everything, that friction has a cost that goes far beyond the dollar amount on the invoice.

Owner Satisfaction Rebuilt

Owner statement errors don't just create administrative work. They create doubt. When an owner sees a charge they don't recognize, or receives a bill months after an expense was incurred, their confidence in the management company takes a hit that is difficult to recover from.

CVP had approximately 60 clients at the time of implementing Topkey. The reduction in owner statement friction has been significant, and Josh believes the operation is on track to reach near-perfect accuracy.

"I would say that reduced the friction by at least 80%. And I think we can actually get to 98%, where there's maybe one question a month out of 60 clients." (21:09)

Fewer errors. Fewer questions. Fewer conversations that should never have been necessary in the first place.

The results CVP achieved did not happen by accident. They happened because Topkey was built for the specific way this industry works.

Built for the Field, Not Just the Back Office

What makes Topkey different from generic expense management tools is where it solves the problem. Most tools address the back office. Topkey addresses the moment the expense happens.

By pushing ownership to the person incurring the cost, the person with the most context and the highest likelihood of getting the categorization right, Topkey eliminates the need for checkers, chasers, and reconcilers downstream. The process does not need to be audited and corrected at month-end because it is done correctly at the point of purchase.

Josh is direct about why this matters for STR operators evaluating their options: "It really is set up specifically for this industry. It makes the person on the front lines incurring those expenses, their life is so much easier."

Property-level attribution, owner statement integration, and PMS connectivity are not features bolted onto a general business tool. They are native to how Topkey was designed. And it works across the cards and platforms operators are already using, no forced card switching, no new workflows built from scratch.

For Josh, the results CVP achieved were not just proof that Topkey worked. They were proof that the infrastructure could hold as CVP continued to grow.

Scale Confidence: A Core Platform for the Next Three Years

CVP is growing again. After a deliberate consolidation phase in Q3 and Q4, Josh is leaning back into expansion, targeting properties that gross between $300,000 and $800,000 in individual rental revenue. The infrastructure supporting that growth needs to hold.

Topkey is part of that foundation. Josh places it among the five core systems powering CVP's $10 million business, alongside Guesty, Breezeway, RemoteLock, and Wheelhouse. As he puts it: "We would put this in the core five systems that are the backbone of our $10 million business and growing."

That level of conviction from a three-time Inc. 5000 operator who has been in the STR industry for over a decade says more than any feature list could.

The Lesson for Every Scaling STR Operator

The two problems CVP faced were never separate. Inefficiency created the invisibility. When your expense process is too slow and too manual to capture everything correctly, the gaps it leaves behind become impossible to see. Cash leaks quietly. Vendor bloat goes unchallenged. And by the time anyone notices, the money is already gone.

That is the cycle Topkey broke. Fix the capture, and visibility takes care of itself. And once you can see everything, the decisions make themselves.

The $250,000 CVP recovered did not come from working harder. It came from finally being able to see clearly.

You cannot cut what you cannot see. You cannot fix what you cannot track. You cannot bill what you cannot capture.

See what Topkey's visibility can do for your operation. Schedule a demo today.