How Upkey Saves 100+ Hours a Month with Topkey

When Raina Strampello joined Upkey in 2019, what began as her brother listing his own home on Airbnb had grown into a small but expanding vacation rental business. With a background in bookkeeping, tax preparation, and accounts receivable, she was the natural person to take on the company's finances.

Running Guesty as their property management system and QuickBooks Online for accounting, Upkey had the right tools to manage a growing portfolio. The financial work holding it all together, though, still ran on spreadsheets, saved invoices, and a lot of manual math.

Two years into partnering with Topkey, that work looks nothing like it used to. Today, Upkey manages around 40+ properties across North Florida with a financial operating system that saves the team more than 100 hours every month, gives them confidence that every owner statement and OTA payout is accurate, and has helped them build a leaner, more profitable business.

The Challenge: Growing Faster Than the Tools Could Keep Up

As Upkey grew from a handful of units to dozens, the team was doing everything right with the tools that existed. The problem was that the tools they used handled parts of the job, but none were designed for the unique financial workflows of a growing short-term rental business. Careful, organized work was still slow work, and it was starting to consume the people doing it.

Tracking Every Expense by Hand

Before Topkey, Upkey's expense process was thorough but manual. The team saved invoices to Google Drive, categorized them by property, and worked out what to bill to which owner by hand.

"We kept a spreadsheet to track our charges, and we would save invoices to our drive, and then we had to audit it by property," Raina explains. "We had to be really organized to get it right. I'd be on my phone using the calculator, trying to combine charges so that we could put them in Guesty."

The system worked because the team made it work, not because anything was built to do it for them.

No Way to Verify OTA Payouts

Expenses weren't the only financial blind spot. Upkey also had no practical way to verify that payouts from Airbnb, Booking.com, and VRBO matched what they had actually earned.

"We trusted that the Airbnb deposits were correct. We trusted that the Booking.com deposits were correct. We trusted that the VRBO deposits were correct," Raina says. "It was just nebulous and crossing our fingers hoping that it was okay."

Without a way to reconcile reservations against OTA payouts, the team couldn't confidently identify cash leakage or verify they were collecting every dollar they were owed.

"There wasn't anything out there that could solve the problem."

Time-Consuming Month-End Close

Every month ended the same way: with hours of manual work to verify owner statements before they could be sent.

"At the end of the month, it was hours and hours of work to try to verify that we were accurate with our charges," Raina recalls.

Charges were often grouped into a single owner statement entry with multiple receipts attached, making statements harder for owners to understand and requiring extra time to verify every calculation before they went out.

Owner Communication Challenges

The manual process also affected their relationships with property owners. Without a streamlined way to attach receipts and document expenses, owners could question charges on their statements. Upkey avoided this problem by spending excessive time on manual work.

"They would have questions because we would do charges as one entry and then attach 10 receipts," says Raina. "If I had an inaccurate entry or my math wasn't right... it was an issue for us."

The Solution: One Connected Financial Operation

Upkey brought on Topkey to connect the financial workflows that had previously lived across spreadsheets, disconnected systems, and manual processes.

Instead of juggling separate tools to manage expenses, owner billing, payments, banking, and revenue verification, the team could manage those workflows in one place while continuing to use Guesty and QuickBooks Online.

Getting there was hands-on, and Raina is the first to say the support is what made it stick.

"At the beginning I was a little apprehensive," she recalls. "I'm not the most tech savvy. Thank God you guys have such good service.”

Over the past two years, as Topkey has expanded its platform, Upkey has continued refining its financial processes alongside it. What began with expense management has grown into a connected financial operation that now supports nearly every part of the business.

Real-Time Expense Tracking

One of the biggest changes was moving away from the month-end rush. Instead of letting receipts and transactions pile up, Raina now processes expenses daily in Topkey.

"It's something I maintain every day, which wasn't part of my flow before using Topkey," she says. "I just go in every day, classify our transactions, push the owner charges. And it's done. It makes my life so much easier."

Each expense is tracked individually, categorized, and assigned to the correct property with its receipt attached. That gives owners clearer documentation while preventing the backlog of manual work that previously built up at the end of each month.

Accurate Revenue Reconciliation

Before Topkey revenue reconciliation, Upkey had no consistent way to verify that booking revenue matched the deposits coming into the business. Raina could review some activity in Stripe, but there was no reliable way to reconcile reservations across Airbnb, Booking.com, VRBO, Guesty, and payment processors.

Before Topkey, Raina says the team could only piece together parts of the process in Stripe and otherwise had to trust the deposits were correct.

Today, that process is automatic. Topkey brings together booking revenue and deposit data from OTAs, Guesty, and payment processors, allowing Raina to review reservations and quickly confirm that what was booked matches what was received instead of manually piecing information together across multiple systems.

"To see these transactions just match up so beautifully has been a game changer for us," she says.

Instead of wondering whether deposits are correct, Raina now has confidence that the business is collecting what it has earned. If something doesn't match, she can identify it quickly before it turns into cash leakage or a larger accounting issue.

Efficient Amazon Purchase Tracking

Upkey frequently orders supplies from Amazon, where a single purchase can be split into multiple shipments and separate card charges. Before Topkey, matching those charges back to the correct property required additional research and manual work.

With Topkey's Amazon Business integration, the team adds a purchase order number during checkout to identify the property. Topkey then imports the order information and organizes the resulting charges, removing much of the guesswork from the process.

"The Amazon integration is wonderful to not have to do the guesswork," Raina says. "Just put in a PO on Amazon when you're making the purchase, and it all shows up by charge. All you have to do is push the owner charge, and it's just awesome."

Integrated Cards* and Banking*

Topkey's integrated charge cards* and banking* platform gave Upkey unprecedented control over its finances. The ability to create and assign cards to team members, track expenses in real-time, and earn rewards has transformed their financial operations.

This integration has been particularly valuable for managing their maintenance team's expenses. Previously, tracking purchases made during property visits required collecting physical receipts from team members—a process that was inconsistent at best.

Now, maintenance staff receive automatic text notifications after making purchases, prompting them to immediately capture receipts and assign them to the correct property. This real-time capture ensures nothing falls through the cracks, while the centralized management of all cards gives Upkey's leadership full visibility into spending patterns.

"When we add team members, being able to go in directly to our bank and create a new card, assign it to them, put their name on it, it's wonderful," says Raina. "For our team members who make in-person purchases, the ability to instantly upload receipts from a text notification has been huge. It's been great."

Streamlined Owner Billing

Topkey also simplified how Upkey turns property expenses into owner charges. Instead of combining multiple purchases into one entry and attaching a stack of receipts, the team can track each charge individually and send it to the correct property with its documentation attached.

"Being able to split by property and push it so easily to the owner statements is big," Raina says. "And then the receipts just go right over. It's awesome."

This creates clearer owner statements while reducing the time Upkey spends calculating charges, organizing receipts, and responding to questions.

Bulk Owner Payments

Paying dozens of owners previously required Upkey to move amounts between systems manually, copying and pasting payment information one owner at a time.

Topkey's bulk owner payment capability replaced that process with a single CSV upload, allowing the team to prepare multiple accurate payments at once.

"Bulk owner payments are so time-saving," Raina says. "It gives so much relief that we can just load up a CSV and get accurate amounts in there. It used to be so funky going from one program to the other program and transferring the amounts, copying and pasting."

The simpler workflow saves time and reduces the opportunity for mistakes when transferring payment information.

Connected Guesty Workflow

Guesty remains central to how Upkey manages its properties, so the connection between Topkey, Guesty, and QuickBooks Online is an important part of the financial workflow.

Before Topkey, Raina transferred expense information from spreadsheets into Guesty manually. Now, expenses categorized in Topkey can be pushed into Guesty as owner charges with the related documentation attached.

"It's so much easier to create owner charges in Topkey and be accurate," Raina says.

The same financial information can then flow into QuickBooks Online, reducing duplicate entry and helping the team work from a more consistent view of expenses, owner charges, and accounting activity.

The Results: A Financial Operation That Runs More Efficiently

Two years in, the change shows up less as a feature list and more as a different way the company operates. The work got smaller, the team became more efficient, owner relationships improved, and the business became more profitable.

100+ Hours a Month Back Across the Team

The time savings did not stop at Raina's desk, which is the part that surprised even her. Asked how many hours the whole team gets back, Raina didn't hesitate: "Easily a hundred hours a month. Easily."

Her own week is the clearest example. What used to take a week of prep now takes about half an hour a day. "I seem to only put in about half an hour a day doing my Topkey transactions and checking my bank balance. It's instant and wonderful," she says.

One assistant now owns receipt capture for the units, Raina reviews and pushes owner charges, and the entire workflow keeps moving without anyone dreading month-end.

That reclaimed time goes right back into the business. "I'm now able to refine our systems and our communications," Raina says. Instead of spending time chasing receipts and reconciling transactions, the team is focused on improving operations and supporting continued growth.

2x More Profit From Running Leaner

With the financial operation running more efficiently, the numbers moved in the right direction. Between eliminating cash leakage, capturing expenses more accurately, applying markups consistently, and giving the team back valuable time, Upkey significantly improved its bottom line.

"Our books are showing easily double the profit," Raina says. She credits the combination of stronger financial controls and a leaner operation: "I pull the numbers together every month and I just shake my head. I can't believe we're doing this. We've figured out how to run so much more leanly."

Improved Owner Relationships

The old owner statement process invited questions because combined entries and stacks of receipts were hard to follow. Today, every expense is itemized, assigned to the correct property, and backed by its receipt, giving owners the transparency they expect.

"I never hear from owners anymore. It doesn't happen," Raina says. Months go by without a single question about an owner statement because the information is accurate, easy to follow, and supported with the right documentation.

That transparency has strengthened owner trust while eliminating another time-consuming administrative task for the Upkey team.

Enhanced Financial Visibility

Topkey has given Upkey a clearer picture of its financial operation. With Topkey revenue reconciliation, the team no longer has to rely on multiple systems and manual checks to verify booking revenue. Instead, they can confidently reconcile revenue against deposits while also having complete visibility into expenses across every property.

That visibility extends beyond month-end reporting. During weekly supply reviews, the team can quickly analyze spending by property, answer owner questions with confidence, and identify opportunities to improve operations.

"When we have our supplies deep dive, we're able to go right into Topkey and see every property," Raina explains. "This has been huge because the owners used to give us pushback on 'Oh, you've ordered too many supplies' or 'What's the deal with this supply?'"

From revenue reconciliation to property-level expense reporting, Upkey now spends less time searching for answers and more time making informed business decisions with confidence in its financial data.

Cost-Effective Implementation

Perhaps most impressive is that the benefits of Topkey have come with minimal additional cost to Upkey. The interest¹ earned on their bank accounts* and credit card* rewards have effectively offset the cost of the platform.

"What it costs to have Topkey and what we're getting in interest¹ is huge," Raina shares. "That makes it a no-brainer for us."

When asked to quantify the savings, she estimates: "I would say we are saving thousands. We're also saving at least a thousand a month on the excess inefficiency that does not exist any longer."

Scalable Foundation for Growth

With its financial operations now connected and efficient, Upkey has built a foundation for sustainable growth. Instead of adding complexity as the business evolves, the team has confidence that its financial processes can scale alongside it.

That confidence allows Upkey to focus on refining its operations, strengthening its portfolio, and continuing to grow without worrying that the financial side of the business will fall behind.

Why Topkey: A Partner That Grows With You

For Raina, what sets Topkey apart isn't a single feature. It's that the platform continues to evolve alongside the short-term rental industry while giving customers a team that is invested in their success.

Over the past two years, Raina's view of Topkey has changed. What started as an expense management tool has become the foundation of Upkey's financial operation. Today, she builds her financial workflows around Topkey.

One thing Raina appreciates most is how quickly customer feedback turns into product improvements. She remembers asking for a better way to search deposit accounts during a customer call. By the next day, the feature had already been built and released. It's one of many reasons she feels like Topkey is building the product with its customers, not just for them.

For Raina, that combination of continuous innovation and hands-on support is what makes Topkey different. "You take this great software, and you couple it with outstanding support from Topkey, and you have a product that's just undeniable for a manager."

Looking Ahead: Built for the Future

For Upkey, the biggest change was building a financial operation that could support the business for years to come.

What started as a way to simplify expense management has become the foundation of how the team manages expenses, reconciles revenue, pays owners, and makes financial decisions with confidence. Instead of relying on spreadsheets and manual work, Upkey now has a connected financial operation that scales alongside the business.

As the company continues growing its portfolio of premium vacation rentals, Raina is confident that the foundation will continue to support them.

"We're going to go all the way with Topkey," she says. "I feel like we're growing together, and that is a wonderful feeling."

For Upkey, the biggest transformation wasn't just saving more than 100 hours a month. It was building a financial operation that helped the business run leaner, eliminate cash leakage, and ultimately double its profit.

Every short-term rental operator's business is different, but the challenges are often the same. Book a demo to see how Topkey can help you build a more connected, profitable financial operation.