How Upkey Streamlined Owner Financial Reporting with Topkey

When Raina Strampello joined Upkey in 2019, the company was just beginning its growth journey. What started as her brother listing his own home on Airbnb had evolved into a small but growing vacation rental management business. 

With Raina's background in bookkeeping, tax preparation, and accounts receivable at companies like H&R Block, she was naturally drawn to handling Upkey's financial operations. Today, Upkey manages 40 vacation rental properties across their region, with plans to continue scaling. 

The Challenge: Manual Financial Tracking and Limited Visibility

As the company expanded from a handful of properties to dozens, their financial systems struggled to keep pace.

"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," explains Raina. "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."

This manual approach created several significant challenges:

Inefficient Owner Expense Tracking

Before Topkey, Upkey's expense management process was labor-intensive and vulnerable to errors. The team would save invoices to their Google Drive, manually categorize them by property, and then perform calculations to determine what to bill to which owners.

Before implementing Guesty in 2022, their process was even more manual, relying exclusively on spreadsheets and manual calculations.

Time-Consuming Month-End Close

The end of each month brought significant stress to the Upkey team as they dedicated significant time to compiling accurate owner statements.

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

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."

Limited Financial Analysis

Perhaps most concerning was Upkey's inability to properly analyze their spending patterns and profitability across properties. Without proper categorization and reporting tools, they couldn't easily identify trends or make data-driven decisions.

The Solution: Implementing Topkey's Financial Operations Platform

After struggling with these challenges, Upkey implemented Topkey to transform its financial operations. The decision came after exploring various options for streamlining their increasingly complex financial processes. What impressed Raina most was Topkey's ability to consolidate all aspects of their financial operations into one cohesive system.

"It revolutionized our flow and our statements and the way that we do our bookkeeping," Raina explains. "We're so glad it's a part of our tech stack."

With Topkey, Upkey gained a comprehensive platform that integrated directly with their existing systems, including Guesty and QuickBooks. This integration created a seamless flow for expense tracking, owner billing, and financial reporting. The platform's purpose-built features for vacation rental managers meant they didn't need to cobble together multiple generic solutions or create complex workarounds.

Real-Time Expense Tracking

One of the most significant improvements came from Topkey's ability to track expenses in real-time. Instead of letting receipts and transactions pile up until month-end, Raina now processes them daily. 

This shift from batch processing to continuous management has fundamentally changed how Upkey handles its finances. The team no longer faces the dreaded month-end crunch that previously consumed entire days of work. 

Instead, with just minutes of daily attention, expenses are properly categorized, receipts are attached, and owner charges are processed—creating a steady, manageable workflow that prevents backlogs from forming. This proactive approach has ripple effects throughout the entire operation, reducing stress and improving accuracy.

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

Streamlined Owner Billing

The ability to easily categorize expenses and push them to owner statements has eliminated many of the headaches associated with monthly owner reporting. 

Before Topkey, Upkey's team would struggle with manually calculating charges, often combining multiple receipts into single entries and attaching documentation in ways that were difficult for owners to interpret. This created confusion and sometimes led to questions or disputes from property owners. 

With Topkey, each expense is individually tracked, properly categorized, and automatically flows to the correct property with all supporting documentation. This granular level of detail provides unprecedented transparency to owners while requiring less work from the Upkey team.

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

Efficient Amazon Purchase Tracking

As a company that frequently orders supplies from Amazon, Upkey particularly appreciated Topkey's Amazon integration feature. 

This integration solved a persistent challenge for the team, who previously struggled to match Amazon's often fragmented shipments and charges to specific properties. With multiple items shipping from different warehouses, a single purchase could generate several separate credit card transactions, creating reconciliation headaches. 

The integration allowed Upkey to implement a simple system where purchase order numbers identify the property during checkout, and Topkey automatically matches and categorizes the resulting transactions—eliminating hours of manual matching work.

"The Amazon integration - it is wonderful to not have to do the guesswork," Raina enthuses. "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 Credit Cards and Banking

Topkey's integrated credit cards and banking solutions 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.”

Bulk Owner Payments

Another feature that significantly improved Upkey's efficiency was Topkey's bulk owner payment capability. 

Processing payments to dozens of property owners had previously been a time-consuming and error-prone process. The team would manually transfer data between systems, copying and pasting amounts from their property management system to their banking platform—a method that introduced opportunities for mistakes with each transaction. 

With Topkey, this entire process has been streamlined into a simple CSV upload that handles multiple payments at once. The accuracy and speed of this process not only saves time but also improves owner satisfaction through consistently timely and correct payments.

"Bulk owner payments are so time-saving," Raina explains. "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."

Seamless Guesty Integration

Upkey's technology stack revolves around Guesty as their primary property management system, making the Topkey-Guesty integration a crucial component of their financial workflow. Topkey’s integration to Guesty creates a seamless data flow between the two platforms, eliminating the double-entry problems that previously plagued their operations. 

Before Topkey, Raina would manually transfer expense data from spreadsheets into Guesty, a process that was both time-consuming and error-prone. Now, expenses tracked in Topkey automatically sync to Guesty, creating owner charges that appear on statements with all supporting documentation attached.

 This integration was particularly valuable for Upkey's weekly team meetings, where they analyze property expenses and make data-driven decisions about supply management and maintenance budgets. The unified system means everyone is working from the same accurate data, whether they're handling day-to-day operations in Guesty or financial management in Topkey.

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

The Results: Transformed Financial Operations and Business Growth

After implementing Topkey, Upkey experienced significant improvements across its financial operations, leading to better owner relationships, increased efficiency, and a stronger foundation for growth.

Dramatic Time Savings

The efficiency gains from Topkey have been substantial, freeing up significant time that was previously spent on manual reconciliation.

"I'm saving easily five hours a week on average because it would take me a week to get ready for owner statements," Raina calculates. "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."

This time savings has allowed Raina to focus on more strategic aspects of the business, including refining systems, improving team communications, and supporting growth initiatives.

"I'm now able to refine our systems and our communications," she explains. "I'm able to have a little bit more of an administrative type role with our team and getting our team systems together."

Improved Owner Relationships

Perhaps the most noticeable improvement has been in Upkey's relationships with property owners. The clear, detailed expense reporting has eliminated questions and disputes about charges.

"We have not heard a peep in months and months about anything that has to do with our expense reporting," Raina states proudly. "It's been great because the information is right there. It's accurate and I'm able to put in really nice descriptions."

This transparency has strengthened owner trust and reduced the administrative burden of responding to owner inquiries.

Enhanced Financial Visibility

With Topkey, Upkey now has unprecedented visibility into its financial operations. The ability to analyze expenses by property, vendor, or category has transformed their decision-making process. This visibility extends to their weekly supply deep dive meetings, where they can now easily track and analyze expenses across properties.

"When we have our supplies deep dive, we're able to go right into Topkey and see every property," explains Raina. "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?'"

Cost-Effective Implementation

Perhaps most impressive is that the benefits of Topkey have come with minimal additional cost to Upkey. The interest earned on their bank accounts* and credit card rewards have effectively offset the cost of the platform.¹

"What it costs to have Topkey and what we're getting in interest charges is huge," Raina shares.² "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 streamlined and efficient, Upkey has built a foundation that will support its ambitious growth plans.

"We would not have been able to grow in the way that we are growing now," Raina states. "Our structures are in place and we're confident about them."

This confidence has allowed them to take on more properties and even bring in an operations manager to support continued expansion. Their long-term plans include growing their vacation rental portfolio and potentially adding a boutique hotel.

"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." Raina shares.

Why Topkey: Industry-Specific Solutions and Exceptional Support

For Upkey, what sets Topkey apart is not just its comprehensive features but its deep understanding of the vacation rental industry and commitment to customer success.

"Topkey is leading the industry in short-term rental banking software," Raina believes. This industry-specific focus has been crucial in addressing the unique challenges faced by vacation rental managers.

The support provided by Topkey's customer service team has been instrumental in Upkey's successful implementation and ongoing use of the platform.

"The CS team has been amazing. They are patient, they have an answer for every question," Raina emphasizes. "They have really helped with our procedures and framework. We didn't know that we could grow this way."

This combination of industry-specific features and exceptional support has made Topkey an essential part of Upkey's technology stack and growth strategy.

"If we could, we'd just scream it from the mountaintops to use Topkey, it will help bring structure and flow and accuracy to your business," Raina concludes.

Looking Ahead: A Foundation for Sustainable Growth

As Upkey continues to expand its vacation rental portfolio and potentially diversify into boutique hotels, they see Topkey as a vital partner in their journey.

"We're going to go all the way with Topkey," Raina affirms. "I see Topkey continuing to improve all of its features, which has been so great. I feel like we're growing together, and that is a wonderful feeling."

This mutual growth has created a foundation for what Raina describes as "a perfect relationship" – one that will support Upkey's ambitions while ensuring their financial operations remain streamlined, accurate, and efficient.

Ready to transform your vacation rental company's financial operations? Schedule a demo with Topkey today to learn how we can help automate and improve your financial processes.

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*Topkey is a financial technology company and is not a bank. Banking services provided by Thread Bank; Member FDIC. The Topkey Visa Debit & Charge Cards are issued by Thread Bank pursuant to a license from Visa U.S.A. Inc. and may be used everywhere Visa cards are accepted.

1 | Terms and conditions apply to the charge card rewards program. To redeem your Points Rewards, you must email us at support@topkey.io and provide the name of the Account holder with your request to redeem your Points Rewards. You may redeem your Points Rewards only if you are not delinquent in any amounts then owed to Topkey. The purchase of money orders or cash equivalents, and account funding made with your charge card are not eligible for charge card rewards.  Please refer to the Topkey Charge Card Rewards Terms and Conditions.

2 | The interest rate on the High Yield Deposit Account will be 3.31% with an Annual Percentage Yield (APY) of 3.36%. The interest rate on the Regular Deposit Account will be 1.71% with an Annual Percentage Yield (APY) of 1.72%. These rates are effective as of 12/19/2024. These are variable rates and are subject to change after the accounts are opened based on the Federal Funds Rate. Minimum opening deposit and average balance requirements may apply. Fees could affect earnings on the account.

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