Sierra Alderman is the founder and CEO of Host My Home, a hospitality company managing 85 vacation rentals across the Virginia Beach coastal area, Norfolk, and Portsmouth, with a handful more in Florida and Georgia. The operation runs on Hospitable as its PMS and QuickBooks Online for accounting, but for years the financial work connecting the two ran on chasing, memory, and Google Sheets. What was manageable at 30 properties had clearly broken by 60. With Topkey, Sierra cut five days from her month-end close and got her focus back on growing the business.

The Challenge: The System That Broke Between 30 and 85 Properties

Host My Home grew the way most successful vacation rental companies do: property by property, with the financial process patched together behind the scenes. Every stage of growth added transactions, vendors, and cards. None of it added structure.

Receipts everywhere, money slipping away

Host My Home runs a field-heavy team, including quality assurance inspectors the company calls runners, who buy what properties need as they move through them. So many team members carried credit cards that every month meant "chasing them down asking what was this, where do you have it, where are you submitting it," as Sierra puts it.

She tried several receipt apps and hit the limits of each one. Eventually her bookkeeper gave up and asked to just drop everything into Google Drive, which meant charges got resolved over email, one question at a time.

The cost of that chaos surfaced long after anyone could fix it. "It's months later, and I'm trying to figure out, where's this $25 Walmart? We have no idea," Sierra recalls. Multiply one mystery charge across 85 properties and the damage adds up: by her own estimate, roughly 10% of expenses that should have been billed to owners never made it onto a statement.

Bill pay all over the map

Paying vendors had no system at all. It had workarounds. "If we had one vendor that did Square, we would open it and put our credit card in there," Sierra says. "Or some of them we would write checks, or some of them we would do through QuickBooks." Venmo filled in the gaps.

The costs stacked up in quieter ways too. QuickBooks charged roughly $7 per month for every vendor kept active for online payment, so the cost of paying people grew right alongside the vendor list.

The work itself landed on the operations manager, whose Mondays disappeared into bill pay entirely. At 40 properties it took a few hours a week. At 85, Sierra recalls her operations manager saying, "you really need a whole position for this."

Hospitable and QuickBooks Online, not connected

The tools themselves weren't the problem. Hospitable ran the properties and QuickBooks Online held the books, but nothing connected them. Every new property meant another round of manual setup, and every charge had to be matched to a property by hand and typed into a memo for whoever touched the books next to decode.

The bookkeeper fell behind on class tracking in QuickBooks, and card and vendor charges were the hardest part: getting them organized, then assigned to the correct property, one at a time. With no bridge between the two systems, month-end arrived as a pile of uncategorized transactions.

A month-end that swallowed the founder

All of it came due at month-end. Closing the books took four to seven days, around 40 hours of work, with a solo contract bookkeeper stressed for a week straight trying to organize card charges and assign them to the right properties.

Sierra was pulled in just as deep. "I couldn't do pretty much any other work," she says. "For four days I was just reviewing reports and chasing down receipts."

No safe way to hand it off

Approving charges had always been Sierra's job. She'd read through the reports, remember that a plumber had been out to a property, and go back and forth with the bookkeeper to get charges where they belonged.

Delegating didn't work either. The bookkeeping sat with one contractor, and it was simply too much for one person to keep up with. Handing bill pay to the operations manager just consumed her role instead. The process wasn't structured enough for anyone to succeed with it, so everything flowed back to the founder.

By the time Sierra walked into VRMA in October, she wasn't browsing the exhibit hall. She was hunting for a fix. That's when she found Topkey.

The Solution: Financial Operations Built for Vacation Rental Operators

Topkey pulled it all into one place. Receipts that lived in Google Drive, a close that lived in Google Sheets, and payments scattered everywhere now run through a single system.

Stopping leakage where it starts: in the field

Receipt chasing, automated

The receipt workflow was the feature that first sold Sierra on Topkey, and it's the one her field team feels most. Receipt automations took over the follow-up work her team used to do by hand. Runners text their receipts in, and Topkey sends the reminders when something is missing. "They'll text the receipts and they'll bug them for us," Sierra says. "That was just huge."

That one workflow ended the monthly interrogation. Nobody in the office keeps a list of who owes receipts, because the system keeps it for them. Receipts arrive with a property attached while the purchase is still fresh, not months later as a mystery line item.

Every charge tagged to a property from a dropdown

Before Topkey, connecting a purchase to a property meant typing out a memo at the register and hoping someone could decode it at month-end. With Topkey expense management, runners assign each purchase to a property from a dropdown at the point of sale instead.

That one change moved the accounting work from the back office to the moment of purchase. The charge for that new fridge lands on the right property while the runner is still in the store, not in an email thread three weeks later. For a company spread across 85 properties in three states, the property-level detail that used to leak away now captures itself.

Amazon orders that categorize themselves

Supply ordering runs through Amazon at volume in a portfolio this size, and it used to be one more pile to sort at month-end. Through the Amazon Business integration, those orders now come into Topkey already categorized.

Sierra doesn't think much about it anymore, which is the point. The orders arrive tagged, the books stay clean, and one of the highest-volume expense sources in the business stopped generating questions.

Bill pay in one place, one run a week

From payment sprawl to one weekly batch

Changing how they paid bills took some convincing. Sierra's operations manager knew exactly how each vendor got paid and didn't want to mess with her system, but that system only held together because of the manual work she poured into it every week.

Sierra's pitch was to walk her through how much easier one system would be: instead of logging into Square for one vendor, writing a check for another, and paying a third through QuickBooks, every bill lands in Topkey bill pay. Bills queue up during the week, and on payment day she reviews the list and sends everything out at once in one batch. No juggling logins, no remembering which vendor gets paid which way.

The skepticism didn't last. "She called me recently and she was like, you were right, I love it. It's so much of a time saver," Sierra says. With every vendor finally loaded in, the weekly run is quick enough that Sierra describes it in sound effects: "It's so nice now, just like, boop, boop, boop."

Host My Home also changed the rules of the game with its vendors: payments go out once a week now, not whenever a bill happened to arrive. One cadence, one batch, one place to see what's been paid.

Vendors onboard themselves, checks still an option

Getting a vendor set up used to mean collecting payment details and tax forms by hand, vendor by vendor. Now new vendors submit their ACH details and W-9 through Topkey's vendor onboarding, so the paperwork is done before the first bill is due.

Not everyone wants ACH, and that's fine. For the vendors and owners who still want an old-school check, Topkey sends those too, from the same place as everything else.

Ending double-entry: Hospitable and QuickBooks Online connected

Hospitable: new properties flow in on their own

Host My Home adds properties regularly, and each one used to mean another round of manual setup in every system. Now every new property added in Hospitable pulls into Topkey automatically, ready for expense tagging from day one. "It's fantastic having new properties pull in already and not have to deal with another step," Sierra says.

Small things like that compound at 85 units: nothing gets typed twice, so nothing gets typed wrong. The property list in Topkey always matches the property list in the PMS, which means the field team's dropdown is never out of date and the record keeping holds up on the accounting side.

QuickBooks Online: clean data where the books live

Transactions sync from Topkey into QuickBooks Online with properties already assigned, so the books are built on clean, current data instead of a month-old pile of questions. The bookkeeping now starts organized instead of starting over.

The month-end reports that used to depend on Sierra's memory now depend on data that was captured correctly the first time. The books stay current through the month instead of being reconstructed at the end of it.

A back office the founder could finally hand off

The structure Topkey added made delegation safe for the first time. Host My Home brought on a controller who now pays the bills, runs payroll, works in Topkey monthly to keep reports on track, and catches the plumber invoice that landed on the wrong statement before it goes out.

Sierra keeps the final level of review and nothing else. As she puts it, that alone should save her quite a few hours each month.

The Results: From Accounting Nightmare to a Repeatable Close

Five days back every month

Month-end used to mean four to seven days of grinding: reports, receipt chases, and follow-ups stretching across the week, around 40 hours in all.

Now the close runs through a system instead of a scramble. Receipts arrive on time, expenses arrive tagged, and the controller works from organized data rather than a pile of unknowns.

Sierra expects her part of month-end to soon take two hours at most. For a founder who used to lose four days a month, that's a different job description.

The 10% that stopped slipping away

Before Topkey, leakage was invisible until it was too late to fix. Charges sat uncategorized, statements went out incomplete, and by Sierra's estimate about 10% of owner billables were never collected.

Now every charge is tied to a property the moment it happens, so owner statements reflect what was actually spent. "We finally have a scalable system that we can repeatedly do monthly that's not random," Sierra says. "I felt like our old system was random and kind of lucky if we caught everything."

Random is expensive. A close that runs the same way every month is how the missing 10% found its way back onto statements.

32 hours of bill pay down to one weekly run

Bill pay used to cost the operations manager her Mondays, every week, roughly 32 hours a month, and it was crowding out the operations work she was actually hired to do.

Today it's one weekly batch run. Vendors know when they get paid, payments go out together, and nothing needs a Square login or a checkbook. The hours came back to the role that needed them. The operations manager runs operations again.

Room to run the business again

The biggest result doesn't fit in a stat. The accounting burden had been quietly capping the company's growth. "It was impacting so much of the ability to actually scale and focus on the things that I love to do, which is hospitality," Sierra says.

That's what changed. With the financial operations running on a reliable system, Sierra's time goes to marketing, people retention, and growing the portfolio: the work that made Host My Home worth scaling in the first place.

Why Topkey

Sierra had already tried the generic tools, and they kept failing for the same reason: none of them understood that every dollar in this business belongs to a property. "The ability to assign per property is a very understated gain," she says. "It sounds really simple, but it's really kind of awesome to just be able to select it from the dropdown."

That's the difference between software built for expense reports and software built for vacation rental operations. When Sierra saw Topkey presented at VRMA, she recognized it immediately: "I need this, like, so bad. Like, I need this yesterday."

The experience since has matched the first impression. Whenever a question comes up, Sierra reaches out and gets a fast answer. "They've been very quick to respond," she says. "Anytime I've had a question, I've just reached out."

The Ceiling Wasn't the Team

Most vacation rental companies hit the same wall Host My Home did somewhere between 30 and 60 properties: the receipt chase, the payment sprawl, the week-long close. The team isn't the problem. The system is.

Sierra replaced hers, and the accounting nightmare became a close that runs the same way every month, five days faster, with the founder back focused on growth. If month-end owns your calendar the way it owned hers, see what Topkey can do for your operation.