How First Chair Saves Nearly 475 Hours a Month with Topkey

First Chair manages 4,400+ ski, coastal and lake homes across Colorado, Idaho, Montana, California and New England, with more than 400 employees. It runs Streamline as its PMS and Sage for accounting, with Breezeway in the field and Ramp cards in employees' hands.

Tim Koropsak, CFO, and Alan Marandola, Controller, led the finance build. Travis Finnan, Senior Manager, Accounting and Finance Systems, joined a month before go-live and runs Topkey day to day. The team automates before it adds people, and it needed software that could handle the volume and a partner that could keep up.

The Challenge: Enterprise Volume at Every Step

First Chair came to Topkey already operating at scale, with thousands of homes, more than 400 employees and four core systems, so card charges, tasks and bills arrived at enterprise volume.

Card Spend without a Short-Term Rental Layer

First Chair's operations team makes most of its purchases on Ramp cards, close to 10,000 transactions since launch. Ramp isn't built for short-term rentals. "Ramp didn't have our units in there," Travis says, and it had no way to tie a charge to the Breezeway work order behind it.

On its own, that would have meant workarounds. Each charge would have to be matched to a unit and a job by hand, then keyed into Streamline and Sage. First Chair launched on Topkey, so the team never had to work that way, but Travis estimates that kind of manual work would take close to 10 extra people.

Approvals across 400+ Employees

Every one of those charges also needs someone to approve it. First Chair has more than 400 employees across its markets, with people joining and leaving across those roles. Every new hire needs a card, a place in the field system and an approver, and every departure leaves charges and reimbursements that still need sign-off. When someone left, any transaction waiting on them could stall.

The rule itself is simple. Every charge is signed off by the person above whoever made it. Keeping that true across hundreds of people, cards and reimbursements, while people come and go, is where it gets hard.

Volume Too High to Review by Hand

By Travis's count, Topkey has taken in close to 100,000 Breezeway tasks, about 10,000 card transactions and about 50,000 bill lines since launch. Cleaning alone produces thousands of task lines every week, and every task that carries a cost has to be tied to a property, coded and sorted into what the owner pays and what First Chair covers.

Most of that coding repeats. "If we're doing hot tub maintenance, it's always going to be hot tub maintenance," Travis says, and 99% of the time it's coded the same way. Without a way to apply that automatically, every item would wait for someone to review, code and push it through, even after a GM had already approved it in Breezeway. One blanket rule wouldn't work either. "On the East Coast, it's owner billable. In the West, it wasn't owner billable," he says of trash pickup, so a single rule for every market would only create cleanup work for another team.

Travis has seen where that leads. In prior roles, he watched teams assigned just to review thousands of owner statements, and when software couldn't do something, the fix was a new hire. "We have to hire someone to click buttons, right? And it's like, it's not really the best solution," he says. Tim wanted the opposite, a system that could separate charges billable to owners or HOAs, pull in Breezeway work orders and break invoices into line items without anyone splitting them by hand.

Field Work Spread across Disconnected Systems

First Chair's field teams cover five regions, and what they do shows up in different places. Cleans, repairs and guest calls become Breezeway tasks, purchases land on Ramp cards, vendor invoices arrive on their own, and owner charges have to end up in Streamline. Without something tying those pieces together, finance would have no single place to see what was done, what it cost and who approved it.

First Chair didn't want to solve that by pushing accounting onto the field team. "Their job is to be in the field to get a task done," Travis says. The person doing the task often isn't the one deciding how it's billed, and GMs already review every card charge and Breezeway task in their markets.

Finance also needed a record that holds every task. When a unit switched to non-renting in Streamline, its tasks, and the staff pay data tied to them, dropped out of Breezeway's reporting. At 4,400+ homes, that data can't disappear when a unit's status changes.

Scattered Costs and Missing Receipts

Even one job's costs can land months apart. A single repair can mean a card charge for parts, the technician's labor and a vendor invoice, three costs that each arrive at a different time. "Owners don't want to have a credit card charge and a labor charge and an invoice in three different months, and they'll have different names on them," Travis explains. First Chair manages these homes on the owners' behalf, so every charge has to be explainable.

The receipt matters too, because it's the owner's backup for their taxes. "I've lived in a world where 90% of the time those receipts are missing by the time it gets to the end of the month," Travis says. Some field teams work inside one or two buildings, while others drive 200 miles a day to reach five or six homes, often with spotty cell service, so snapping a receipt isn't always easy.

Owner Charges That Have to Hold Up

Only owner-billable charges go into Streamline, where First Chair builds owner statements, so each one has to land on the right owner, unit and month. Mistakes are expensive to undo there. Fixing one pushed line in Streamline takes seven or eight clicks, and "I've done a hundred transactions wrong, and it took me seven hours to fix that," Travis says. First Chair needed to manage those charges from a system where corrections are quick.

Getting the charge right is only half of it. Owners also want to see where their money goes. At a small company, the person answering an owner knows them on a first-name basis, along with the home and its history. "When you start to scale a big company, you kind of lose that level of it," Travis says, so at 4,400+ homes the answers have to come from the data.

Waiting for month-end doesn't help either. Owners don't want a statement that says "surprise, you made this much money," Travis says, or "three pages of stuff to go through." In his past roles, finding an answer meant pulling a report from one tool, then going into another system to find the invoice behind it, and month-end often ran on estimates. First Chair wanted owners to get real numbers, with the detail behind every charge.

A Partner Who Knows Short-Term Rental Finance

First Chair runs Streamline, Breezeway, Ramp and Sage together, a combination few operators share, so a lot of customization goes into making them work as one. Every change touches more than one system, and a fix in one place can ripple upstream or down.

Most software partners aren't set up for that. "You're used to working with these older, established software systems, and it's like, oh, we can't really change things," Travis says. In past implementations, support meant a queue or an offshore contact, and feature requests could sit on a roadmap for quarters. First Chair needed one partner that would work across the whole stack with them.

AI raised the stakes. Travis could see what it might do for a team like his, but building it in-house wasn't realistic while the team was busy getting a new stack live. First Chair needed a partner that understood both AI and short-term rental finance.

The Solution: Connected Tools and a Partner That Builds

First Chair came to Topkey with thousands of homes and built its processes as it grew, so it needed more than software. Topkey became the partner guiding that build, connecting Breezeway, Ramp, bill pay, Streamline and Sage into one flow and shaping each workflow around how First Chair actually operates. When the team needs something new, Topkey builds it with them.

Ramp Cards Connected to Topkey

Ramp gives First Chair's team cards and rewards they like, but on its own it doesn't know which home a purchase was for or who should pay for it. Topkey's Ramp integration adds that piece. First Chair's Ramp cards connect directly to Topkey, and every charge flows in automatically, already matched to the cardholder who made it.

From there, each charge is coded to a unit, so it's clear which home it belongs to and whether the owner or First Chair pays, and it routes to the right manager for approval. "We want our transaction data to be in Topkey because that's where everything else is," Travis says, since the units, receipts and work orders already live there.

Once a charge is approved, Topkey sends the owner's share to Streamline and the expense to Sage, so no one keys card spend into either system by hand. Close to 10,000 card transactions have come through that way, without the offshore data-entry team Travis expected that volume to need.

Adding new cardholders is just as light. When a new Ramp card is issued, Topkey matches it to the right user automatically, so "there isn't really anything we're doing," Travis says, beyond placing each person in an approval group. From then on, that cardholder's charges flow to the right approver without manual setup.

Rules and Approvals That Scale

Topkey lets the team set a coding rule once and apply it automatically. A rule can say that a certain type of task, bill line or card charge always gets the same GL code, unit or bill-to, and Topkey applies it the moment the item comes in.

"If we weren't able to set up rules with Topkey, you'd have to have someone reviewing them," Travis says. Instead, once a GM approves a task, it codes and moves through on its own, without an accountant pushing it by hand.

Approval workflows decide who signs off on each charge before it's paid or billed to an owner. First Chair built them around its own org chart. Each employee sits in an approval group, GMs approve the card charges in their markets, and every group includes the people above, so nothing stalls when someone leaves. Travis, Alan and Tim sit on every workflow as a final backstop.

Onboarding is quick, too. A bulk onboarding tool copies a peer's groups, approvers and role to a new hire in one step, so a new GM or housekeeper is ready without anyone rebuilding their setup by hand. When Travis needed to see which employees had banking details in place before issuing reimbursements, Topkey built the report right away, and he added his own filter to it in "30 seconds" so payments only go to people who are set up.

Breezeway Integration Turns Tasks into Work Orders

Topkey became the one place for First Chair's field work and its costs. Through Topkey's Breezeway integration, each Breezeway task comes into Topkey as a work order with its completion, approval and cost. The field team spends its day on cleans and repairs without leaving Breezeway, while finance works close to 100,000 tasks from one screen, with each cost next to the work and nothing rekeyed.

One click on the task ID in Topkey opens that task in Breezeway, so Travis can get context without searching. First Chair now starts task names with a number tied to a template, such as 01 for hot tub internal labor and 90 for trash removal by an outside vendor. When a work order lands in Topkey, Travis can tell from the first two digits what kind of work it was and how it should be coded.

Topkey also keeps every task it has taken in. When the non-renting units dropped out of Breezeway's reporting, "Topkey has retained that information through the API," Travis says. It also imports each Breezeway employee ID onto assignees and work orders, so finance has a complete record of the work behind staff pay and owner charges.

Work Orders Tie Every Cost to the Job

The work order is where the costs come together. A tech paints a unit and picks up supplies at Home Depot, and the card charge attaches to that job's Breezeway work order. It waits there for approval from the right manager before it's billed back to the owner, and vendor invoices link to the same Breezeway task ID.

The card charge, the labor and the invoice all point to one job instead of three unrelated lines, so nothing is billed to an owner without its job and approval behind it. For Tim, that's the point. Topkey pulls in Breezeway work orders and centralizes cost management in one system. When an owner asks about a charge, the work order shows what was done, what it cost and who approved it, so the team can answer without digging through three systems.

Bill Pay Codes Every Line on Arrival

Topkey's bill pay tool is where First Chair's vendor invoices come in, get coded and get paid. As invoices come in, Topkey's AI reads each one, matches it to the vendor and breaks it into individual line items. It then finds the unit for each line from the address on the invoice and codes it, so most of the work is done before anyone opens the bill.

That matters at First Chair's volume. A supply invoice can run 104 lines, each of which would otherwise need a property chosen by hand. "They're sending 55 lines… and we're just ingesting it and it's coding it right then and there," Travis says of a hot tub service bill. Tim sees the same payoff on the AP side, where no one has to split invoices into line items manually.

Paying vendors stays in the same place. Through vendor management, vendors enter their own payment details, so finance never sees their banking information, and approved bills are paid from Topkey. About 50,000 bill lines have come through this way, handled by First Chair's small AP team.

Streamline Integration Pushes Owner Charges

Streamline is where First Chair builds its owner statements, so every charge an owner pays for has to end up there. Topkey's Streamline integration sends those charges over automatically, whether they started as a Breezeway work order, a card charge or a vendor bill. Travis chose what each one carries, including the memo, the vendor and whether the receipt goes with it, and Topkey fills in each unit's location, a required field in Streamline.

Because the integration follows First Chair's own Streamline setup, a charge can only go where Streamline expects it. "There's really no room for error in that," Travis says. And because the push runs off each work order's status, owner charges reach Streamline in real time, as soon as the work is closed.

Corrections happen in Topkey, too. Where fixing a line in Streamline takes seven or eight clicks, in Topkey Travis can "just revert it and redo it." Once a charge is closed, "I'm doing everything in Topkey," he says, so no one rekeys owner charges into Streamline, and statements are built from charges that already carry their job, receipt and approval.

Owner Questions Answered from One Place

Owner questions can land with anyone, and most of First Chair's leadership team is remote. In Topkey, every transaction sits with its receipt, its unit and the work order behind it, so anyone on the team can look up a charge and see what was done, what it cost and who approved it without asking around. Owners can get that detail too, since each charge on an owner's statement traces back to its job and receipt in Topkey.

A Hands-On Strategic Partnership

Beyond connecting Breezeway, Ramp, Streamline and Sage, Topkey's team works alongside First Chair's finance leaders, joining working sessions, mapping out workflows and bringing expertise the company doesn't have in-house. "You guys have extreme knowledge when it comes to AI that I don't have," Travis says, and it shows in the AI that reads and codes every bill line.

When First Chair needs something new, Topkey builds it with them instead of putting it on someone else's roadmap. Since launch, that's 158 feature updates, including rules that let repeat Breezeway tasks code themselves, an automatic push to Streamline when a task closes and a bulk onboarding tool for new hires. Alan calls Topkey's ability "to enact and put into production tens and hundreds of various requests" unmatched.

Often, the fix arrives before First Chair has to ask twice. "A lot of times you guys have come up with something and it's already done before I even realize it," Travis says. When Topkey set each unit's location to fill in automatically, it "was fixed within 48 hours." "It's insane, the manpower that you guys have eliminated," he says. Early on, a Topkey engineer also re-ran 4,000 card line items through First Chair's workflows in one pass, work Travis would otherwise have redone one transaction at a time and says he didn't know how he'd have managed on his own.

That's what the partnership looks like day to day. New ideas keep coming from Travis, Alan, Tim and Topkey's engineers, and the two teams work through them together, so First Chair's setup keeps getting more efficient as the company grows.

The Results: Automation in Place of Headcount

By automating the repeat work, Topkey turned First Chair's enterprise volume into something a lean team can run. Work orders, card charges and bills now code and move through on their own, giving the team nearly 475 hours a month back.

Roughly 100 Hours a Week of Manual Financial Work, Automated

Topkey automates the everyday financial work behind First Chair's 4,400+ homes. Card charges and Breezeway tasks are coded as they come in, invoice lines are matched to the right unit, and owner charges flow to Streamline without anyone rekeying them. Travis estimates that saves the team roughly 100 hours a week.

Owner statements show how that happened. Early on, Travis was coding every owner statement line himself, one bill or card charge at a time, and planning to push through overnight. "I couldn't have done it by myself," he says. "It would have been a full-time hire." When Topkey's team saw what he was doing, they built bulk actions so he could code 100 lines at once.

"Topkey is obviously our biggest partner in automating things," Travis says. With rules, bulk actions and Breezeway work orders handling the repeat work, no one has to touch the same line twice.

Nearly 75 Hours a Month Back from Cleaning Bills

Every clean at First Chair is a Breezeway task, and every task carries a cost owed to the cleaner who did it. With thousands of cleans a week, that added up to 4,000 to 5,000 cleaning lines to approve, code and pay, every week.

Each of those lines had to move through four steps, from approved work order to bill, through coding and into ready to pay. A single run took easily 24 hours, and two team members were dedicated to pulling work orders through.

The fix started with a vendor. One had been sending a separate bill for every stay, so First Chair asked, in Travis's words, "Stop giving us 100 pieces of paper. Can you send us a statement at end of the month?" Travis wondered whether cleaning could work the same way. He brought the idea to Topkey, and Topkey built it. Each cleaning vendor's tasks now roll into one bill, and every cleaning vendor is paid from one place.

Three of the four steps are gone, and bill pay is no longer clogged "with tens of thousands of lines." That's about 18 hours a week, nearly 75 hours a month, back for the team, and the same one-bill-per-vendor approach can work for any vendor that bills by the task.

A Field Team Focused on the Field

The impact reaches the field, too. First Chair's operations team works entirely in Breezeway. Housekeepers, maintenance techs and GMs log their work there, and Topkey picks up the costs behind it, so no one in the field has to learn a second system or chase accounting steps after a job.

For Travis, that's one of the biggest payoffs for the business, because it frees the ops team to focus on operations. Time that would go to coding and paperwork goes back to the turnovers, repairs and guest requests that keep 4,400+ homes running.

Owner Billables That Don't Slip Through

Every dollar First Chair spends on an owner's home has to make it onto that owner's statement, or the company absorbs the cost. With card charges, labor and vendor invoices tied to the same Breezeway work order, owner-billable costs stay attached to the job they belong to instead of getting lost between systems.

Each one is approved and then flows to Streamline, landing on the right owner's statement with the receipt and job behind it in Topkey. "I think the pass-through is perfect," Travis says of what Topkey sends to Streamline. That closes the gaps where cash leakage usually starts.

Owner Answers within 24 Hours

In short-term rentals, owners expect answers quickly. "I have the ability to answer a question as if I were there, because now I have all the information at my fingertips," Travis says. With Topkey as the source of truth on the expense side, he can get an owner a response within 24 hours.

Travis also sees the numbers sooner. "I'm not waiting until month-end to have unit-level financials," he says, and he's looking at them by business day five, six or seven. When an owner asks a question mid-month, the team can often sort it out while the stay is still happening.

Tim sees the same thing at the leadership level. "Topkey allows us to see where we are failing, and take proactive steps to fix those areas," he says. "Having disparate systems would make that process nearly impossible." For Tim, that visibility is central to protecting margins.

Enterprise Output from a Lean Team

Together, that automation is how a finance and AP group of five or six handles the financial work behind 4,400+ homes and more than 400 employees. It automates the repeat financial tasks and connects Breezeway, Ramp, Streamline and Sage, so data moves between tools without anyone reverifying or rekeying it. Done by hand, Travis estimates that would take close to 10 more people.

"You guys are very quick to help automate, versus us needing to throw a person at the problem," Travis says. Each new piece of automation is work the team never has to hire for.

Approvals spread the work across the company instead of piling it up in finance. Responsibility sits with the GMs and managers closest to the work, while finance keeps the checks and balances that make sure every charge is right before it's paid or billed to an owner.

New hires are set up in one step, nothing stalls when someone leaves, and the finance team spends its time reviewing and approving instead of moving data between systems.

Why Topkey: A Partner That Builds alongside Them

What sets Topkey apart for First Chair is how its team builds alongside them, and all three of First Chair's finance leaders describe it the same way. "This is honestly the most responsive and collaborative partner I've ever worked with," Tim says. Travis calls it "unlike any partnership I've ever had with another entity," and Alan calls it "a level of service that is second to none." All three came to that view on their own.

That starts with access. "You guys pick up the phone, you answer emails," Travis says, and he can get Topkey on a call within an hour, while Alan gets a meeting within 24 hours. For a company rolling out a new stack across 4,400+ homes, that means problems don't sit and wait. During rollout, Topkey even took on First Chair's help desk tickets from users and vendors, so those questions didn't pile up on the finance team during setup.

Travis does much of First Chair's Topkey work himself, but he's never stuck. He's met nearly everyone at Topkey, from his day-to-day contacts to the engineers who build the product, and when a question needs an expert, Topkey brings that person onto the call. Alan says that from onboarding on, Topkey "was clearly dedicated to our success and how they can be an extension of our company." With Topkey behind them, First Chair's team is free to rethink how it operates, knowing Topkey will help build it, instead of falling back on the old answer of hiring more people just to keep up.

Built for Enterprise Operators Who Want Strong Finances

Every enterprise vacation rental operator runs a little differently. Each has its own mix of systems, its own rules for what owners pay and processes that keep changing as the portfolio grows. A standard setup only gets them so far. They need a partner that builds around how they operate and helps guide what comes next.

That's what First Chair found in Topkey. Topkey connected Breezeway, Ramp, Streamline and Sage around First Chair's own workflows, shipped 158 feature updates alongside its team and brought short-term rental finance and AI expertise the company didn't have in-house. A lean finance team now runs the financial work behind 4,400+ homes, with a partner that keeps building as First Chair grows.

If your operation needs more than software, see how Topkey can partner with your team. Book a demo.