How Premier Group Got Its Month-End Back and a Seat at the Table in Wildfire Mitigation
About Project
Premier Group runs luxury property management, construction, and roofing companies in Aspen, with one CFO keeping the books for all of them. Columnline cleared a six-month books backlog, took the typing off her desk, and built the wildfire platform that put Premier in front of FirstOnsite’s executive team and Aspen Skiing Company.
About Premier Group
Premier Group is a family of companies in Aspen and Snowmass: about 70 luxury homes under management, custom homes from $5 million to $40 million, and crews running excavation, landscaping, roofing, and development. It grew on referrals for 20 years, and the back office did not keep pace.
CFO Jill Whittaker kept the books, ran month-end billing, and entered the property schedule by hand, seven days a week. CEO Jesse Allen wanted to grow on technology, not headcount: “Instead of going like, oh, we need three more guys, it’s like, okay, we need two more guys and a little bit more tech.”
So the finance desk came first.
- Company
- Premier Group, Aspen and Snowmass, Colorado
- Industry
- Luxury property management, custom home construction, excavation and landscaping, roofing, and development
- Size and scale
- Six divisions. About 70 luxury homes under management, growing toward 100 to 125. Custom homes from $5M to $40M+.
- What Columnline runs
- Bank statement reconciliation, invoice drafting, and stay scheduling, plus the Premier OnSite wildfire risk platform Columnline built
- Tools it works with
- QuickBooks Online, QuickBooks Time, Nines, email, PDF bank statements
Before
- The bank feed dropped every two to three days
- Every transaction typed in by hand: about 6 hours per company, per month
- Past imports doubled or tripled entries
- Invoicing meant 14 to 16 hour days rewriting crew time entries
- Each guest stay took 10 to 15 minutes across three screens
- Six months behind, with taxes and a valuation on hold
After
- Statement PDFs are the source, so a dropped feed no longer matters
- Transactions arrive in QuickBooks; the CFO clicks match and approves
- Each transaction is checked against the books, and only missing ones load
- Draft invoices arrive merged, translated, and standardized
- The scheduling email becomes every entry, written in automatically
- Books caught up across all three companies
The Problem
Bank Reconciliation
Problem
The bank feed kept dropping, so the CFO became the bank feed
QuickBooks kept losing its connection to Premier’s bank, and each drop meant missing transactions. The only fix was typing them in from the PDF statement: more than 200 per company, with past bulk imports already causing duplicate entries.
The books fell six months behind. “It’s delaying our taxes and it’s delaying the business valuation,” Jill said at kickoff. A partner could not buy in until the books were right.
“It’s like six hours a month per company… I don’t have time for that.”
Jill WhittakerCFO, Premier GroupSolution
Statements in, clean books out
Columnline pulled 29 statements covering 13 months. The AI employee read every line, confirmed each statement’s transaction count and running balance, sorted transactions into Premier’s categories, and checked each one against QuickBooks so only missing entries loaded. Files were ready in four days, and once Jill confirmed the process, it rolled out to every company.
Bank Reconciliation agent
Turns bank statement PDFs into checked, categorized, duplicate-free QuickBooks entries for the CFO to match and approve.
“So now that they’re there… I just go match, match, match, match, match. … This saves me probably three hours of data entry.”
Jill WhittakerCFO, Premier GroupThe Problem
Invoicing
Problem
Month-end invoicing meant decoding crew notes
Property management sends about 60 invoices a month, and one landscaping invoice can run past 200 lines. Half the entries are in Spanish, many just one word, with six people on a job logging the same task. “Sometimes I have to really focus and try to figure out what they’re even saying,” Jill said. Rewriting them meant 14 to 16 hour days every month-end.
Solution
Invoices that start as clean drafts
The AI employee pulls field time from QuickBooks Time, merges duplicates, translates the Spanish, standardizes the wording, and builds a draft invoice in QuickBooks. Jill decides what is billable and sends it. The judgment stays with her. The rewriting does not.
Invoice Drafting agent
Turns messy crew time entries into consolidated draft invoices for the CFO to review and send.
The Problem
Stay Scheduling
Problem
Every guest stay meant 10 to 15 minutes of clicking
Stay dates arrive by email. Each stay needs an occupancy entry, inspections, and cleans: three to six entries across three screens. “Just that alone, that is a 10 to 15 minute process,” Jill said. With 70 homes, a missed departure clean was one busy afternoon away.
Solution
The email is the schedule
The AI employee reads the email the way a person would, sorting out mixed date formats, same-day turnovers, and mid-stay requests. It expands each stay into every entry, a person checks the list, and it writes them straight into Nines. The production run wrote 30 entries in 10 to 15 minutes, and about 98% of entries now land without a fix.
Stay Scheduler
Turns a scheduling email into the occupancy entry, inspections, and cleans, written straight into the property system.
The Problem
Wildfire Mitigation
Problem
A wildfire business has to earn the meeting
Premier launched Premier OnSite to plan and carry out wildfire mitigation around Aspen and beyond. The buyers who matter most, national restoration companies, ski resorts, insurers, and counties, have seen plenty of slide decks. A serious meeting takes something they cannot get anywhere else.
Solution
The customer’s own risk, live on screen
Columnline built Premier OnSite: 2.5 million parcels pre-assessed, live fire data, drought, wind and smoke layers, county hazard maps, an At Risk Today list, and 3D terrain. Premier walks into a meeting and puts the customer’s own property on the screen.
In May, Premier presented it to FirstOnsite’s CEO and executive team, the same day the two companies signed their memorandum of understanding. In July, Aspen Skiing Company’s mountain planning lead watched it run across his four mountains and asked for a second meeting with his mountain managers and emergency responders.
Premier OnSite
Scores wildfire risk parcel by parcel and turns it into a plan a homeowner, resort, or insurer can act on.
“I think this is an amazing tool that we really need to harness... The opportunities are endless.”
Jesse AllenCEO, Premier GroupResults
A six-month books backlog, cleared.
- A six-month backlog cleared for all three companies: 2,193 transactions from 29 bank statements, read and balance-checked within four days of kickoff.
- 18 hours a month of bank re-typing turned into a match-and-approve review.
- Invoices now start as drafts: crew time merged, translated from Spanish, and cleaned up before the CFO opens them.
- 30 schedule entries in 10 to 15 minutes, replacing up to 150 minutes of manual clicking.
- The wildfire platform on screen for FirstOnsite’s executive team and Aspen Skiing Company.
Outcome
The outcome
The biggest result was a six-month backlog, cleared, so the tax filing and the partner valuation could move again. About 18 hours a month of re-typing became a review, and the CFO felt it the moment the first company went live: about three hours of data entry, gone. “Thank you so much for saving me time,” Jill said.
The CFO’s month now starts with review: bank entries to match, invoice drafts to approve, schedules already written. Outside the back office, the same partnership gave Premier a wildfire platform that earned executive time at FirstOnsite and Aspen Skiing Company.
Next steps
What’s next
Columnline is building Premier Estate Management to replace Nines, with a homeowner portal, a standard inspection form, and work linked straight to QuickBooks invoices. A new website with a steady blog and Instagram calendar comes next, built to bring in more property management and roofing clients.
Want your finance team doing review instead of data entry? Book a call, and we will run this job at your company.