Two things drive this. Claude can absorb about ten hours a week from the repeatable half of the job, and Asana added twelve buildings in July with no headcount behind it. Put those together and the same four functions rebalance: corporate accounting and entity compliance shrink, property support becomes the largest single piece.
Built around corporate accounting
Built around property support
Select a slice to see what that function covers.
| Function | Today | The role | What it covers |
|---|---|---|---|
| Property & portfolio support | 15% | 40% | Invoice coding and entry across the Asana book. Reporting support for DWS and South Loop. Budget preparation, vendor setup, and insurance certificate tracking. |
| Corporate accounting & AP | 40% | 25% | TDC budget and cash flow. Management and asset management fees, intercompany. Check runs and PayScan approvals. 1099s. The Miller Cooper year-end package. |
| HR & payroll | 20% | 20% | Paycor cycles and payroll allocations across properties. Fidelity 401k, Section 125, workers comp. Benefit renewals, onboarding, terminations. |
| Entity compliance & banking | 25% | 15% | The 155-entity filing calendar, reviewed monthly rather than assembled. BOI and CT Corporation. Wires, ACH, positive pay, bank reconciliations. |
The person we are describing is a small-company assistant controller or business manager, not a REIT senior accountant. Seven to fifteen years, multi-entity experience, comfortable in Yardi and a payroll platform, and genuinely good at reviewing work rather than only producing it. That last one is new, and it is the one to screen hardest for.
Written for the rebalanced version above.
Tucker Development is a Chicago-based owner, developer and manager of retail and mixed-use property. We are a small team, which means this role touches everything: corporate accounting, the entities, banking, payroll, and direct support to the people running our properties. You would work alongside our accounting and property management staff and report to the President.
We use AI tooling day to day, and this role does too. Much of the repeatable work here arrives already drafted: long documents summarised to the page that matters, filing deadlines tracked, reconciliations reduced to the exceptions. You approve, correct and decide. We are looking for someone who finds that a better job rather than a threat to it, and who will say plainly when the draft in front of them is wrong.
A CPA is not required and is not what this role needs. Our outside firm handles high-level accounting and tax.
The usual interview finds someone who produces accurate work. This role also needs someone who catches inaccurate work, and that does not show up on a resume.
Give them a one-page reconciliation with two planted errors and ask what they think. Whether they find both matters less than whether they push back at all. Some very good accountants will assume the sheet is right because we gave it to them.
Not how many properties. Entities. Someone who has managed forty legal entities across three states will say so immediately and have opinions about registered agents. Someone who has not will talk about departments.
Their answer tells you whether they see repeatable work as a burden or as job security. We want the first. It is also the fastest way to find out whether they have ever actually used these tools or only put them on a resume.
Separate from the hire, and easy to miss until it is urgent. Worth doing in September while there is time to fix whatever we find.
Nothing here waits on the hiring decision except the hire itself. The builds and the knowledge capture are worth doing whichever way the role is scoped.
The one hard constraint is the October start. A hire landing then gets a full quarter beside Joanne. Anything later and the handover becomes documentation instead of training.
These are things we already ask Claude to do, not a wish list. Worth being clear on the boundary: Yardi handles invoice capture, coding and indexing, and nothing here duplicates that. The pattern in all eight is the same. It reads, compares and summarises, and a person decides.
Someone reads a forty-page loan agreement, lease or service contract and takes notes, then re-reads it the next time a question comes up.
One page: term, rate, covenants with their test dates, reporting deadlines, and anything that triggers a default. It tells you where each figure came from, so checking it takes a minute rather than an afternoon.
Open each lease, certificate or statement in turn and type the same handful of fields into a spreadsheet. Forty documents is most of a day, and the fortieth gets less attention than the first.
One table with the same fields pulled from every document, and a flag on anything it could not find rather than a quietly blank cell. You check the flags instead of retyping the set.
Two drafts of a lease open side by side, or this month’s rent roll against last month’s, read line by line to find what moved.
What changed, what is new and what disappeared, with the clause or the line quoted. It catches the deletion nobody was looking for, which is usually the one that matters.
A deposit lands that does not obviously match an invoice. Someone works backwards through the aging, the ledger and the tenant’s history until it makes sense.
Hand it the deposit detail, the aging and the open charges. It proposes what the payment clears and says how sure it is, so the genuinely ambiguous ones surface first instead of last.
A bank statement against the ledger, or vendor payments against the W-9s on file, read line by line by eye.
Only the lines that do not match, with the difference on each. Roughly eighty percent of the work, and no credential ever leaves your hands.
Eight templates copied from blanks, each renamed by hand to the period and property code, filled, copied again into a delivery folder, zipped. Twelve times a year.
The set stamped and staged in minutes with consistent names, then checked before it goes out. Five versions of the same file with a typo in the date stops being possible.
A blank comment box on every line over threshold, and a deadline.
A first-pass explanation on every line, with the ones it is guessing at marked. You edit and replace rather than compose from nothing.
Everyone means to document their process. Nobody has a spare week, so it does not happen until somebody leaves.
Procedures written while the work is being done rather than as a separate project. This is the one already running, and it is why Joanne’s handover is further along than it would otherwise be.
Claude is good at the paperwork around the money and has no business moving it. It never holds a banking credential, so wires, ACH release, positive pay and payroll submission stay entirely with a person, and Yardi's MFA means every posting does too. The judgment calls stay human as well: whether an invoice is real, whether an entity is exempt, what next year's budget should assume. What changes is that people spend the day deciding rather than assembling.
Replacing her job as it stands is the lower-risk option and the easier posting to write. It also puts everything Claude gives back into corporate work, which is the part of the job that needed the least help, and leaves the property side exactly where it is.
The alternative is to scope the role deliberately: the same corporate core, with the hours Claude returns reserved from day one for invoice entry, DWS support and whatever Lindsey and Teresa need that week. It is the only version that adds capacity where the portfolio actually grew, without a second hire.
One decision sits underneath it either way. The 155-entity filing calendar is our largest penalty exposure and the piece with the least reason to stay in-house. Moving it to CT Corporation's managed service is worth pricing regardless of how we scope the hire.
Sources. Folder structure and ownership across Accounting, Legal & Financial and Admin; the 2026 entity filing log (155 entities); TDC Accounting Check Lists dated 01.01.2020; the Asana Portfolio workload assessment of 5/9/26; staff meeting notes of 5/12, 5/19 and 7/21/26; the Cowork rollout pack.
Estimates. The percentage split and the ten-hours-returned figure are my own and are directional. The 0.9 to 1.3 FTE Asana figure and the 2.25% fee model are Tucker's own numbers from the May documents. Nothing here has been validated with Joanne, Teresa or Lindsey.