Contract Bookkeeper Jobs in Spring Hill, FL (NOW HIRING)

Help Us Change the Way People Use Technology
At DGR Systems, we're about connecting companies to the right solutions and enabling them to gain the most value from their investments. We go to great lengths to hire great people because, at our core, our clients deserve to have each person working on their project bring qualified expertise, a can-do attitude, and experience-based strategic insights to the table. They need to trust their IT consulting firm as a partner who is there to help accelerate their success and not pass them off to a junior team after the contract has been signed. Want to join us?
THE ROLE
DGR Systems designs, builds, and delivers technology for organizations that depend on it working. Behind every project sits a chain of purchase orders, distributor invoices, drop-shipped deliveries, client billing, and vendor programs that settle months after the work is done and every link of it has to land in the record correctly and on time.
That is this job. Not data entry, ownership. You will run the transactional accounting that everything else in the business is built on, and you will own it end to end rather than executing pieces of it for someone else.
You will report to our Director of Finance, Risk & Compliance and work closely with a Staff Accountant. The finance team is growing, and this seat is central to how it is being built.
WHY THIS ISN'T A STANDARD BOOKKEEPING JOB
If your experience is at a company that receives everything to its own dock and bills a flat rate, this will be a step up, and we would rather say so plainly than have you discover it in month two.
A single client engagement here can involve a purchase order to a distributor, goods shipped directly to the client site, a partial delivery with the balance on backorder, a vendor credit issued weeks later, freight billed separately, sales tax across state lines, and services invoiced against milestones. Matching all of that correctly takes more than accuracy.
It takes knowing what should be there and noticing when it isn't. That is the skill we hire for, and it is the reason this role sits above a standard bookkeeping seat.
WHAT YOU'LL OWN
This role covers both sides of the transaction cycle today. As the finance team grows, these seats specialize, which is the point at which your depth on one side becomes the reason you own it.
Purchasing & Payables

• Purchase order entry and maintenance, including partial shipments and backorders against a single order

• Three-way match across purchase order, vendor invoice, and receipt; including drop-shipped goods that never reach a DGR facility

• Distributor statement reconciliation and dispute resolution

• Vendor credits, return authorizations, price protection, and restocking adjustments

• Freight capture and allocation

• Vendor records and payment run preparation

Billing & Receivables

• Client invoicing against purchase orders, including milestone and progress billing on services

• Deal-specific pricing applied correctly rather than defaulting to list

• Sales tax applied by shipment destination and registered jurisdiction

• Cash application against remittance advice, including short-pays, deductions, and unapplied cash

• Receivables aging and collections correspondence

• Deferred revenue scheduling on subscription and maintenance renewals

You will also keep the desk documentation for your work current and improve it where it is wrong. We treat that as part of the job, not as something to get to later.
HOW WE WORK

• We work to a cycle, not a deadline. The record stays current rather than being reconstructed before close.

• The rules will be written. When to hold a document and ask, and when to post it and flag it, will be decided and written down. We don't want anyone to work by 'best guess'.

• Exceptions are the job. The routine transactions are what make room for the exceptions. Finding the one invoice out of two hundred that is wrong is the highest-value thing you will do in a given week.

• Traceable work. Every entry should tie to evidence someone else can follow without asking you. That is the standard that protects our business.

WHAT WE'RE LOOKING FOR
You'll Need

• Full-cycle accounts payable or accounts receivable ownership in a business that moves physical goods against purchase orders

• Three-way match experience - purchase order, invoice, and receipt - including what to do when they disagree

• The discipline to work to a cycle and stay current rather than batching

• A concrete example of a discrepancy you found, what made you look, and what you did about it

• The habit of leaving work someone else can pick up and follow without a conversation

It Will Help If You Have

• Worked in distribution, wholesale, resale, or contracting; anywhere drop-ship, partial shipment, and vendor credits are routine

• Reconciled distributor or supplier statements and worked their portals

• Handled sales tax across multiple states

• Touched deferred revenue or subscription billing

• Been through an accounting system conversion

We'll Teach You

• Our systems, tooling, and chart of accounts

• How OEM and partner programs work

• The IT product and services landscape, if you are coming from another industry

WHO THIS ISN'T FOR
We would rather be direct than waste your time.

• If exceptions feel like what gets in the way of the real work, the job is backwards from how we see it.

• If you would rather post something and move on than stop and ask, this will be a difficult fit. Asking is not a delay here; it is the expected behavior.

• If a reconciliation that will not tie is something to force closed rather than something to chase, we are not a match. There is no deadline that justifies that here.

• If you want a role where the work is the same every day and no one asks you to improve it, this role will ask.

COMPENSATION & BENEFITS
Base salary range $58,000 - $72,000
Work arrangement - Hybrid - Office Anchored
DGR Systems also offers a robust company benefits package designed to support employees and their families, including competitive health and welfare benefits, paid time off, retirement savings support, and other company-sponsored programs.
HOW TO APPLY FOR THIS ROLE
Send a resume and a short note about a discrepancy you found that nobody asked you to look for. Include what made you look, and what happened next. It does not have to be dramatic. We are more interested in what made you notice.
Apply to: joinus@dgrsystems.com
DGR Systems is an equal opportunity employer. We consider all qualified applicants without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other protected characteristic.
We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.
The pay range for this role is:
58,000 - 72,000 USD per year (DGR Systems)