Full-Time Bookkeeper

Senior Bookkeeper
Company: Speak Your Way To Cash® (and affiliated entities)
Reports to: [Director of Operations]
Type: Contractor
Compensation: $800
Start date: ASAP

Have you managed books for a company doing $10 Million USD or more? Have you reconciled hundreds or thousands of transactions a month? Are you savvy with financial reports? Do you know how manage a large chart of accounts?

ABOUT US

Speak Your Way To Cash® is a three-time Inc. 5000 sales training company. We teach credentialed experts, licensed professionals, and service-based business owners how to land corporate contracts and sell from the stage. The team is 17 people and fully remote. The business runs on a launch model with one to two launches per month, plus live events, masterminds, and international retreats, so transaction volume is uneven by design — quiet weeks followed by heavy ones.

There are several related entities under the same ownership, including a law firm and a holding company. Books are kept separate and clean across all of them.

THE ROLE

We need a senior bookkeeper who owns the numbers day to day. That means reconciling transactions daily, closing out and reporting weekly, and running a full month-end close that leaves nothing for our CPA to untangle at tax time.

This is a maintenance and accuracy role, not a strategy role. The person who does well here is the one who notices that a deposit doesn't match, chases it down the same day, and tells us before we ask.

WHAT YOU'LL DO

DAILY

• Reconcile all bank, credit card, and payment processor transactions daily
• Code expenses correctly to the right entity, class, and category
• Flag anything that looks off — duplicate charges, missing receipts, unusual vendor activity, deposits that don't tie to a known launch or invoice

WEEKLY

• Follow-up on any unpaid invoices or failed payments across stripe, paypal, and fanbasis
• Deliver a written financial report covering cash position, revenue by offer, outstanding AP and AR, and any open items you need answered
• Reconcile revenue across payment processors and our sales platform so what the platform reports matches what actually hit the bank
• Track contractor payments and outstanding invoices

MONTHLY

• Run a full close: reconciliations complete, accruals recorded, journal entries posted, books locked
• Produce P&L, balance sheet, and cash flow statements with a short written summary of what changed and why
• Reconcile event and travel spend against budget

ONGOING

• Maintain clean, current books across multiple entities without commingling
• Manage 1099 tracking and year-end contractor reporting
• Prepare and hand off documentation for our CPA at tax time
• Keep receipt and documentation systems organized enough that any transaction can be traced in under five minutes

AI PROFICIENCY REQUIRED

AI proficiency is required. Candidates must be able to use AI tools effectively in their day-to-day work, verify outputs for accuracy, protect confidential company and client information, and explain a practical example of using AI to improve work quality or efficiency.

WHAT YOU NEED

• Five or more years of bookkeeping experience, including at least two years at the senior level
• Experience working inside a firm — an accounting or CPA firm, or a law firm. You should know what it looks like when books are held to a professional standard and reviewed by someone else.
• Advanced QuickBooks skills. You should be comfortable with bank rules, class and location tracking, journal entries, undeposited funds, and cleaning up someone else's mess in QuickBooks without starting over.
• Experience managing books for more than one entity at a time
• Experience reconciling high-volume transactions from payment processors, not just a single business checking account
• Full ownership of month-end close in a prior role, start to finish
• Strong written communication. Much of this job is telling us what you found in writing, clearly, without being asked twice.
• Ability to work independently on a remote team and hit recurring deadlines without reminders

NICE TO HAVE

• Law firm trust accounting or IOLTA experience
• QuickBooks ProAdvisor certification
• Experience with online course, coaching, or event-based businesses where revenue comes in launches
• Familiarity with Stripe, GoHighLevel, Dubsado, or Gusto
• Experience supporting a business through fast revenue growth

WHO THIS IS NOT FOR

• Anyone who needs daily direction to know what to work on
• Anyone whose experience is limited to one small business with low transaction volume
• Anyone who has never closed a month or handed off books to a CPA
• Anyone who would rather do tax strategy than reconcile accounts

HOW TO APPLY

Email ---------- and copy ---------- with the subject line SENIOR BOOKKEEPER.

Include:

• A loom video detailing your bookkeeping experiece
• Your resume
• A short note (under 300 words) describing the most disorganized set of books you have taken over and what you did to clean them up
• The number of entities you currently manage books for, and the approximate monthly transaction volume across them
• Your QuickBooks certifications, if any

Finalists will complete a paid reconciliation exercise using sample data before any offer is made.

Applications without the subject line will not be reviewed.