Finance & Payment Operations Specialist

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TYPE OF WORK

Full Time

SALARY

2000

HOURS PER WEEK

40

DATE UPDATED

Sep 18, 2026

JOB OVERVIEW

This is a finance operations role, not a bookkeeping role.

We are a US direct-to-consumer telehealth company. We sell a subscription product, we spend on paid ads every day, and we run payments through more than one merchant account. Most of the numbers currently live in the founder's head and in a dozen separate dashboards. Your job is to get them into one weekly report that leadership can trust, and to see payment and cash risk coming before it becomes a problem.

You will sit between finance, subscription payments, paid acquisition, customer operations, and vendors. The work directly shapes how much the company spends on ads and how fast it grows.

WHAT YOU WILL OWN

Weekly reporting and reconciliation

Build and maintain the weekly executive KPI pack
Reconcile orders, rebill revenue, refunds, chargebacks, processor settlements, ad spend, and cash movement across source systems
Report revenue, contribution margin, CAC, approval rates, retention, and cash conversion in one place instead of five
Find discrepancies between systems and chase them down before the numbers go to leadership
Payment and merchant account operations

Maintain a weekly capacity map across processors: volume caps, reserves, approval rates, decline rates, chargeback thresholds, and routing rules
Monitor processor balances, settlements, rolling reserves, pending payouts, and any unusual change in payment performance
Support routing decisions and raise the flag early when an account approaches a cap or a risk threshold
Keep accurate records of processor fees, limits, reserves, and renewal dates
Cash forecasting and unit economics

Maintain a short-term cash and reserve forecast covering ad spend, settlement timing, reserves, fulfillment and clinical costs, refunds, and payroll
Track cohort economics and all-in profitability per customer, including CAC, fulfillment, clinician cost, processing, refunds, chargebacks, and commissions
Flag clearly when performance falls outside the agreed scaling limits
Help leadership tell the difference between revenue growth and profitable, cash-safe growth
Vendor and contract records

Maintain the contract register for material vendors: owner, status, commercial terms, renewal and termination dates
Collect and organize supporting documents for processors, pharmacies, clinician networks, and checkout platforms
Keep financial, payment, and contract materials current and easy to verify
Handle sensitive financial and vendor information with complete discretion

YOUR FIRST 30 DAYS

Get read-only access to the ad platforms, the checkout and subscription platform, the payment processors, and settlement reporting
Deliver the first repeatable weekly KPI pack, with sources and reconciliation notes written down
Deliver the first processor capacity map and reserve forecast
Document the payment routing and escalation procedure
Build the contract register for payment, clinical, pharmacy, and checkout vendors
If those five things exist and are reliable at day 30, this role is working.

WHAT WE NEED FROM YOU

Strong Excel or Google Sheets: complex formulas, pivots, data cleanup, and clean reporting. This is the core skill and we will test it
Real experience in finance ops, revenue ops, payment ops, or e-commerce operations
Experience reconciling data across multiple systems and finding the cause of a discrepancy, not just the size of it
Comfort with subscriptions and rebills, refunds, chargebacks, and settlement timing
The judgment to turn messy data into a short report with clear conclusions and honest open questions
Ability to work independently and remotely, and to be trusted with confidential financial information
Clear written English

HELPFUL TO HAVE

Multi-processor or high-risk payment environments, merchant accounts, rolling reserves, routing
DTC subscription, telehealth, pharmacy, or other compliance-sensitive operations
Stripe, CheckoutChamp, GoHighLevel, PostHog, Meta Ads, Google Ads or similar
Cash forecasts, cohort models, contribution margin reporting
Bookkeeping or accounting background, CPA studies, or controller support experience

WHAT WE PAY

Starts at $2,000 per month

THE SETUP

Full-time and remote. Most of the work is on your own schedule, with at least four hours of overlap with US Eastern business hours so you can raise payment issues while someone is awake.

HOW TO APPLY

1. Start your message with the word RECONCILE
2. Record a 3-5 minute loom video where you introduce yourself, walk us through your experience. Also, describe one time you found a discrepancy between two systems. What the two systems were, how you found it, and what was actually causing it.
3. Tell us about one spreadsheet or report you built that other people still use, and what it replaced
4. Shortlisted candidates get a short data exercise: a small anonymized set of orders, refunds, settlements, and ad spend, with a rolling reserve. We will ask you to produce a reconciled weekly summary, three things you would investigate, and one cash observation.

Please answer in your own words. Applications that skip the instructions above will not be read.

SKILL REQUIREMENT
Finance Management Revenue Management
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