Billing Supervisor

Entech Computer Services LLC • Fort Myers, FL

17h

About The Position

The Revenue Assurance Manager (Billing Supervisor) is responsible for ensuring that all signed client agreements are accurately converted into operational and financial records within the company systems. This role begins when an opportunity is won and a proposal is signed. The primary objective is to ensure agreements are properly structured in the PSA, vendor costs are validated, invoices are created accurately, and billing is set up for long-term success. This position plays a critical role in protecting revenue integrity by ensuring that what is sold is correctly implemented in the financial and operational systems before services are delivered or billed.

Requirements

• 2-5+ years of experience in: Billing, revenue operations, accounting, or finance. Revenue recognition and/or recurring revenue environments
• Experience working with PSA systems (e.g., ConnectWise, Autotask, Halo) strongly preferred
• Background in managed services (MSP), SaaS, or subscription-based business models preferred
• Experience translating sales agreements or contracts into billing and financial systems
• Proven ability to manage: Contract setup and validation, Invoice creation and billing schedules, Vendor cost reconciliation and margin validation
• Valid Florida Driver’s License required.
• Passing of a level 2 background check
• Passing a pre-employment drug screening

Nice To Haves

• Bachelor’s degree in Accounting, Finance, Business Administration, or related field preferred. Equivalent work experience in lieu of a degree may be considered.
• Certified Management Accountant (CMA) preferred
• Certified Public Accountant (CPA) preferred
• Certified Revenue Management Professional (CRMP) preferred

Responsibilities

• Lead and oversee the revenue assurance and billing setup function, ensuring signed client agreements are accurately converted into operational and financial system records.
• Supervise and review the work of billing and revenue operations staff, providing direction, quality control, and escalation support as needed.
• Ensure accurate billing activation for new and amended agreements, including pricing, quantities, billing cycles, start dates, renewals, and invoicing schedules.
• Validate vendor costs, margins, and COGS tied to client agreements to protect profitability and identify discrepancies prior to billing.
• Oversee the creation and approval of initial and recurring invoices, including down payments, implementation fees, and first-month billing.
• Serve as the primary operational liaison between Sales, Finance, and Delivery, ensuring clear handoff of contract terms, billing requirements, and service structures.
• Audit agreement and billing setups for accuracy and compliance, resolving issues proactively before services go live or revenue is recognized.
• Develop and improve revenue assurance processes and controls to strengthen billing accuracy, consistency, and system integrity.
• Maintain documentation and reporting to support revenue accuracy, compliance, and internal audits, while upholding HIPAA and information security standards.

Benefits

• Free Employee Medical Insurance
• Additional Employer Paid Medical Options
• Fully Vested 401(k) Match
• Flexible Time Off (an unlimited amount of paid time off days)
• Free $10,000 Life Insurance Policy
• Six Paid Holidays – PLUS Black Friday!
• Flexible Schedule Options
• Fun Employee Events – Yearly Culture Building Events
• Options available for dental, vision, accident, hospital, short term disability, long term disability, Identity theft protection and additional life insurance.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Number of Employees: 11-50 employees