Billing Support Specialist

LeadStack Inc.; United States; Remote; USD 90,000 - 103,000; Full time

Job summary

LeadStack Inc. is seeking a Billing Specialist / Invoice to Cash Support Specialist (L2) on a 1-year contract. You will be the front line for customer billing inquiries, own internal escalations from Sales and GTM, and collaborate across Billing, RevOps, and Support to resolve issues so invoices get paid.

Strong AR, Excel, and SaaS billing knowledge are essential. The role emphasizes customer-facing, resolution-focused work in a fast-paced, remote setting with SLAs and multiple internal

Qualifications

• 2 to 5 years of experience in accounts receivable, billing operations, or high-volume customer operations.
• Experience with a payment processor, ERP, AR automation platform, or ticketing tool (e.g., Stripe, NetSuite, Tesorio, JIRA).
• Exposure to SaaS or usage-based billing models.
• Prior experience in a customer-facing billing, collections, or Tier 2 support function.

Responsibilities

• Serve as a front line for high-volume customer billing and Invoice to Cash questions, resolving each within SLAs from open to close.
• Own internal escalations from Sales and GTM teams, chasing down answers across Billing, Sales Ops, RevOps, Tax, and Support.
• Work directly with customers to resolve issues, obtain missing remittances, clarify details, and send clear, customer-ready responses until the issue is closed.
• Take on research and reconciliation work from Collections and Cash Application, including payment research and unapplied cash investigations.
• Run account reconciliations, tying out customer ledgers across payment processor, billing systems, and the GL when discrepancies arise.
• Spot recurring process or system gaps and call them out for fixes.
• Escalate and track system configuration and engineering fixes to resolution.
• Hands-on, customer-facing experience in accounts receivable, billing operations, order to cash, finance operations, or high-volume customer ops.
• Intermediate Excel or Google Sheets skills, including lookups, pivots, and basic reconciliation logic.
• Experience working a ticket or case queue, managing multiple items at different stages.
• Experience understanding how customer contracts translate into invoices.
• Strong attention to detail, including catching variances and mismatched invoice numbers/dates.
• Clear, professional written communication with customers and internal partners.
• Ability to work from a remote US location and manage your own queue without close supervision.

Skills

Accounts Receivable

Billing Operations

Invoice-to-Cash (I2C)

Account Reconciliation

Payment Investigation

Cash Application

Customer Billing Support

Case / Ticket Queue Management

Microsoft Excel / Google Sheets

Contract-to-Invoice Understanding

ERP / Billing Systems

SaaS / Usage-Based Billing

AI Tools & Workflow Automation

Cross-Functional StakeholderManagement

Problem-Solving & Root Cause Analysis

Tools

Stripe

NetSuite

Tesorio

JIRA

Job description

Client Title : Billing Specialist / Invoice to Cash Support Specialist (L2)

Contract Duration: 1 year (Oct 20, 2026 – Oct 22, 2027)

Pay Rate: $70/hr on W2

Open Positions - 5

About the role:

• Client’ s revenue is scaling at a pace very few finance organizations ever experience, and the Invoice to Cash (I2C) team sits directly in the path of that growth.
• Our Credit, Collections and Cash Application teams manage thousands of customer accounts, and customers come to us with a constant stream of billing questions, reconciliation requests, and payment investigations.
• How quickly and accurately we answer them shapes both the customer experience and how fast invoices get paid. The I2C Support Specialist is a customer-facing, high-volume billing support role.
• You will be a front line for customer billing and Invoice to Cash questions, and you will own internal escalations from Sales and GTM teams end to end. Your job is to research each issue, find the answer, bridge the teams involved, and send the customer a clear response that resolves it so the invoice gets paid. Taking this work on also lets collectors and Cash Application analysts focus on working their accounts. The pace is high.
• Priorities shift daily, case volume is heavy, and questions range from a five-minute lookup to a reconciliation across our payment processor, billing systems, ERP, and several internal teams.
• We are looking for someone who is energized by that variety and relentless about getting to "done."
• This is a customer support and resolution seat, not a portfolio seat. You will not own a collections portfolio or carry a cash target, and you will not own system configuration or engineering fixes; you escalated and track those rather than build them.
• This is also one of the best ventage points in I2C for someone building a finance operations career. You will touch every system, process, and internal team the function works with, which builds the foundation for Collections, Cash Application, Credit, or Billing Ops roles. You will join while the function is being built, not inherited, so the processes you help shape are the ones the organization will run on for years.

Key responsibilities

• Serve as a front line for high-volume customer billing and Invoice to Cash questions, resolving each within team SLAs as the named owner from open to close
• Own internal escalations from Sales and GTM teams, chasing down answers across Billing, Sales Ops, RevOps, Tax, and Support
• Work directly with customers to resolve issues, including obtaining missing remittances, clarifying details, and sending clear, customer-ready responses until the issue is closed
• Take on research and reconciliation work from Collections and Cash Application, including payment research, unapplied cash investigations, and other admin and transactional work, so collectors and analysts can focus on working their accounts
• Run account reconciliations, tying out customer ledgers across our payment processor, billing systems, and the GL when payments, credits, or balances do not match what the customer expects
• Spot recurring process or system gaps and call them out so they can be fixed
• Escalate and track system configuration and engineering fixes to resolution
• Hands-on, customer-facing experience in accounts receivable, billing operations, order to cash, finance operations, or a high-volume customer operations role
• Intermediate Excel or Google Sheets skills, including lookups, pivots, and basic reconciliation logic
• Experience working a ticket or case queue, keeping multiple open items at different stages moving
• Experience understanding how customer contracts translate into invoices
• Strong attention to detail, including catching small variances, mismatched invoice numbers, and dates that do not line up
• Clear, professional written communication with customers and internal partners, including responses someone can act on immediately
• Ability to work from a remote US location and manage your own queue without close supervision

Preferred qualifications

• 2 to 5 years of experience in accounts receivable, billing operations, order to cash, finance operations, or high-volume customer operations
• Experience with a payment processor, ERP, AR automation platform, or ticketing tool (for example Stripe, NetSuite, Tesorio, or JIRA)
• Exposure to SaaS or usage-based billing models
• Prior experience in a customer-facing billing, collections, or tier 2 support function
• Basic familiarity with general ledger concepts and how AR ties to the balance sheet
• A record of getting answers from busy internal partners by being persistent and tactful
• Comfort reprioritizing on the fly when the urgent item at 9am is not the urgent item at 2pm
• A genuine passion for AI, shown by using Claude or similar tools every day to research issues, draft customer responses, and automate manual work, and by constantly looking for new ways AI can make the work faster and better

Key skills :

Accounts Receivable (AR), Billing Operations, Invoice-to-Cash (I2C), Account Reconciliation, Payment Investigation & Cash Application, Customer Billing Support, Case / Ticket Queue Management, Microsoft Excel / Google Sheets, Problem-Solving & Root Cause Analysis, Cross-Functional Stakeholder Management, Customer Communication & Issue Resolution, Contract-to-Invoice Understanding, ERP / Billing Systems, SaaS / Usage-Based Billing, AI Tools & Workflow Automation