Contract and Billing Specialist

Overview

This role is part of the Customer Success organization and focuses on business value delivery by helping customers adopt the platform, realize measurable outcomes, and renew and expand with confidence.

Billing errors, concession requests, and cancellation or return exceptions currently involve multiple teams. This position serves as the single owner for complex billing and contract cases for Mid-Market and Commercial accounts, reducing repeat issues and ensuring cases move efficiently through to a confirmed fix.

Responsibilities

• Own complex billing and contract cases for Mid-Market and Commercial accounts, from initial report through a confirmed fix, and keep the customer informed in plain terms, including when accounts are delinquent or facing suspension.
• Reconstruct the end-to-end story behind billing errors across contracts, order forms, segment or ownership changes, reprocessing, and invoicing—including cases with multiple AE handoffs and no clear record of what was promised.
• Determine whether the issue is a correction of a company error versus a concession, return, reprocess, or contract amendment, and choose the path that fixes the customer’s billing issue (not only the immediate complaint).
• Coordinate execution across Billing Support, Order-to-Cash, Sales Ops, Deal Desk, Finance, and Legal.
• Evaluate and prepare concession requests:
  • Confirm whether the company was at fault
  • Size the request against policy and the approval matrix
  • Write a short case summary that includes what happened, root cause, options considered and ruled out, recommendation, and risk
  • Route to the correct approver and confirm credit is applied and communicated to the customer.
• Support cancellation, return, and ETF exceptions by:
  • Validating eligibility (purchase and renewal dates, trial history, Return ACV, financing partner, documentation)
  • Preparing the case for the approving team
  • Acting as Customer Success fallback when the first approver does not respond within the window
  • Ensuring approved outcomes are processed.
• Serve as the primary front door for billing, concession, and cancellation requests:
  • Log every request in a single case record (including requests that arrive via Slack, email, or Gainsight)
  • Route requests to the appropriate resolution path
  • Coach CSMs and AEs on what a complete request looks like.
• Fix repeat causes by tagging root cause on every case, distinguishing one-offs from systemic failures, and delivering a monthly read-out to the teams that own the systems and processes involved.
• Carry forward billing improvement work with Support, Finance, and Product, including earlier detection of billing problems that threaten renewals.
• Model and embed operating principles while scaling, including keeping a high bar, being intellectually honest, and solving problems together.

Requirements

• 4+ years of experience in billing operations, order to cash, revenue operations, deal desk, contracts, or a similar finance and operations role.
• Strong priority management and high emotional intelligence for a high-visibility, demanding position.
• Strong investigative skills, including rebuilding timelines from incomplete or conflicting information across CRM, billing, and contract systems (including when people involved have left).
• Sound financial judgment regarding credits, concessions, reprocessing, and refunds, with the ability to clearly explain recommendations.
• Customer-facing communication that remains honest and composed during difficult conversations, including written summaries that leaders can quickly review.
• Demonstrated ability to drive results across teams without direct authority, working to deadlines in an approval process.
• Familiarity with order forms, amendments, and terms, and how these flow into billing.
• Comfort operating in ambiguity with incomplete precedent, along with rigorous case management so nothing falls through the cracks across weeks and stakeholders.
• Diplomacy, tact, and poise under pressure when working through customer issues.

Preferred Qualifications

• Experience handling escalated or high-dollar billing disputes.
• Experience with Salesforce, NetSuite, or an equivalent ERP, and CPQ tools. Also used: Zendesk, Gainsight, and Sweethawk.
• Customer Success, Support, or account management background involving customer-facing financial or contract work.
• Experience building or improving billing dispute processes.
• Exposure to subscription or hardware-plus-subscription billing.
• Experience using AI tooling to drive efficiency and outcomes.
• Strong bias for action and high standards.

Compensation & Benefits

• Annual Base Salary: $84,787.50—$128,250 USD (full-time employees).
• Base pay may vary based on factors including city of residence, job-related knowledge, skills, and experience.
• Total rewards include base salary, performance-based bonus/variable pay, and equity for eligible roles, plus additional benefits such as a flexible, employee-led remote model, a professional development stipend, and comprehensive health and parental leave plans.

Location

• Remote position open to candidates residing in the US except the San Francisco Bay Metro Area, NYC Metro Area, and Washington, D.C. Metro Area.
• Relocation assistance will not be provided for this role.
• Offers are contingent upon the individual’s ability to secure and maintain the legal right to work at the company and in the specified work location, if applicable.

Equal Employment Opportunity & Accommodations

• The employer provides equal employment opportunities to qualified applicants without regard to protected characteristics.
• Reasonable accommodations are available for applicants who require them during the recruiting process.