Contract and Billing Specialist

Overview

This role helps customers resolve complex billing and contract issues efficiently, supporting business value delivery and renewal confidence. Cases such as billing errors, concession requests, and cancellation or return exceptions currently involve multiple teams and can repeat for the same reasons—lengthening resolution times and pulling focus away from adoption and renewal work.

As the Contract and Billing Resolution Specialist, you will serve as the single owner of complex billing and contract cases for Mid-Market and Commercial accounts, investigating what happened across systems and teams and driving fixes to completion while keeping customers informed.

Responsibilities

• Own complex billing and contract cases for Mid-Market and Commercial accounts, from first report through confirmed fix, including accounts that are delinquent or facing suspension.
• Reconstruct the full story behind billing errors across contracts, order forms, segment or ownership changes, reprocessing, and invoicing, including cases with several AE handoffs and no clean record of what was promised.
• Distinguish between a Samsara error versus a concession, a return, a reprocess, and a contract amendment, selecting the path that fixes the customer’s billing (not only the immediate complaint).
• Coordinate cross-functional execution with Billing Support, Order-to-Cash, Sales Ops, Deal Desk, Finance, and Legal to implement the fix.
• Evaluate and prepare concession requests by:
  • Confirming whether Samsara was at fault
  • Sizing the request against policy and the approval matrix
  • Writing a short case summary including what happened, root cause, options considered and ruled out, recommendation, and risk
  • Routing to the appropriate approver and confirming credit is applied and the customer is informed
• 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, and ensuring approved outcomes are processed.
• Serve as the front door for billing, concession, and cancellation requests by:
  • Logging every request in a single case record (including requests arriving via Slack, email, or Gainsight)
  • Redirecting requests to the right path
  • Coaching Customer Success Managers and Sales representatives on what constitutes a complete request
• Reduce repeat causes by:
  • Tagging root cause on every case
  • Separating one-offs from systemic failures
  • 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, including Keep a High Bar, Be Intellectually Honest, and Solve Problems Together, as the organization scales.

Minimum Qualifications

• 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.
• Strong investigative skills, including rebuilding a timeline from incomplete or conflicting information across CRM, billing, and contract systems, even when people involved have left.
• Sound financial judgment about credits, concessions, reprocessing, and refunds, with the ability to clearly explain recommendations.
• Customer-facing communication that remains honest and composed in difficult conversations, including written summaries a leader can review and decide on.
• Proven ability to drive results across teams without direct authority, including working to deadlines within an approval process.
• Familiarity with order forms, amendments, and how they flow into billing.
• Comfort with ambiguity and incomplete precedent, plus rigorous case management so issues do not fall through over weeks and stakeholders.
• Diplomacy, tact, and poise under pressure.

Preferred Qualifications

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

Compensation & Benefits

• Annual base salary range (full-time): $84,787.50—$128,250 USD
• Total rewards include base salary, performance-based bonus/variable pay, and equity for eligible roles in a high-growth public company.
• Additional benefits may include a flexible, employee-led remote model, a professional development stipend, comprehensive health coverage, 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 is not provided.
• Offers of employment 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.