Manager, Contract and Billing

Samsara•Chicago, TX

1d•Remote

About The Position

Samsara is creating a dedicated Contract and Billing Resolution team to handle billing errors, concession requests, and cancellation or return exceptions for Mid-Market and Commercial accounts. The Manager, Contract and Billing will build and lead a new team of 3 to 4 Contract and Billing Resolution Specialists, turning work currently handled by Customer Success Managers and other partners into a repeatable, measurable, and scalable function. This includes establishing the team’s playbook, intake and routing processes, system of record, root-cause reporting, and hiring and coaching practices. The role sits between sales and finance processes. The manager and team will investigate issues across quotes, order forms, contracts, Salesforce segment changes, billing, and invoicing; determine where a problem originated; and work with the teams involved to resolve it. The manager will partner with Customer Success Managers, Sales, Billing Support, Order-to-Cash, Sales Ops, Deal Desk, Finance, and Legal, and report recurring failures to the teams responsible for the underlying systems and processes. This is a remote position open to candidates residing in the United States, except the San Francisco Bay Metro Area, NYC Metro Area, and Washington, D.C. Metro Area.

Requirements

At least 7 years of experience in sales operations, deal desk, contracts, billing operations, order to cash, revenue operations, or a similar finance and operations role.
At least 2 years of people-management experience, ideally in sales operations or finance.
Experience building a team or function from scratch, or leading a major reorganization of an existing team, including creating the playbook and processes that made the work repeatable.
Deep working knowledge of either the quote-to-contract side—including quotes, order forms, amendments, terms, and sales systems that pass contract data downstream—or the billing side, including invoicing, credits, rebills, and collections, and curiosity to learn the other.
Experience setting up or significantly improving a case management, ticketing, or request-routing system, such as Zendesk, Jira, or Salesforce cases, for both customers and internal teams.
Strong investigative skills, including the ability to reconstruct timelines from incomplete or conflicting information across CRM, billing, and contract systems, and teach others to do the same.
Sound financial judgment about credits, concessions, reprocessing, and refunds, with the ability to clearly explain recommendations.
A record of driving results across teams without direct authority, including Sales, Finance, and Operations partners with competing priorities.
Customer-facing communication that remains honest and composed in difficult conversations, and written summaries that enable leaders to make decisions efficiently.
Strong priority management, high emotional intelligence, and comfort with ambiguity and incomplete precedent in a demanding, high-visibility role.

Nice To Haves

Experience across both the sales process and contracting and the finance and billing process.
Experience managing a team handling escalated or high-dollar billing or contract disputes.
Experience with Salesforce, NetSuite, and CPQ tools.
Familiarity with Zendesk, Gainsight, and Sweethawk.
Customer Success, Support, or account management background involving customer-facing financial or contract work.
Experience building dashboards, service levels, or root-cause reporting that changed how other teams improved their processes.
Exposure to subscription or hardware-plus-subscription billing.
Experience using AI tools to drive efficiency and outcomes for oneself and a team.
Strong bias for action and insistence on high standards.

Responsibilities

Hire, onboard, coach, and develop a team of 3 to 4 Contract and Billing Resolution Specialists, setting expectations for case quality, ownership, and customer communication.
Establish the function from scratch by defining the team’s scope and creating a documented, repeatable, and scalable playbook for billing, concession, and cancellation work.
Design and launch a system of record for billing and contract cases with CS Ops and Systems partners, including intake, routing, case tracking, and customer communication in tools such as Zendesk, Salesforce, or Jira.
Ensure every billing, concession, and cancellation request is logged in one place, including requests received through Slack, email, or Gainsight, and coach CSMs and AEs on submitting complete requests.
Serve as the escalation point for complex, sensitive, or high-dollar cases, including delinquent accounts or accounts facing suspension, and engage directly with customers and internal leaders when needed.
Define handoffs, ownership, and service levels with Billing Support, Order-to-Cash, Sales Ops, Deal Desk, Finance, and Legal.
Set standards for distinguishing Samsara errors from concessions, returns, reprocessing, and contract amendments, and for sizing, documenting, and routing concession and cancellation exceptions through the approval matrix.
Build function metrics and reporting, including case volume, days to resolution, repeat errors, concession dollars, and renewal risk tied to billing issues; use the information to manage the team and demonstrate impact.
Ensure root causes are tagged on every case, distinguish one-off issues from systemic failures, and deliver monthly read-outs to teams responsible for relevant systems and processes.
Partner with Support, Finance, Sales Ops, and Product on billing improvements, including earlier detection of billing problems that threaten renewals.
Use AI to improve team workflows, such as structuring case timelines and drafting summaries, while keeping approvals, amounts, and root-cause conclusions with people.
Champion and role-model Samsara’s operating principles, including Keep a High Bar, Be Intellectually Honest, and Solve Problems Together.