Staff Accountant

Tailscale is growing, and we’re looking for a detail-oriented and collaborative Staff Accountant to join our Finance & Accounting team. In this role, you’ll oversee the full order-to-cash cycle — serving as the primary liaison with Sales to review and approve deals, ensuring they flow cleanly into billing, collections, and revenue recognition. You’ll also support broader accounting processes, contributing to monthly close, reconciliations, revenue recognition, and general financial reporting. This is an opportunity to play a pivotal role in building scalable financial operations, balancing the need for compliance and accuracy with the agility required in a fast-growing SaaS business. Key Responsibilities Serve as the first point of contact from finance for Sales on deal structuring, order processing, and approvals. Review and approve transactions to ensure compliance with company policies, contractual guidelines, and revenue recognition standards. Maintain accurate deal setup in CRM, billing, and ERP systems to enable invoicing and revenue recognition. Support the month-end close process, including revenue recognition in accordance with ASC 606 and account reconciliations. Partner cross-functionally with Sales, Customer Success, and Legal to streamline workflows and reduce friction in the deal-to-cash process. Monitor accounts receivable, support collections efforts, and help resolve billing disputes. Assist with internal controls, process documentation, and audit support as needed. Identify and implement improvements to increase efficiency and accuracy across order-to-cash and accounting processes. What We Are Looking For 3+ years of experience in Accounting, Deal Desk, or Order-to-Cash roles at SaaS high-growth startups Solid understanding of order-to-cash processes, SaaS billing models, and ASC 606 revenue recognition principles Experience with CRM (Salesforce), billing platforms (Stripe), and ERP systems Strong accounting foundation; CPA a plus Excellent organizational skills, with the ability to balance detail orientation and cross-functional collaboration Self-starter with an entrepreneurial mindset; comfortable working in a fast-paced, remote-first environment