Job Details

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
• As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. 
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. 
• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! 
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. 
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.