Staff Accountant

Tailscale; Canada; Remote; CAD 75,000 - 168,000; Full time

Job summary

A leading tech company is looking for a detail-oriented Staff Accountant to manage the order-to-cash cycle, ensuring compliance and supporting broader accounting processes. The ideal candidate has over 3 years of experience in accounting roles, a solid understanding of SaaS billing models, and familiarity with CRM and ERP systems. This role offers a competitive salary and benefits in a remote-first environment.

Benefits

Competitive total compensation package

Flexible work environment

Comprehensive benefits with no waiting period

Support for personal and professional development

Generous parental leave program

Qualifications

• Experience in fast-paced, remote-first environments.
• Ability to balance detail orientation and collaboration.

Responsibilities

• Serve as primary finance contact for Sales on deal structuring.
• Review transactions for compliance with company policies.
• Support month-end close process and account reconciliations.
• Monitor accounts receivable and assist with collections.

Skills

Order-to-cash processes

SaaS billing models

Accounting principles

CRM (Salesforce)

ERP systems

Organizational skills

Education

3+ years in Accounting, Deal Desk, or Order-to-Cash roles

Strong accounting foundation; CPA a plus

Tools

Salesforce

Stripe

ERP systems

Job description

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more.

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.

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

We strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Our compensation package includes base salary, equity, and comprehensive benefits.

CAN Pay Ranges: $75,040-$167,500 CAD

What We Offer

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package.
• Comprehensive group benefits with no waiting period.
• Remote first company - most of our teams work fully remotely.
• Connect with other Tailscalars IRL.
• Support for your personal and professional development.
• Paid time off and a healthy work-life integration.
• A build-your-own home office setup.
• Generous parental leave program from your first day.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses.