Staff Accountant

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About Tailscale

Tailscale is making safe connection effortless 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 building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

Tailscale is growing, and we’re looking for a detail-oriented, operationally minded, and collaborative Staff Accountant to join our Finance & Accounting team. In this role, you’ll support core accounting operations across order-to-cash, accounts receivable, billing, and the monthly close, while owning select day-to-day accounting processes. You’ll work closely with the broader Accounting team to help ensure transactions are processed accurately, issues are resolved quickly, and our financial operations continue to scale effectively as the business grows.

You’ll partner closely with Sales, Deal Desk, Customer Success, Legal, and other members of Finance to help ensure deals are structured and processed accurately from contract review through billing and accounting. You’ll also contribute to monthly and quarterly close activities, account reconciliations, revenue-related processes, and other operational accounting initiatives.

This is an opportunity to take ownership of critical day-to-day accounting processes while helping us continue to build scalable, well-controlled financial operations for a fast-growing SaaS business.

Key Responsibilities

• Support the order-to-cash process from deal approval through invoicing, collections, and accounting. Review order forms and commercial terms, including payment terms, billing frequency, credits, discounts, and other non-standard terms, and partner closely with Sales, Deal Desk, Customer Success, Legal, and Finance to resolve issues that could impact contract execution, billing, collections, or accounting treatment.
• Support recurring invoicing and billing activities, including month-end and quarter-end billing, renewals, usage-based charges, and customer adjustments.
• Support monthly and quarterly close activities, including journal entries, accruals, reconciliations, and balance sheet support.
• Monitor accounts receivable, support collections, investigate aging balances, and help resolve customer billing and payment disputes.
• Support revenue-related accounting processes and maintain sufficient documentation to support revenue recognition under ASC 606.
• Support employee expense reimbursement operations, including review, processing, policy compliance, and issue resolution as needed.
• Identify and implement process improvements across Deal Desk, billing, collections, expense reimbursements, and close activities.

What We Are Looking For

• 3+ years of progressive accounting experience, preferably in a high-growth SaaS or technology environment.
• Strong accounting foundation with experience supporting monthly and quarterly close processes, reconciliations, journal entries, and accruals.
• Experience with order-to-cash processes, including customer contracts, invoicing, accounts receivable, collections, and billing operations.
• Working knowledge of ASC 606 and an understanding of how commercial terms can impact billing and revenue recognition.
• Experience partnering cross-functionally with Sales, Deal Desk, Customer Success, Legal, or similar teams.
• Experience with ERP, CRM, billing, and expense management systems; familiarity with NetSuite, Salesforce, Stripe, DealHub, Ramp, or similar platforms is a plus.
• Strong analytical, organizational, and communication skills, with the ability to manage recurring responsibilities alongside close deadlines.
• Bachelor’s degree in Accounting, Finance, or a related field; CPA or progress toward CPA certification is a plus.

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.

CAN Pay Range

$115,240—$143,380 CAD

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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
• 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

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. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.