[Remote] Staff Accountant at Tailscale

United States

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Not SpecifiedCompensation

Senior (5 to 8 years)Experience Level

Full TimeJob Type

UnknownVisa

SaaS, TechnologyIndustries

Requirements

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

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

Skills

Key technologies and capabilities for this role

Revenue RecognitionASC 606Month-End CloseAccount ReconciliationsOrder-to-CashCRMERP SystemsAccounts ReceivableBillingCollections

Questions & Answers

Common questions about this position

What is the salary range for the Staff Accountant position?

This information is not specified in the job description.

Is this a remote position?

Yes, the role is in a remote-first environment, and the company is fully distributed.

What experience and skills are required for this role?

Candidates need 3+ years in Accounting, Deal Desk, or Order-to-Cash at SaaS startups, understanding of order-to-cash processes, SaaS billing, ASC 606, experience with CRM (Salesforce), billing platforms (Stripe), ERP systems, strong accounting foundation (CPA a plus), organizational skills, and cross-functional collaboration.

What is the company culture like at Tailscale?

Tailscale is fully distributed, remote-first, fast-paced, and values collaboration, an entrepreneurial mindset, detail-orientation, and building scalable operations in a high-growth SaaS environment.

What makes a strong candidate for this Staff Accountant role?

A strong candidate has 3+ years in SaaS accounting or order-to-cash, expertise in ASC 606 and SaaS billing, experience with Salesforce, Stripe, and ERP systems, plus a CPA, organizational skills, and an entrepreneurial mindset for remote, cross-functional work.

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters

2019Year Founded

$111.9MTotal Funding

SERIES_BCompany Stage

Enterprise Software, CybersecurityIndustries

51-200Employees

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Flexible Work Hours

Remote Work Options

Unlimited Paid Time Off

Parental Leave

Professional Development Budget

Home Office Stipend

Phone/Internet Stipend

Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.

Cooling venture funding may impact Tailscale's future investment opportunities.

Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.

It integrates with existing identity providers like GSuite and Office365 for easy setup.

Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.

The $100 million Series B funding boosts product expansion and market reach.

Integration with Mullvad enhances privacy with a global VPN server network.

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