Remote opportunity at
TailscaleCommercial Legal Counsel
Tailscale seeks a Commercial Legal Counsel to supply day-to-day commercial legal help during a period of growth. The position is full-time and remote, reporting to the…
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About This Role
Tailscale seeks a Commercial Legal Counsel to supply day-to-day commercial legal help during a period of growth. The position is full-time and remote, reporting to the Head of Legal. Tailscale builds networking software that lets people connect their devices securely, serving users from hobby projects to global enterprises. Founded in 2019, the company operates as a fully distributed team. The counsel handles a wide variety of commercial contracts, such as…
Job Description
Tailscale seeks a Commercial Legal Counsel to supply day-to-day commercial legal help during a period of growth. The position is full-time and remote, reporting to the Head of Legal. Tailscale builds networking software that lets people connect their devices securely, serving users from hobby projects to global enterprises. Founded in 2019, the company operates as a fully distributed team.
The counsel handles a wide variety of commercial contracts, such as deals with enterprise customers, suppliers, alliance partners, marketplaces, technology agreements, data processing terms and confidentiality accords. Much of the job means guiding sales and other revenue-facing groups on how to structure deals, plan negotiations and escalate issues. Templates, negotiation playbooks, fallback language, approval limits and request intake processes are built and refined so contracting can scale.
Collaboration extends to security, privacy and product groups on customer commitments covering data, controls, integrations and AI, and to the finance team and revenue operations on pricing, procurement, insurance and revenue matters. Cross-border deals are part of the scope, and outside lawyers are engaged when niche knowledge is needed. The ideal candidate is a seasoned commercial lawyer who can tell serious exposure from risks that simple safeguards handle, has run talks against experienced counterparties and works without close supervision.
Responsibilities
- Draft, negotiate and manage a broad set of commercial contracts with customers, suppliers, partners, marketplaces, tech vendors, data protection and confidentiality terms
- Guide sales and go-to-market teams on structure, risk and escalation choices
- Present legal questions as clear alternatives so teams can move quickly
- Create and improve templates, playbooks, fallback language, approval limits and self-service tools
- Work alongside security, privacy, product and engineering teams on data, AI and integration commitments
- Work with the finance team and revenue operations on pricing, procurement, insurance and revenue topics
- Handle cross-border transactions and bring in external counsel where specialized knowledge is needed
- Review negotiation trends to shorten cycle times and improve consistency
Requirements
- Law degree plus active bar membership in at least one relevant jurisdiction, or equivalent legal licensing
- Significant experience counseling technology businesses on commercial deals, either in-house or working closely with tech clients
- Background in growing a legal team, contracting function or business process at a startup or fast-growing company
- Good judgment in separating real business exposure from issues that practical controls can handle
- A history of leading talks with sophisticated customers, partners, suppliers or other counterparties
- Clear, brief writing and the ability to earn trust with colleagues in legal, sales and finance as well as security, product and leadership
- Able to work alone, juggle competing priorities and move forward with partial information
Qualifications
- Work involving developer tools, cloud platforms, networking, cybersecurity, SaaS or open-source software
- Experience in enterprise selling, product-led growth, channel alliances, marketplaces, integrations or APIs
- Knowledge of privacy, data protection, security, AI, IP or product advisory topics within technology transactions
- Experience serving international customers or coordinating advice across several legal systems
- Hands-on use of contract lifecycle management software, workflow automation or legal performance metrics
- Mentoring peers, or helping set up how a growing commercial legal team is organized and what it prioritizes
Core Skills
Benefits
- Base pay, equity incentive plan, and group health, vision and dental cover starting immediately with no waiting period
- Retirement matching dollar for dollar up to 0.75 percent of eligible pay
- USD 1,500 per year for professional development, plus mentorship, coaching and internal promotion paths
- Flexible paid time off
- Home-office support: choice of a company laptop (Mac or PC), monthly home internet reimbursement and USD 500 for workstation setup
- Paid parental leave top-ups covering 20 weeks for those giving birth and 16 weeks for other parents
- Annual company retreat and team off-sites
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Where is the role based?
The listing shows the role as remote. Tailscale describes itself as remote first and notes when a role needs in-office work; this role is not marked that way.
What salary range is listed?
The listing shows a base salary range of USD 250,580 to 313,560 per year. The posting body separately gives CAD 250,580 to 313,560 for Canadian candidates, so the currency depends on location.
What experience does the role require?
A law degree with active bar membership, or equivalent authorization, is required. The counsel should also have substantial experience counseling tech businesses on deals and a record of leading negotiations.
Who does the role report to?
The listing names the Head of Legal as the reporting line.
Sample Interview Questions
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