Executive Business Partner, Engineering

Job Description

About Tailscale

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 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

We’re looking for an experienced Executive Business Partner to partner with our VP of Engineering. You will also work closely with the Chief of Staff, CTO.

You’ll serve as a trusted partner to the VP of Engineering helping them stay focused on the work that matters most. By connecting people, priorities, and decisions across Engineering, Product, Design, Finance, Legal, People, Operations, Marketing, and the Executive Leadership Team, you’ll keep initiatives moving, remove operational friction, improve day-to-day execution, and ensure nothing important falls through the cracks. You’ll thrive in ambiguity, exercise sound judgment, and proactively solve problems before they become distractions.

The ideal candidate enjoys operating systems, thrives in fast-moving environments, communicates exceptionally well, and takes pride in making everyone around them more effective.

Key Responsibilities

Executive Partnership

• Partner closely with the VP of Engineering to maximize their effectiveness and protect their time managing their calendars, incoming and outgoing requests, and reconciling conflicts
• Build a deep understanding of executive priorities, organizational goals, and business context to proactively identify opportunities and risks.
• Anticipate needs before they’re expressed and independently solve problems with minimal direction.
• Act as a trusted extension of the executives while exercising exceptional judgment and discretion.

Executive Operations

• Own complex calendar management across multiple time zones while balancing competing priorities and continuously optimizing executive time.
• Manage meeting preparation, agendas, briefing documents, attendee coordination, and follow-up to ensure every meeting has clear purpose and outcomes.
• Coordinate recurring department meetings, planning sessions and department offsites which will include an annual cross-department offsite and various smaller events throughout the year.
• Track commitments, key decisions, action items, and cross-functional dependencies to ensure timely execution on behalf of the executive(s)
• Prepare presentations, executive communications, spreadsheets, reports, and briefing materials for internal and external audiences.
• Help prepare executives for board meetings, customer meetings, leadership presentations, conferences, and speaking engagements.
• Partner with the Chief of Staff to the CTO in coordination of work.

Cross-Functional Coordination

• Partner closely with leaders across Engineering, Product, Design, People, Finance, Legal, Marketing, IT, and Operations.
• Build strong working relationships across the company and serve as a trusted point of coordination for executive priorities.
• Partner with other Executive Assistants

Project & Program Management

• Partner with Executive on deliverables such as headcount planning and department budgets
• Partner with Executive on operating the performance review process
• Improve administrative and operational processes by identifying inefficiencies and implementing scalable solutions.
• Build (where necessary) and operate repeatable systems that improve organizational effectiveness as the company grows.

Travel & Logistics

• Coordinate complex domestic and international travel, including itineraries, accommodations, visas (when applicable), transportation, and contingency planning.
• Manage executive expense reporting accurately and efficiently.
• Coordinate department offsites, team gatherings, planning sessions, and company events.

Continuous Improvement

• Continuously evaluate executive workflows and identify opportunities to improve efficiency.
• Leverage AI-powered and modern productivity tools to streamline administrative work, automate repetitive tasks, and improve organizational effectiveness.
• Recommend and implement new processes that improve collaboration across the department

What We Are Looking For

• Significant experience supporting VP- or C-level executives within a fast-paced technology company
• Experience supporting Engineering, Product, Design, or other highly technical organizations
• Experience working with Google Suite, Notion, Slack, Zoom and Jira
• Demonstrated success operating independently with minimal direction in rapidly changing environments
• Exceptional organizational and project management skills with the ability to manage multiple competing priorities simultaneously
• Outstanding written and verbal communication skills
• Strong business judgment and the ability to make thoughtful decisions while knowing when to escalate
• Proven ability to anticipate executive needs and proactively remove obstacles
• Excellent attention to detail while maintaining perspective on broader business priorities
• Experience coordinating complex cross-functional projects involving senior stakeholders
• High emotional intelligence with the ability to build trusted relationships across all levels of an organization
• Comfortable navigating ambiguity and adapting quickly as priorities evolve
• Strong systems thinking with a continuous improvement mindset
• Absolute integrity and discretion when handling confidential information
• Comfortable working asynchronously in a globally distributed remote organization
• A collaborative, humble approach with a willingness to help wherever needed

Nice to Have

• Experience working in a high-growth SaaS, infrastructure software, developer tools, or security company
• Experience supporting distributed global organizations
• Experience planning executive offsites, leadership retreats, and company events
• Experience implementing workflow automation or leveraging AI tools to improve productivity
• Experience supporting executive communications, board preparation, or company planning processes

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

$144,800—$217,100 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

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.