Headquarters: Remote (Canada)
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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
We are looking for an Analytics Engineer who thrives in high-complexity environments—someone excited to bring clarity to chaos, untangle complex models, and lay down the foundation for scalable solutions.
This is a hands-on, high-impact role for someone who isn’t afraid to address manual processes, viewing them as opportunities to build scalable solutions that drive meaningful impact. You’ll work closely with stakeholders across the company to build reliable, trusted data models that support reporting, analysis, and decision-making.
Key Responsibilities
- Dive into complex systems and manual workflows to develop an understanding of our tools and constraints.
- Thoughtfully design and maintain clean, scalable, production-grade dbt models (e.g., ARR, revenue recognition).
- Work across the full data pipeline, from ingestion to transformation to visualization.
- Take a pragmatic approach to system challenges, balancing quick fixes with thoughtful long-term design.
- Collaborate with Finance, Engineering, Sales, and other teams across the company to understand data needs and deliver timely, practical solutions.
What We Are Looking For
- Experience designing and maintaining production-grade data models and pipelines.
- Deep understanding of modern data modeling principles and best practices.
- Strong SQL skills and confidence working with complex datasets and schemas.
- High attention to detail, with high standards for data accuracy and validation.
- Flexibility and resourcefulness in navigating manual tasks or imperfect systems.
- Passion for clean code, scalable architecture, and incrementally reducing complexity over time.
- Ability to manage time, prioritize effectively, and thrive in a fast-moving environment.
- Clear communication skills with both technical and non-technical collaborators.
- Willingness to flexibly support other domains (e.g., Product, Marketing, and Engineering) as the team grows.
Nice to Have
- Experience at a high-growth PLG SaaS company.
- A track record of transforming manual, ad hoc workflows into scalable data pipelines.
- Familiarity with billing systems, GAAP accounting, revenue recognition, or audit support.
- Exposure to Stripe, Salesforce, or Orb in billing and finance contexts.
- Familiarity with financial cycles and the need for fast iteration during month- and quarter-end.
Our Tech Stack
- Snowflake, dbt, Hightouch, Fivetran, Looker, Stripe, Salesforce, Orb.
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 $203,680 — $254,600 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.