Director of Data

Summary

Join Tailscale as the Director of Data to build and lead data engineering, analytics engineering, data analysis, and data science functions. You will design and build data infrastructure to support data-driven decision-making across various departments. This hands-on leadership role requires experience with a modern data stack and scaling data in a fast-growing tech company. You will lead a team, define a strategic roadmap, and implement scalable data pipelines and solutions. The ideal candidate possesses strong technical skills, excellent communication, and a proven ability to create and execute long-term data strategies.

Requirements

• Experience scaling data infrastructure and teams in a fast-growing startup environment, with a track record of building and leading technical talent
• Deep understanding of modern data architectures, data modeling, and pipeline design with strong technical judgement for system optimization
• High curiosity, growth mindset, and experimentation orientation around AI and the intersection of AI and data infrastructure
• Proven ability to create and execute long-term data strategy while delivering immediate business impact. You think big, start small, and ship fast. You’re eager to test what’s new and know when to standardize what works. You have built systems that have scaled
• Hands-on experience with our tech stack (Snowflake, dbt, Fivetran, Looker) or similar modern data tools. You’re pragmatic, curious, and always learning
• Excellent communication skills, with the ability to translate technical concepts for business stakeholders and frame data capabilities as solutions for enabling business objectives
• High ownership mentality and bias towards action, comfort with ambiguity, and strong commitment to driving results
• Track record of excellent people management, especially as it relates to hiring and developing talent

Responsibilities

• Lead, develop, and grow a team spanning data engineering, analytics engineering, data analysts, and data scientists
• Define and execute the strategic roadmap for data infrastructure and analytics capabilities across the organization
• Oversee the design and implementation of scalable data pipelines, data models, analytics solutions, and business intelligence tooling
• Establish data governance frameworks, quality standards, and unified data models across operational and product use cases
• Partner cross-functionally with Sales, Marketing, Engineering, Finance, and Product teams to understand and address data needs including reporting
• Expose Tailscale’s data to departments via a self service solution for Tailscaler’s to make high impact decisions
• Optimize data flows and quality across key business systems (Salesforce, Stripe, Jira, etc.) and downstream analytics platforms (Looker, Grafana, Hightouch, etc.)
• Identify opportunities to leverage ultra modern AI/ML technologies to enhance product and business intelligence, internal tooling, and customer experience

Preferred Qualifications

• B2B SaaS experience, both with PLG and sales-led business models
• Experience with usage-based products and or a draw down pricing model
• Experience with data platforms at high-growth companies
• Experience with billing systems, financial reporting, and compliance requirements
• Experience with unstructured data integrations and log processing

Benefits

• 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!
• All-remote with the opportunity to work from anywhere —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)
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK
• 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 $1000 USD to customize your workstation to make it your own
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks