Director of Data

Tailscale; Canada; Remote; CAD 297,000 - 366,000; Full time

Job summary

Tailscale is seeking a Director of Data to enhance its data engineering and analytics functions. This leadership role demands experience in building data infrastructure, optimizing workflows, and partnering with various teams to drive data-driven decisions across a scaling technology company.

Benefits

Flexible work environment

Comprehensive health benefits

Annual professional development budget

Paid time off program

Remote work opportunity

Qualifications

• Experience in scaling data infrastructure and teams in a fast-growing startup.
• Deep understanding of modern data architectures and pipeline design.
• Hands-on experience with tech stack like Snowflake, dbt, Fivetran, Looker.

Responsibilities

• Lead and grow a team of data professionals.
• Define and execute the strategic roadmap for data infrastructure.
• Oversee scalable data pipelines and data quality frameworks.

Skills

Data engineering

Analytics engineering

Business acumen

Team leadership

AI/ML technologies

Data governance

Tools

Snowflake

dbt

Looker

Fivetran

Job description

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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 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.

Job Description

Tailscale is looking for a Director of Data to build our data engineering, analytics engineering, data analysis, and data science functions. In particular, we are looking for a leader with strong data engineering and analytics engineering experience and who has solid business acumen. This leader would help lead our data organization and design and build our data infrastructure to support data-driven decision-making across product, engineering, marketing, operations, finance, support, sales, etc. This role will report to the SVP of Operations.

As Tailscale continues to scale, we are expanding our data infrastructure to support growing operational complexity. This includes consolidating data from multiple sources into reliable pipelines, building robust reporting and monitoring, leveraging modern data engineering best-practices and technologies to optimize workflows and outputs, and creating the data governance frameworks needed to support product development at scale. This is a hands-on leadership role ideal for someone who enjoys building and prototyping alongside their team, can architect systems, write code, and also lead and mentor.

The ideal candidate will have experience with a modern data stack and knows how to move through the challenges of scaling data at a fast growing technology company. The ideal leader will be forward thinking in how not just to build a data function of the past but one that includes modern tools including new AI tools and formats to build in a function that will empower end-users in their decision making.

Key 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.
  
  

What We Are Looking For:

• 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
  
  

Nice to Have:

• 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
  
  

Our Tech Stack:

Snowflake, DBT, Hightouch, Fivetran, RudderStack, Looker, Grafana, Stripe, Salesforce, HubSpot, 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 Ranges

$297,480—$365,820 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!
• 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.
  
  

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.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Information Technology

• Industries

  Software Development

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