Director of Data, Tailscale
$172-215k
+ Equity
More information about location
A zero config VPN for building secure networks
Open for applications
A zero config VPN for building secure networks
101-200 employees
Open for applications
$172-215k
+ Equity
More information about location
101-200 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- Exceptional leadership skills with a track record of building and mentoring high-performing data teams
- Experience in a variety of data and product management roles, with material experience in a leadership position overseeing data teams and initiatives
- Deep understanding of data architecture, data modeling, and database technologies (e.g. SQL, NoSQL, dbt, Fivetran)
- Proven experience in setting up and managing data warehouses, lakes, and data analytics platforms (e.g. Snowflake)
- Strong knowledge of data governance, data quality management, and data protection laws and regulations (e.g. GDPR, CCPA)
- Experience with data analytics and visualization tools (e.g. Looker, Grafana) and familiarity with machine learning frameworks
- An advanced degree (or equivalent experience) in Data Science, Computer Science, Information Technology, or a related field
- Excellent communication and stakeholder management skills, capable of conveying complex data concepts in simple terms
What the job involves
- The Director of Data at Tailscale will be the visionary and executor behind our data infrastructure and strategy
- This pivotal role involves overseeing the collection, storage, management, quality, and security of data across the company
- You will lead a team responsible for turning data into critical insights that inform strategic decisions and product enhancements
- Your leadership will ensure that Tailscale's data ecosystem supports our growth, innovation, and operational needs effectively and securely
- This role will report to Tailscale’s COO
- You will be leading a small yet very impactful data team consisting of three analytics engineers and one data engineer
- This role has a broad responsibility overseeing the organization's entire data ecosystem, including data strategy, architecture, governance, and analytics
- Your purview would not only encompass analytical insights, but also the creation and maintenance of robust data infrastructures, data quality, and compliance with data protection regulations
- Develop and execute the company's data strategy, optimizing data collection, storage, analysis, and governance processes to drive business growth
- Build, mentor, and empower a high-performing team of data professionals, including analysts, engineers, operations roles, and data scientists, to drive innovation and deliver impactful results
- Engineer and implement robust data infrastructure and pipelines, ensuring seamless and secure data flow throughout the organization to support critical business operations
- Establish and uphold stringent data governance and quality standards, ensuring regulatory compliance (e.g., GDPR, CCPA) and safeguarding sensitive information
- Collaborate cross-functionally to understand and address departmental data requirements, aligning data initiatives with overarching business objectives to maximize value
- Champion the adoption of advanced analytics, machine learning models, and data visualization tools to drive informed decision-making and fuel product innovation
- Coordinate, connect, and align the sales and marketing systems that support go-to-market motions
- Effectively communicate data-driven insights and narratives to stakeholders at all levels, fostering a culture of data literacy and informed decision-making across the organization
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received with reviewers agreeing that it is easy to set up and a great tool for developers. The company plan to develop its product further by tackling the complexity of software and confront operational problems that people face daily. The company continues its expansion by empowering small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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