Tailscale

Manager, Developer Relations

Canada

Not SpecifiedCompensation
Expert & Leadership (9+ years)Experience Level
Full TimeJob Type
UnknownVisa
Internet Software & ServicesIndustries

Job Description: Developer Advocacy Lead

Position Overview

Tailscale is seeking a technical leader and program scaler to manage its developer advocacy and relations team. This role involves overseeing the strategic direction of developer advocacy, managing a growing team, and scaling developer marketing, relations, and advocacy across North America, Europe, and globally.

This is a player/coach role, requiring both strategic leadership and hands-on contribution, including speaking at conferences, building demos, and representing Tailscale in developer communities. The ideal candidate will have deep empathy for technical users, strong technical skills, systems-thinking and program management capabilities, and a proven track record of scaling developer-facing programs with measurable impact. This individual will be a key custodian of Tailscale's first impression and brand.

Key Responsibilities

  • Lead the team: Manage, mentor, and partner with the Lead Developer Advocate, Senior Community Manager, and Technical Content Manager.
  • Be a voice for Tailscale: Speak at conferences, run workshops, appear in webinars, and create demo-rich content for a global developer audience, with a focus on being Tailscale's leading voice in North America.
  • Scale our programs: Build repeatable programs to grow developer awareness, education, and engagement across key regions.
  • Get us in the right rooms: Improve the talk submission and speaker placement process for relevant conferences in DevOps, security, infrastructure, IT, and more.
  • Measure and grow: Define and track KPIs for developer marketing, relations, and advocacy (e.g., reach, content engagement, brand awareness, community growth, attribution to PLG funnel).
  • Collaborate cross-functionally: Partner with engineering, product, growth, sales, customer success, solutions engineering, and marketing teams to ensure developer initiatives are strategic, measurable, relevant, and high-leverage.
  • Evolve our voice: Help shape Tailscale's presence in the technical world with clarity, authenticity, and technical depth.

What We Are Looking For

  • Proven expertise: Minimum of 5-8+ years in developer-facing roles, including 2+ years in a lead or senior role with a measurable track record of impact.
  • Technical aptitude: Experience using Tailscale and technical depth in networking, infrastructure, security, and/or developer tools.
  • Storytelling: Excellent public speaking and technical storytelling skills, with experience in conference CFP submissions and securing high-visibility speaking slots.
  • Program management: Strong systems-thinking, template creation, and playbook development skills.
  • People management: A strong desire and passion to be a best-in-class people manager, with experience mentoring and developing DevRel talent.
  • International experience: Demonstrated success in growing developer awareness outside of North America and measuring its impact.
  • Outcome-orientation: Familiarity with key Developer Marketing KPIs and a clear perspective on how to track individual and team success.

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.


  • Salary: [Not specified]
  • Location Type: Fully Distributed
  • Employment Type: [Not specified]

Skills

Technical leadership
Program management
Developer advocacy
Public speaking
Content creation
Community engagement
Conference speaking
Demo building
Event organization
Systems-thinking
Technical proficiency with Tailscale

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters
2019Year Founded
$111.9MTotal Funding
SERIES_BCompany Stage
Enterprise Software, CybersecurityIndustries
51-200Employees

Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Unlimited Paid Time Off
Parental Leave
Professional Development Budget
Home Office Stipend
Phone/Internet Stipend
Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.
Cooling venture funding may impact Tailscale's future investment opportunities.
Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.
It integrates with existing identity providers like GSuite and Office365 for easy setup.
Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.
The $100 million Series B funding boosts product expansion and market reach.
Integration with Mullvad enhances privacy with a global VPN server network.

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