--- title: 'Talent Acquisition Sourcer (Contract) at Tailscale' canonical: 'https://feeny.ai/job/talent-acquisition-sourcer-contract-tailscale-canada-377e7cc46ftz' type: 'job' last_seen: '2026-09-08' --- # Talent Acquisition Sourcer (Contract) at Tailscale - **Company:** Tailscale - **Location:** Canada - **Compensation:** $65–$71/hr - **Work type:** remote - **Posted:** 2026-09-04 - **Last confirmed live:** 2026-09-08 - **Apply:** https://job-boards.greenhouse.io/tailscale/jobs/4731033005 ## Job description ## 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’re looking for an experienced Talent Acquisition Sourcer to help identify and engage exceptional talent as Tailscale continues to scale. This is initially a 6-month contract position with the potential to extend and/or convert to a full-time role based on business needs and performance. You’ll operate as a fully integrated member of our Talent Acquisition team, partnering with Talent Acquisition Partners and hiring teams to build high-quality pipelines across Engineering, Product, Design, GTM, G&A, and other business-critical searches. We’re looking for someone who is curious, resourceful, and creative; can quickly understand new roles and talent markets; and is comfortable going beyond traditional sourcing methods to find and engage exceptional people. ## Key Responsibilities Build & Execute Sourcing Strategies - Partner with Talent Acquisition Partners to understand candidate profiles, hiring priorities, and sourcing needs across the company. - Develop and execute targeted sourcing strategies across Engineering, Product, Design, GTM, G&A, and other functions. - Identify and engage passive talent using a range of sourcing channels, research methods, communities, networks, and creative approaches. - Manage multiple searches and adjust sourcing strategies based on pipeline performance, candidate feedback, and evolving priorities. Source Technical & Specialized Talent - Develop a strong understanding of Tailscale’s product, technology, business, and culture to effectively identify candidates who may thrive here. - Translate technical and specialized role requirements into effective searches in partnership with Talent Acquisition Partners and hiring teams. - Research relevant companies, technologies, communities, and talent pools to identify candidates beyond traditional sources. - Build knowledge of talent markets relevant to Tailscale, including infrastructure, networking, security, developer tools, cloud technologies, and other functional areas. Use Data & Market Intelligence - Bring comfort with sourcing data and market insights to evaluate pipeline health, identify search challenges, and improve sourcing outcomes. - Conduct talent research and market mapping across relevant companies, locations, candidate profiles, and competitive talent pools. - Surface actionable insights on candidate availability, market trends, and search constraints to Talent Acquisition Partners. - Build reusable talent maps and research that can support current and future hiring needs. Build Inclusive Talent Pipelines - Incorporate inclusive sourcing practices into search strategies from the outset. - Identify talent across a broad range of backgrounds, experiences, communities, and career paths. - Explore new networks, communities, and sourcing channels that expand access to qualified talent. - Partner with Talent Acquisition Partners to broaden search approaches and improve candidate representation where appropriate. Engage Exceptional Talent - Create thoughtful, personalized outreach that communicates why Tailscale and the specific opportunity may be compelling. - Build authentic relationships with passive candidates and assess interest, motivation, experience, and potential alignment. - Partner with Talent Acquisition Partners to ensure seamless candidate handoffs and a consistent candidate experience. - Represent Tailscale thoughtfully and authentically in every interaction with prospective talent. Partner Across Talent Acquisition - Collaborate with Talent Acquisition Partners, Sourcers, Operations, and hiring teams on search strategy, candidate calibration, and pipeline development. - Participate in sourcing jams and share sourcing techniques, talent pools, market observations, and search learnings across the team. - Support high-priority or specialized searches as needed, adapting quickly as hiring priorities evolve. - Partner with Talent Acquisition Operations to improve sourcing tools, workflows, data quality, automation, and AI-enabled practices. ## What We Are Looking For - 3+ years of talent sourcing and/or recruiting experience, ideally within high-growth technology companies or similarly competitive talent environments. - Experience sourcing technical talent and supporting searches across multiple functions such as Engineering, Product, Design, GTM, or G&A. - Ability to quickly understand complex or unfamiliar roles and translate candidate requirements into effective sourcing strategies. - Strong research skills and experience using sourcing techniques beyond basic keyword, title, or traditional platform searches. - Strong passive candidate engagement and communication skills, including the ability to create thoughtful, personalized outreach. - Strong organizational and analytical skills, with the ability to manage multiple searches and use sourcing data to evaluate pipeline effectiveness. - Collaborative and adaptable working style, with experience using sourcing platforms, ATS technology, and an interest in AI, automation, and emerging sourcing tools. ## Nice to Have - Experience sourcing within a highly technical startup, developer tools, infrastructure, networking, security, cloud, or similar environment. - Experience identifying technical talent through GitHub, open-source or technical communities, and other channels beyond traditional recruiting platforms. - Experience sourcing across technical and non-technical functions, geographies, or globally distributed teams. - Experience supporting difficult-to-fill, leadership, or confidential searches. - Experience building talent maps, conducting competitive research, or contributing to collaborative sourcing sessions. - A track record of building broad candidate pipelines and finding strong talent through creative research, persistence, and thoughtful engagement. Note: this is a contract position and is not eligible for the full-time, exempt benefits listed below. CAN Pay Range $65—$71 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! - 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. 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. ## About Tailscale ## Company Overview - **One-liner**: Tailscale provides a zero-trust identity-based connectivity platform that replaces legacy VPNs, SASE, and PAM to securely connect remote teams, multi-cloud environments, CI/CD pipelines, edge/IoT devices, and AI workloads. - **Entity Type**: Private (Series B) - **Headquarters**: Toronto, Canada (fully remote, with team members also in the United States and United Kingdom) - **Founded**: 2019 - **Founders**: Avery Pennarun (CEO), David Carney (Chief Strategy Officer), and Brad Fitzpatrick (creator of LiveJournal, Memcached, and OpenID) ## Core Business - **Primary industry/industries**: Secure connectivity, zero-trust networking, VPN replacement, infrastructure security - **Target customers**: B2B – from small businesses and open-source projects to mid-market and enterprise organizations (30,000+ businesses use Tailscale). Also serves developers, IT teams, and DevOps engineers. - **Mission or purpose statement**: “We want to help everyone create their own secure networks built around people and their connections. By making connectivity easier and more secure, we empower teams to build systems that scale, without scaling overhead.” ## Products & Services - **Tailscale (Core Platform)** – A zero-trust mesh overlay network that provides identity-based access to any resource (servers, containers, SaaS tools, cloud instances) without public exposure. Replaces legacy VPNs, bastion hosts, and complex firewall rules. Includes features like SSH, Kubernetes access, database connectivity, and Aperture for securing AI workloads. - **Tailscale Funnel** – Expose local services to the internet securely through Tailscale’s infrastructure. - **Tailscale Serve** – Allow specific devices on a tailnet to serve content publicly or privately. - **Tailscale SSH** – Manage SSH access with identity-based, auditable controls. - **Tailscale Aperture** – Secure access for AI/ML workloads and data pipelines. ## Market Standing - **Valuation/Market Cap**: Not publicly disclosed (private company) - **Key Metric (Funding)**: Total funding of approximately $105M across multiple rounds. Series A ($35M) led by CRV in 2021; Series B ($70M) led by Accel and Insight Partners in 2022. - **Key Metric (Customers)**: 30,000+ businesses use Tailscale. Headcount estimated at ~290 employees as of 2026. - **Notable Investors/Partners**: Accel, CRV, Insight Partners, Heavybit, Uncork Capital. Investors include Amit Kumar (Partner at Accel), Reid Christian (Partner at CRV), Joseph Ruscio (Partner at Heavybit), Rebecca Liu-Doyle (Director at Insight Partners), and Andy McLoughlin (Partner at Uncork). - **Growth Signals**: 25x headcount growth without dedicated IT resources for onboarding; 90% reduction in internal support requests; thousands of hours saved with fewer connectivity issues. Strong adoption in the AI era for securing workloads. ## Competitive Advantages - **Built on WireGuard**: Tailscale is built on the modern, audited, and high-performance WireGuard protocol (wireguard-go), with upstream contributions to the open-source project. - **Zero Trust by Design**: Identity-based access, end-to-end encryption, point-to-point connections (no central VPN server to bottleneck or inspect traffic). User privacy is a fundamental design principle. - **Simplicity & Speed**: “It has to just work” – installation takes minutes, configuration is minimal, and the platform is cross-platform and infrastructure-agnostic. - **Open Source Core**: The core client and server code are open source, and Tailscale offers a free plan for open-source projects, building trust and community. - **Small, Excellent Teams**: The company philosophy is “small is beautiful” – they believe small, excellent teams produce coherent, high-quality outcomes that large teams cannot replicate. ## Strategic Focus - **AI & Multi-Cloud Connectivity**: Tailscale is positioning itself as the secure connectivity platform for the AI era, with specific features (Aperture) for AI workloads. - **Expanding Enterprise Features**: Adding capabilities like Privileged Access Management (SSH, K8s, databases), granular access controls, and audit logging. - **Scaling the Business**: With 30,000+ businesses already onboard, the focus is on converting free/open-source users to paid plans and expanding into larger enterprise accounts. - **Global Hiring**: Actively hiring across engineering (Go, Infrastructure, Security, Mobile), customer success, sales, marketing, and operations in the US, Canada, and UK, with some roles in Singapore. ## Why Work Here - **Fully Remote & Flexible**: Tailscale is a fully remote company with team members across the US, Canada, and UK. Flexible working hours are core to the culture – employees are trusted to manage their time around their lives (family, appointments, etc.). - **Competitive Total Rewards**: Competitive salaries, generous equity incentive plans, group health benefits with no waiting periods, flexible sick days, and an employee assistance program. - **Work-Life Balance**: 26 weeks of paid parental leave, flexible paid vacation, 12 paid company holidays, and a full holiday closure from Dec 24 to Jan 1. - **Workspace Support**: Company-provided laptop (Mac/PC), monthly internet reimbursement, and a “build your own workstation” bonus. - **Engineering Culture**: Strong emphasis on open-source contribution, Go programming, and systems-level engineering. Many team members are active in the Go, NixOS, and SQLite communities. - **Inclusive & Diverse**: The company is committed to diversity and inclusion, with a team not bound by geography, lifestyle, or life stage. They provide accommodations throughout the interview process. - **Interview Process**: For technical roles: Recruiter Interview → Hiring Manager Interview → 2-3 Team Interviews → Technical Working Session → Offer. For non-technical roles: Recruiter → Hiring Manager → 2-3 Team Interviews → Offer. ## Sources 1. [tailscale.com](https://tailscale.com/) – Official website 2. [tailscale.com/company](https://tailscale.com/company) – About page, team, investors, guiding principles 3. [tailscale.com/careers](https://tailscale.com/careers) – Careers page, perks, benefits, culture 4. [job-boards.greenhouse.io/tailscale](https://job-boards.greenhouse.io/tailscale/jobs/4525230005) – Current job openings 5. [jobsbyculture.com](https://jobsbyculture.com/blog/working-at-tailscale-2026) – Employee culture review (2026, ~290 employees) ## Other roles at Tailscale - [Talent Acquisition Sourcer (Contract)](https://feeny.ai/job/talent-acquisition-sourcer-contract-tailscale-united-states-5en4jj8pm7t3) — United States - [Talent Acquisition Coordinator (Contract)](https://feeny.ai/job/talent-acquisition-coordinator-contract-tailscale-united-states-3hz4bnrn5r1j) — United States - [Talent Acquisition Coordinator (Contract)](https://feeny.ai/job/talent-acquisition-coordinator-contract-tailscale-canada-j8ahcy5bbh6f) — Canada - [Talent Acquisition Partner (Contract)](https://feeny.ai/job/talent-acquisition-partner-contract-tailscale-united-states-tyt7n1r4vtpc) — United States - [Talent Acquisition Partner (Contract)](https://feeny.ai/job/talent-acquisition-partner-contract-tailscale-canada-v41jpdhh47hk) — Canada - [Director, APAC Go-to-Market](https://feeny.ai/job/director-apac-go-to-market-tailscale-singapore-bdt02s8r9m1w) — Singapore - [Talent Acquisition Manager](https://feeny.ai/job/talent-acquisition-manager-tailscale-united-states-2vr6fw0aext2) — United States - [Talent Acquisition Manager](https://feeny.ai/job/talent-acquisition-manager-tailscale-canada-j74j1t3pc2hn) — Canada - [Talent Acquisition Sourcer](https://feeny.ai/job/talent-acquisition-sourcer-tailscale-united-states-mrdq3rmbykac) — United States - [Talent Acquisition Sourcer](https://feeny.ai/job/talent-acquisition-sourcer-tailscale-canada-wgmy5f9g4ney) — Canada