--- title: 'Talent Acquisition Manager at Tailscale' canonical: 'https://feeny.ai/job/talent-acquisition-manager-tailscale-canada-j74j1t3pc2hn' type: 'job' last_seen: '2026-09-08' --- # Talent Acquisition Manager at Tailscale - **Company:** Tailscale - **Location:** Canada - **Compensation:** $212k–$264k - **Work type:** remote - **Posted:** 2026-08-31 - **Last confirmed live:** 2026-09-08 - **Apply:** https://job-boards.greenhouse.io/tailscale/jobs/4728965005 ## 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 Manager to lead and develop a high-performing team of Talent Acquisition Partners while partnering with business leaders to deliver exceptional hiring outcomes. This is a hands-on people leadership role responsible for recruiting performance across one or more business functions, such as Engineering, Product & Design or GTM & G&A. You’ll coach and develop Talent Acquisition Partners, translate business priorities into recruiting strategies, and ensure the team operates as trusted advisors to hiring leaders while consistently delivering against hiring goals. You’ll partner closely with Talent Acquisition Operations and Sourcing, which provide the programs, systems, analytics, sourcing expertise, and operational infrastructure that enable recruiting success. We’re looking for a leader who brings strong recruiting judgment, business acumen, and a data-informed approach and thrives in a fast-moving environment where priorities evolve. ## Key Responsibilities Lead & Develop Talent Acquisition Partners - Lead, coach, and develop a team of Talent Acquisition Partners through clear expectations, ongoing feedback, career development, and performance management. - Coach Partners to strengthen recruiting strategy, stakeholder management, candidate assessment, influencing, negotiation, and closing capabilities. - Foster a culture of accountability, collaboration, inclusion, strong judgment, and continuous improvement. - Build team capability and adapt priorities, coverage, and ways of working as business and hiring needs evolve. Drive Recruiting Strategy & Performance - Translate business priorities and hiring plans into actionable recruiting strategies, team priorities, and execution plans. - Establish a high bar for recruiting excellence and ensure consistent execution, from intake and search strategy through candidate assessment, offer, and close. - Review search performance, pipeline health, hiring velocity, and team capacity to identify risks and drive accountability for outcomes. - Provide guidance and hands-on support for complex, high-priority, or executive searches when needed. Partner with Business Leaders - Build trusted relationships with senior leaders and serve as a strategic advisor on hiring priorities, talent markets, workforce needs, and recruiting strategy. - Help leaders navigate talent availability, hiring tradeoffs, timelines, and market realities while maintaining a consistently high hiring bar. - Proactively identify hiring risks and partner with Talent Acquisition Partners and business leaders to develop solutions. - Create accountability around effective hiring practices, timely decision-making, interview quality, and candidate experience. Use Data & Market Intelligence - Bring expertise and comfort with recruiting data and market insights to assess performance, identify hiring risks, and improve team and search outcomes. - Use pipeline, funnel, hiring velocity, capacity, and market data to identify trends and guide recruiting priorities and decisions. - Translate recruiting performance and talent market insights into actionable recommendations for Talent Acquisition and business leaders. - Partner with Talent Acquisition Operations to ensure reporting and analytics effectively support team performance and business decision-making. Partner Across Talent Acquisition - Collaborate closely with Sourcing, Talent Acquisition Operations, and TA leadership to align recruiting strategies, resources, and priorities with business needs. - Partner with Sourcing on pipeline strategy and difficult-to-fill talent needs, and with TA Operations on processes, systems, analytics, enablement, and technology adoption. - Share business and recruiter feedback to improve recruiting programs, tools, workflows, and AI-enabled practices. - Contribute to broader Talent Acquisition initiatives that improve candidate experience, team effectiveness, and scalability. ## What We Are Looking For - 8+ years of full-cycle recruiting experience supporting technical and/or business organizations in high-growth technology environments, including 2–5+ years leading and developing recruiting teams. - Demonstrated success coaching experienced Talent Acquisition Partners, setting clear expectations, managing performance, and building high-performing teams. - Proven ability to partner with senior business leaders as a trusted advisor, using strong judgment and consultative skills to influence hiring strategies and decisions. - Strong recruiting expertise and business acumen, with the ability to translate organizational priorities and hiring plans into effective recruiting strategies and team execution. - Strong analytical skills and comfort using recruiting data, market intelligence, and performance metrics to identify challenges, drive accountability, and improve hiring outcomes. - Ability to lead through ambiguity, balance strategic priorities with hands-on leadership, and adapt team focus as business needs evolve. - Strong communication, coaching, and stakeholder management skills, with experience partnering effectively across Sourcing, Talent Acquisition Operations, and other cross-functional teams. ## Nice to Have - Experience leading recruiting across multiple functions, including Engineering, Product, Design, GTM, and/or G&A. - Experience helping scale recruiting and organizational growth within a high-growth technology company. - Experience partnering closely with dedicated Sourcing and Talent Acquisition Operations teams to improve recruiting effectiveness and scalability. - Experience hiring globally across North America, EMEA, and/or APAC. - A track record of developing strong recruiters into trusted business advisors while consistently delivering against ambitious hiring goals. 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 Range $211,720—$263,980 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 Sourcer (Contract)](https://feeny.ai/job/talent-acquisition-sourcer-contract-tailscale-canada-377e7cc46ftz) — Canada - [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 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