---
title: 'Talent Acquisition Partner (Contract) at Tailscale'
canonical: 'https://feeny.ai/job/talent-acquisition-partner-contract-tailscale-canada-v41jpdhh47hk'
type: 'job'
last_seen: '2026-09-08'
---

# Talent Acquisition Partner (Contract) at Tailscale

- **Company:** Tailscale
- **Location:** Canada
- **Compensation:** $90–$109/hr
- **Work type:** remote
- **Posted:** 2026-09-03
- **Last confirmed live:** 2026-09-08
- **Apply:** https://job-boards.greenhouse.io/tailscale/jobs/4728969005

## 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 hiring multiple experienced Talent Acquisition Partners to join Tailscale on an initial 6-month contract basis, with the potential to extend and/or convert to full-time roles based on business needs and performance.

These roles will support different parts of the organization, with individual assignments focused on Engineering, Product & Design (EPD), Go-to-Market & G&A, or a broader cross-functional portfolio spanning multiple organizations. During the application process, candidates will have the opportunity to indicate where they have the most experience and where they would prefer to focus.

You’ll operate as a fully integrated member of our Talent Acquisition team, owning searches from intake through offer and partnering with hiring managers and business leaders to develop thoughtful recruiting strategies, navigate competitive talent markets, and deliver an exceptional candidate experience.

Tailscale operates in a highly technical, fast-moving environment, so we’re looking for recruiters who are curious, adaptable, and comfortable learning new areas quickly. Whether your background is primarily technical, commercial/corporate, or broad-based, you’ll bring strong recruiting craft, market intelligence, data, and sound judgment to help hiring teams make great decisions while maintaining a consistently high hiring bar.

## Key Responsibilities

Lead Full-Cycle Recruiting

- Own complex searches from intake through offer across EPD, GTM, G&A, or a combination of functions based on assigned business needs.
- Partner with hiring managers to define candidate profiles, develop recruiting strategies, and establish effective interview processes.
- Manage multiple searches while maintaining a high bar for quality, speed, and candidate experience.
- Lead candidate assessment, offer strategy, negotiation, and closing in partnership with hiring teams.

Develop Talent & Sourcing Strategies

- Build recruiting and sourcing strategies based on business priorities, role requirements, talent availability, and market conditions.
- Partner with Sourcers on targeted searches and talent mapping while sourcing directly as needed and maintaining accountability for pipeline health.
- Use recruiting data, candidate feedback, and market intelligence to evaluate search performance and adjust strategies.
- Identify alternative talent pools, companies, locations, or profiles when searches require a different approach.

Advise & Influence Hiring Teams

- Build trusted relationships with hiring managers and business leaders and serve as a consultative recruiting partner.
- Provide actionable insights on talent markets, candidate expectations, hiring timelines, and potential tradeoffs.
- Constructively challenge assumptions and create accountability around interview quality, timely feedback, decision-making, and candidate experience.
- Proactively identify hiring risks and partner with TA leadership when broader support or escalation is needed.

Recruit Across Your Area of Focus

Depending on your background and assignment, you may support:

- Engineering, Product & Design: including highly technical or specialized Engineering, Product, Design, and leadership searches.
- GTM & G&A: including Sales, Customer Success, Marketing, Revenue Operations, Partnerships, Finance, Legal, People, and other business functions.
- Cross-Functional / All Orgs: a mix of technical and non-technical hiring across the company as priorities evolve.

Partner Across Talent Acquisition

- Collaborate closely with Sourcers, Coordinators, TA Operations, fellow TA Partners, and TA leadership.
- Share market insights, sourcing approaches, and recruiting best practices across the team.
- Contribute to recruiting initiatives and process improvements that strengthen hiring effectiveness and scalability.

## What We Are Looking For

- 6+ years of full-cycle recruiting experience, ideally within high-growth SaaS, cloud, infrastructure, developer tools, cybersecurity, or other technology environments.
- Demonstrated success recruiting within EPD, GTM/G&A, or across multiple functions and levels.
- Strong full-cycle recruiting skills across intake, sourcing, candidate assessment, stakeholder management, offer negotiation, and closing.
- Experience developing recruiting and sourcing strategies for complex or highly competitive searches.
- Ability to quickly understand unfamiliar technical or business roles and translate hiring needs into effective recruiting strategies.
- Proven ability to partner with hiring managers and business leaders as a trusted advisor, using strong judgment to influence decisions, challenge assumptions, and maintain accountability.
- Comfort using recruiting data and market intelligence to diagnose challenges and improve hiring outcomes.
- Excellent communication, organization, and prioritization skills with the ability to independently manage multiple searches in a fast-moving, distributed environment.

## Nice to Have

- Experience recruiting across multiple areas of the business, including both technical and non-technical functions.
- Experience recruiting highly technical talent within infrastructure, networking, security, distributed systems, developer tools, cloud, or adjacent areas.
- Experience recruiting Sales and broader GTM talent across different functions, levels, or sales motions.
- Experience partnering with Sourcers on sophisticated strategies for difficult-to-fill roles.
- Experience using talent mapping, market intelligence, recruiting data, AI, or emerging recruiting technologies to improve hiring outcomes.

Note: this is a contract position and is not eligible for the full-time, exempt benefits listed below. CAN Pay Range $90—$109 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)

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