Thank you for considering Tailscale. If this job description resonates with you, please apply. 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!
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.
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 ResponsibilitiesLead 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.
- 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.
- 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.
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.
- 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.
- 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.
- 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.
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.
Similar Jobs
.png)
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
