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.

We’re looking for an experienced Talent Acquisition Operations professional to help build and scale the operational foundation of Tailscale’s Talent Acquisition organization. You’ll partner closely with TA leadership, Talent Acquisition Partners, Sourcers, Coordinators, and cross-functional teams to build efficient, scalable recruiting processes and deliver an exceptional candidate and hiring team experience. You’ll own and improve core areas including recruiting systems, analytics and reporting, process design, coordinator operations, and operational programs.

We’re looking for someone who enjoys solving operational problems, creating structure, and using technology and data to make recruiting more effective. You’ll have the opportunity to expand your ownership over time and help shape how Talent Acquisition Operations evolves as Tailscale scales.

Talent Acquisition

Operations & Systems Administer, configure, and continuously optimize our recruiting technology stack, workflows, permissions, integrations, templates, and operational processes. Partner with TA leadership to identify and implement process and system improvements across the recruiting lifecycle. Support recruiting technology implementations, upgrades, integrations, and vendor relationships.

Talent Acquisition

Analytics & Reporting Build and maintain recruiting dashboards and recurring reporting that provide visibility into hiring progress, pipeline health, funnel performance, recruiting activity, and other key metrics. Analyze recruiting data to identify trends, bottlenecks, risks, and opportunities, translating findings into actionable insights for TA and business stakeholders. Partner with TA leadership to define meaningful recruiting metrics and reporting cadences that support team performance and business decision-making.

Support headcount tracking, hiring forecasts, and data quality to ensure reporting is accurate, consistent, and actionable.

Talent Acquisition

Programs & Process Improvement Design and implement scalable recruiting programs, processes, and operational initiatives that improve team effectiveness and candidate experience. Create and maintain recruiting playbooks, hiring guides, process documentation, and other resources that drive consistency and adoption. Lead operational projects from planning through implementation in partnership with People, Finance, IT, Legal, and other cross-functional teams.

Talent Acquisition Coordinator Partnership





Partner closely with Talent Acquisition Coordinators to improve scheduling operations, candidate communications, interview logistics, and candidate experience. Serve as an operational resource and escalation point for complex coordination or recruiting process challenges. Document and optimize coordinator workflows, identify opportunities for automation and process improvement, and help build scalable operating practices.

Recruiting

Technology, Automation & AI Partner with the Talent Intelligence, Sourcing & AI Programs Lead to operationalize recruiting technologies, AI-enabled workflows, and automation initiatives. Support implementation, documentation, enablement, and adoption of new tools and workflows across Talent Acquisition. Identify opportunities to reduce manual work, improve data quality, and create more efficient recruiting experiences through technology and automation.

Ensure new tools and workflows integrate effectively with existing recruiting processes while maintaining appropriate standards for data quality, privacy, and candidate experience. Maintain recruiting documentation, operational standards, and processes that support compliance and audit readiness. Partner with appropriate stakeholders to ensure recruiting processes align with internal policies and applicable employment requirements.

Identify and address operational risks while continuously improving the consistency, effectiveness, and scalability of recruiting operations. 3+ years of experience in Talent Acquisition Operations, recruiting coordination, Talent Acquisition, People Operations, or a related operational role, ideally within a high-growth environment. Hands-on experience administering and improving Applicant Tracking Systems and recruiting technologies such as Greenhouse, ModernLoop, or similar platforms. Strong operational and project management skills, with experience designing processes, improving workflows, and creating scalable documentation.

Strong analytical skills and comfort building reports, working with recruiting metrics, and translating data into actionable insights. Strong attention to detail and judgment, with the ability to maintain data integrity while managing multiple priorities and operational initiatives. Excellent communication and cross-functional partnership skills, with the ability to work effectively across Talent Acquisition, People, Finance, IT, Legal, and business teams.

A continuous improvement mindset and comfort navigating ambiguity, adopting new technologies,



and building scalable solutions as the organization evolves.

Experience supporting Talent Acquisition Operations within a high-growth or globally distributed technology company.

Experience with recruiting technologies such as Greenhouse, ModernLoop, Crosschq, Metaview, LinkedIn Recruiter, or similar platforms.

Experience building recruiting dashboards and reporting using Google Sheets, Looker, Tableau, or similar analytics tools.

Experience using automation or AI-enabled tools to improve recruiting workflows, data quality, or operational efficiency.

Experience supporting Talent Acquisition Coordinators and building scalable coordination practices.

Experience leading recruiting programs, systems implementations, or cross-functional operational initiatives. Tailscale's compensation package includes base salary, equity, and comprehensive advantages. The salary range displayed on each job posting represents the target range for a new hire's base salary. 134,000 — $174,200 CAD We encourage you to help us break that statistic!

An inclusive, flexible environment where you can be your authentic self. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles). 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 .

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. 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. 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. 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).

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.

📌 Senior Talent Acquisition Operations Partner (Winnipeg)
🏢 Tailscale
📍 Winnipeg