Software Engineer, AI Enablement

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.

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.

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