Engineering Manager

Tailscale; United States; Remote; CAD 272,000 - 344,000; Full time

Benefits offered by this job

Base salary and equity package

Group health benefits

Remote-first culture

Employer-funded retirement plan

Company retreats and team off-sites

Job summary

Tailscale, a fully remote software company, is seeking a Software Engineering Manager to guide multiple Pods of engineers. You will mentor teams, drive technical direction, and help recruit as the company grows.

You’ll lead efforts across engineering, product, and design to deliver high-availability services. We value strong leadership, experience with Go, and the ability to operate in a fast-paced startup environment.

Qualifications

• Proven leadership with mentoring and performance evaluations.
• Experience building and operating production services with high availability.
• Expertise managing on-call rotations and incident response.
• Strong technical judgment in design discussions, with ability to leverage team expertise.
• Experience developing in Go, used for substantial parts of the system.

Responsibilities

• Provide guidance, mentorship, and career development for engineers.
• Lead Pods (2–4 engineers + PM + Designer) and oversee 2–3 Pods.
• Provide technical direction on projects and grow engineering leadership.
• Assist in interviewing, recruiting, and shaping engineering culture/processes.
• Oversee a critical production service, including monitoring and on-call responsibilities.
• Moderate design discussions to maintain a positive feedback culture.
• Collaborate across disciplines to complete multi-domain projects.
• Drive planning from immediate needs to long-term strategy.

Skills

Leadership

People management

Incident response

Go programming

Independent work

Startup environment

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 seeking a talented and motivated full-time Software Engineering Manager to join our growing team. You will work as part of the engineering team to:

• Provide guidance, mentorship, and career development for a team of software engineers.
• Contribute toward the success of our Product organization which includes Engineering, Product Management, and Design. We operate in Pods of 2-4 engineers plus a Product Manager and Designer, and each Engineering Manager handles 2-3 such Pods.
  Pods work across the codebase to implement features, address shortcomings, and answer customer requests.
• Provide technical direction in projects as needed, as well as growing the technical leadership capabilities of the engineers reporting to you.
• Help in growing the organization: interviewing and recruiting, guiding the development of the engineering culture, developing processes as we grow.

Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.

Key Responsibilities

• Experience as a people manager: we are not yet at a size and level of maturity as an engineering org to provide the training and support for someone new in the management role.
• Achieve significant business outcomes through cross-functional collaboration with product managers, data scientists, and designers
• Help your team to improve their performance, the quality of their work; make major design decisions
• Hire, nurture, and oversee a team of engineers while fostering an atmosphere of psychological well-being, embracing diversity and promoting inclusion.
• Lead a team responsible for managing a critical production service, including operational concerns (monitoring, alerting, on call, etc)
• Manage healthy conflict by moderating design discussions and cultivating a positive culture of feedback with candor and kindness
• Collaborate with interdisciplinary teams across the organization to complete complex projects spanning multiple technical domains
• Drive planning across multiple time horizons, from immediate tactical needs to long-term strategic direction.

What We Are Looking For

• Demonstrated leadership with substantial experience in managing and mentoring Engineering teams, including performance evaluations, career development, and fostering a collaborative work environment
• Background building and operating production services with high availability and performance targets.
• Expertise managing on call rotations and incident response
• A highly technical manager, able to independently evaluate complex technical tradeoffs in design conversations while leaning on experts in the team for design and implementation
• Experience developing in Go, used for much of the system
• Ability to give and process constructive feedback, as well as work independently
• Flexibility to adjust to the dynamic nature of a startup

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

$272,040 - $344,380 CAD

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 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 .