FlexHired LogoFlexHired
Logo of Tailscale

Tailscale

Engineering Manager

Job Summary

This role is for a Software Engineering Manager at Tailscale, focusing on leading engineering teams, providing mentorship, and driving technical direction for the company's products. The candidate will manage cross-functional teams, oversee operational aspects of critical services, and foster a positive, inclusive work culture. Experience in managing engineering teams, developing in Go, and understanding networking protocols are preferred. The company offers a fully remote, flexible environment with comprehensive benefits and professional growth opportunities.

Required Skills

Technical Leadership
Networking
Cross-functional Collaboration
Mentoring
People Management
Conflict Resolution
Performance Evaluation
Go Programming
Recruiting
Operational Monitoring
BGP
Design Decision Making
L4-L7 Connectivity
Browser and DNS Behaviors

Benefits

Health Insurance
Paid Time Off
Parental Leave
Dental Insurance
Vision Insurance
Flexible Work Environment
Home Office Reimbursement
Equity
Company Retreats
Professional Development
Variable Compensation
Mentorship and Coaching

Job Description

About Tailscale

Tailscale is building the new Internet 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.

Job Description

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
  • 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

Nice to Have

  • Background in networking (including L4-L7 connectivity, browser and DNS behaviors, BGP and related protocols)

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 Ranges
$276,040$344,380 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.
  • Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK.
  • 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 $1000 USD to customize your workstation to make it your own.
  • Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

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.

Interested in this job?

Application deadline: Open until filled

Logo of Tailscale

Tailscale

Securely connect to anything on the internet with Tailscale. Deploy a WireGuard®-based VPN to achieve point-to-point connectivity that enforces least privilege.

See more jobs
Date PostedJune 25th, 2025
Job TypeFull Time
LocationRemote (Canada)
SalaryCompetitive rates
Exciting remote opportunity (requires residency in Canada) for a Engineering Manager at Tailscale. Offering competitive salary (full time). Explore more remote jobs on FlexHired!

Safe Remote Job Search Tips

Verify Employer Thoroughly

Research the company's identity thoroughly before applying. Check for a professional website with contacts, active social media, and LinkedIn profiles. Verify details across platforms and look for reviews on Glassdoor or Trustpilot to confirm legitimacy.

Never Pay to Get a Job

Legitimate employers never require payment for applications, training, background checks, or equipment. Always reject upfront payment requests or demands for bank details, even if they claim it's for purchasing necessary work gear on your behalf.

Safeguard Your Personal Information

Protect sensitive data like SSN, bank details, or ID copies. Share this only after accepting a formal, written job offer. Ensure it's submitted via a secure company system or portal, never through insecure channels like standard email attachments.

Scrutinize Communication & Interviews

Watch for communication red flags: poor grammar, generic emails (@gmail), vague details, or undue pressure. Be highly suspicious of interviews held only via text or chat apps; legitimate companies typically use video or phone calls.

Beware of Unrealistic Offers

If an offer's salary or benefits seem unrealistically high for the work involved, be cautious. Research standard pay for similar roles. Offers that appear 'too good to be true' are often scams designed to lure you into providing information or payment.

Insist on a Formal Contract

Always secure and review a formal, written job offer or employment contract before starting work or sharing final personal details. Ensure it clearly defines your role, compensation, key terms, and conditions to avoid misunderstandings or scams.

Related Jobs

Full Time
$190,280 - $237,180
Remote (Canada)
Full Time
Remote (Canada)
Full Time
Remote (Canada)
Full Time
Remote (Canada)
Full Time
Remote (Canada)

Subscribe Newsletter

Never miss a remote job opportunity. Subscribe to our newsletter today and receive exclusive job alerts, career advice, and industry insights delivered straight to your inbox.