Tailscale

Engineering Manager, Strategic Projects

Remote (Canada) · Exec · Full-time

Sponsorship not specified$10k-$15kDetected 5 days ago

Platform EngineeringOAuthLLMsAgentic AIStatisticsCadenceDNSCollaborationMentoring

About the role

From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more.
Job Description We're seeking a full-time Software Engineering Manager for our Strategic Projects team.
Aperture, our identity-aware LLM gateway, is one such initiative.

Manage a talented, senior team of experienced engineers in a growth-stage startup.
Drive business outcomes measured by adoption of new platform primitives, customer integrations landed, and influence on Tailscale's roadmap.
Make major design decisions on prototypes that often graduate into production surface area, and own the quality bar for the team's externally-visible artifacts (reference architectures, open source, talks, customer integrations).
Collaborate across core platform engineering, security, and go-to-market on projects that span domains and often involve direct customer co-development.
Drive planning across horizons, balancing fast prototype cycles against longer-arc bets on where connectivity, identity, and AI infrastructure are converging.
Experience developing in Go, the primary language across Tailscale's stack and this team's prototypes
Comfort with exploratory, customer-facing engineering: translating customer conversations into prototypes and reference designs
We support intentional in-person connection through team travel and distributed collaboration.
Support for your personal and professional development.

Light travel required (~10-15%): primarily team and company onsites, with occasional conferences or customer visits concentrated in North America with potential trips to EU or APAC.

Networking background (L4-L7 connectivity, browser and DNS behaviors), and familiarity with Tailscale itself
Identity infrastructure background: IdP platforms, identity sync/provisioning, directory services, and protocols (OAuth, OIDC, SAML, SCIM)
access control models (RBAC/ABAC), session management, MFA, passwordless auth
Leading teams whose output is publicly visible (open source, devrel, reference implementations) and validating prototype code for production alongside security teams
Individual offers may vary based on experience and skill set.
$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!

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.
Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.

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).
Comprehensive group benefits with no waiting period.
Take advantage of coverage for health, vision, dental, and more for you and your family!
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.
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).

If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

This listing is sourced directly from Tailscale's careers page and normalized into a canonical job model.