T

Tailscale

Connects devices through encrypted private networks

Solutions Engineer - Commercial, Expansion Sales

Full-Time
CA$201k - CA$268k+ Equity incentive plan + Variable commission + Employer retirement match
Mid, Senior
Remote in Canada
Remote
Solution EngineeringPre-Sales Solution Engineering

About the job

Requirements
  • At least 4–5 years of experience in a customer-facing solutions engineering or solutions architecture role within networking or security software.
  • Proven experience co-owning pipeline and influencing quota outcomes with Sales.
  • Strong networking fundamentals, including TCP/IP, DNS, routing, firewalls, and troubleshooting.
  • Deep understanding of zero-trust networking, secure connectivity, and identity and access management integrations, including SSO, SAML, and OIDC.
  • Understanding of AI gateway and governance platforms for centralized large language model access, usage visibility, and audit.
  • Familiarity with privileged access management, including session recording, just-in-time access, and protocol-aware controls; examples include Border0, CyberArk, and Teleport.
  • Experience with infrastructure-as-code tools such as Terraform, Pulumi, Ansible, or CloudFormation.
  • Hands-on architecture experience with AWS, GCP, and/or Azure.
  • Strong communication skills and the ability to translate technical features into business value.
  • Experience thriving in high-growth or startup environments.
Responsibilities
  • Partner with Account Executives to identify, qualify, and close new Commercial customer opportunities.
  • Lead technical discovery, solution architecture, demos, and proofs of concept to accelerate decision-making.
  • Guide complex multi-stakeholder deals, aligning technical and business objectives.
  • Provide structured feedback to shape the product roadmap and go-to-market strategy.
  • Build scalable enablement resources, demo environments, and solution blueprints for the solutions engineering team.

About the company

Tailscale connects people, servers, and applications through encrypted private networks, giving businesses and individuals access to resources across clouds and physical locations. Its software uses WireGuard to encrypt traffic and connects devices directly where network conditions allow, with encrypted relay paths for harder connections. Administrators use identity services and access policies to manage who reaches each resource, without exposing every system to the public internet. The company sells business subscriptions priced by seats, with additional controls for larger teams and a free plan for personal use. Founded in 2019, Tailscale is headquartered in Toronto, Ontario, Canada.

Company Size

201-500

Company Stage

Series C

Total Funding

$275M

Headquarters

Toronto, Canada

Founded

2019

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Simplify Jobs

Simplify's Take

What believers are saying

  • Business adoption creates distribution: Tailscale reports 40,000 businesses using its platform.
  • Employee rewards extend beyond salary: Tailscale lists equity incentives, employer-funded retirement contributions, and ongoing professional development.
  • Customers embed several features: Instacart uses Tailscale for HIPAA-restricted access, split DNS, and third-party IP allowlisting.

What critics are saying

  • Sales roles limit location freedom: Tailscale says some sales teams work in an office a few days weekly.
  • Relay paths constrain performance: Tailscale's documentation says encrypted relay connections are generally slower than direct links.
  • Privilege controls failed: July 2026 disclosure described a patched Linux SSH flaw permitting root access despite user restrictions.

What makes Tailscale unique

  • Customers control device admission: Tailnet Lock requires trusted customer devices to cryptographically sign new devices' keys.
  • Core networking is inspectable: Tailscale publishes its client daemon, command-line tools, and relay server code as open source.
  • Local services reach outside users: Tailscale Funnel publishes a device's service through HTTPS without requiring visitors to install Tailscale.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Flexible Work Hours
  • Remote Work Options
  • Unlimited Paid Time Off
  • Parental Leave
  • Professional Development Budget
  • Home Office Stipend
  • Phone/Internet Stipend
  • Company Equity

Growth & Insights and Company News

6 month growth

0%

1 year growth

1%

2 year growth

1%
SecurityWeek
Oct 27th, 2026
Tailscale rushes patches after uncoordinated disclosure of 'Tailworm' flaws.

Tailscale rushes patches after uncoordinated disclosure of 'Tailworm' flaws. Tailscale is preparing a patch for Tailscale SSH flaws whose details went public over the weekend, before any fixes had been released. | October 27, 2026 (11:26 AM ET) Tailscale is getting ready to ship a client update that addresses privilege escalation weaknesses in Tailscale SSH. Details of the bugs went public over the weekend. Tailscale provides a mesh VPN service that uses the WireGuard protocol to connect an organization's devices and services over a private, peer-to-peer network. The Tailscale vulnerabilities, dubbed Tailworm, are described in a report from Cyberdione Labs. It lists 11 findings affecting version 1.104.2 of the Tailscale client and version 0.29.5 of headscale, an open source control server that organizations can host themselves. Cyberdione Labs published the report before any patches were available, drawing criticism on social media, though the researchers argued that rapid awareness would speed up remediation. Six of the findings are rated high severity, and four of them concern Tailscale SSH, which grants access based on device identity and network policy instead of passwords or keys. According to the Tailworm report, Tailscale SSH performs some forwarding operations with root privileges, and the safeguards meant to restrict them can be bypassed. An attacker who has compromised one device could exploit this against any server that device is permitted to reach over Tailscale SSH, as long as the access rule allows forwarding. In lab tests, this resulted in root access on target servers and the theft of keys that can be used to add rogue devices to the network. That initial foothold could come from common methods such as phishing, a vulnerable web application or a malicious software package. Researchers showed that these SSH flaws are wormable. Since no user credentials are involved, an automated attack chaining these bugs moved from machine to machine across every server the policy granted SSH access to, at under a second per hop and with no user interaction. The report also describes flaws in an experimental app connector feature, the Serve feature, headscale and the client's relay component that could be exploited to reach cloud metadata services and internal networks while bypassing access rules, expose a node's administrative interface to remote peers, or cause denial-of-service (DoS) conditions. Tailscale says fixes are close. Responding on Reddit, Tailscale VP of Engineering Mike Shaver said the company was already running its own investigation, with input from outside security specialists, when the report came in. "Most of the issues we've identified so far concern what happens after someone has been authorized to connect, particularly how Unix privileges and SSH forwarding are handled. In some cases, a session may be able to do more than the configured local user should be allowed to do," Shaver said. "While it's a serious concern, it isn't the same as an unauthenticated attacker being able to connect to arbitrary machines, but the potential impact depends on how SSH access is configured," he added. In an update shared on Monday, Tailscale said fixes were in place for most of the issues and that it was aiming to release a patched client by the end of Tuesday, October 27, pending testing. A security advisory and a technical write-up will follow once the update is out. The Tailworm report, updated on Tuesday, says fixes for several findings have landed in Tailscale's public code repositories. None had made it into a numbered release at that point. "Based on our current assessment, we're not recommending that everyone disable Tailscale SSH," the vendor said. Until the patch arrives, Tailscale advises organizations to review their SSH access policies and disable SSH forwarding where it isn't needed, which it says mitigates several of the more serious findings. Neither Tailscale nor the Tailworm report mentions in-the-wild exploitation. Eduard Kovacs (@EduardKovacs) is senior managing editor at SecurityWeek. He worked as a high school IT teacher before starting a career in journalism in 2011. Eduard holds a bachelor's degree in industrial informatics and a master's degree in computer techniques applied in electrical engineering.

Daily AI Tools
Oct 27th, 2026
Tailscale warns of SSH flaws allowing root privilege escalation.

Tailscale warns of SSH flaws allowing root privilege escalation. By Sergiu Gatlan Tuesday, October 27, 2026 BleepingComputer Tailscale has disclosed 11 vulnerabilities in its SSH implementation that could allow attackers to escalate privileges to root, crash nodes, or hijack sessions. Because Tailscale bridges private networks, these flaws are particularly dangerous, potentially turning a single compromised client into a gateway for lateral BleepingComputer

PR Newswire
Oct 13th, 2026
Speakeasy and Tailscale partner to bring private networking to enterprise MCP gateways

Speakeasy, an AI control plane for enterprise, has partnered with Tailscale to bring private networking to enterprise Model Context Protocol (MCP). Companies can now run Speakeasy's MCP gateway as a node on their own Tailscale network, known as a tailnet. Many MCP deployments still rely on publicly reachable endpoints. With the integration, the public route can be closed, and every request carries the Tailscale user and device identity it came from. Speakeasy adds MCP-specific governance and policy on top of Tailscale's private connectivity. Payments company Polar uses it to keep its internal MCP servers off the public internet. The feature is available now for Enterprise organizations and is rolling out per organization. Tailscale is the first supported private network provider.

The IT Infrastructure Report
Aug 31st, 2026
Tailscale expands from VPN into full connectivity platform.

Tailscale expands from VPN into full connectivity platform. Application Infrastructure August 31, 2026 Highlights. * Tailscale is expanding beyond its original VPN product with new services introduced at its Tailscale Up conference. * The new offerings include DNS Filtering by Control D, Tailscale PAM, Aperture, Aperture Plus, Tailcat, and developer APIs and SDKs. * Tailscale said its identity-based access model now supports services for DNS control, privileged access, AI agents, and software development. Tailscale, which began in 2019 as a VPN provider based on open-source WireGuard technology, is moving beyond its original VPN pitch with a series of new products. The company raised $160 million last year to expand its WireGuard-based VPN platform and used its Tailscale Up conference last week to introduce new services built on identity-based access. Tailscale ties access to a device or user identity rather than to an IP address and applies policy based on that identity to determine what can be reached. The company said that model now underpins a broader set of tools, including DNS Filtering by Control D, Tailscale PAM, Aperture, Aperture Plus, Tailcat, and developer APIs and SDKs. DNS Filtering by Control D is sold and managed through existing Tailscale policy to block malicious and unapproved destinations. Tailscale PAM, now in beta, adds credential injection and just-in-time access for sensitive infrastructure. The company said it acquired Border0 in March 2026, and that Tailscale PAM lets teams grant one-click access to servers, databases, Kubernetes clusters, and web applications without handing out standing passwords or API keys. Aperture is Tailscale's AI gateway and reached general availability at the event. It gives AI agents an identity on a tailnet and routes their model calls and tool use through Tailscale's private network rather than the open internet. Aperture Plus extends the same access model into a browser, works without installing Tailscale as a system-level VPN, and isolates each session. Tailscale also introduced SDKs for Rust, Python, C, C++ and Elixir, along with a Tailnet Creation API and declarative tailnet sharing. company spotlight SoftIron. SoftIron makes the products that underpin the next evolution of IT infrastructure. Its blueprint is radical. Taking full control over design and manufacture of platforms optimised to transform IT infrastructure, its highly integrated products reduce space and energy footprints while delivering extraordinary performance. Challenging traditional IT manufacturing & organisational strategy, IT Infrastructure has developed a model that enables IT Infrastructure to create a more resilient and connected business for the customers IT Infrastructure serve. A commitment to openness, transparency, and simplicity helps address emerging multi-faceted threats while eliminating the vendor "lock-in" so common elsewhere.

Control D
Aug 28th, 2026
Control D is now available through Tailscale.

Control D is now available through Tailscale. Buy Control D directly through Tailscale and filter every device on your tailnet, with different policies by user, group, or tag. Control D can now be purchased directly through Tailscale. Point your tailnet at Control D and every device on it is filtered, with different policies for users, groups, and tags. Teams have been running Control D natively on their tailnets for some years now. While Tailscale connects your devices into a private network and controls what they can reach inside it, Control D handles the other half, providing controls and filters for access to the public internet. Running both meant managing two separate vendors and invoices. Today ControlD Inc is proud to make it official and partner with Tailscale. You can now buy Control D directly through them, and run it across every device on your tailnet from a single vendor. How the partnership works. In Control D, a Profile is the set of rules you want enforced, and an Endpoint is a resolver that enforces one. Every Endpoint has a Resolver ID. Add Control D as a nameserver in the Tailscale admin console, paste the resolver ID in, switch on Override DNS servers, and every device on your tailnet resolves through it, with nothing to install and no network changes. Its docs cover the details. What's new is the commercial side. Tailscale's team handles your day-to-day support, and ours behind them on anything deeper. Policy management stays where it is, in your Control D Dashboard and API. What Control D adds to your tailnet. Threats stopped at the resolver. Control D checks every query against curated threat feeds, then against the domains and IPs those campaigns are built on, so infrastructure caught once stays caught when it resurfaces under a new name. Unknown domains are scored by machine learning and blocked if they look high risk. Control D has consistently ranked first in independent malware filter tests, most recently with a 99.98% block rate. Beyond malware and phishing, 20+ native content categories and over 1,000 services and apps can each be allowed, blocked, or redirected individually for granular policy control. Policies that follow your tailnet. Different parts of your tailnet can enforce different rules. In your tailnet policy file, nodeAttrs maps users, groups, or tags to a Control D Endpoint, so filtering inherits the structure you already built for network access. Tag a machine and its policy follows, without enrolling each device in Control D separately. Where a device inherits more than one tag, priority values decide which one wins. This shares only device hostnames with Control D, and you control how much query data is kept. More than one tailnet. Plenty of teams run several, whether that is production and staging, one per subsidiary, one per department/team, or one per client if you are an MSP. Organizations and Sub-Organizations give each its own policy scope, Shared Profiles push a common baseline across all of them, and delegated administration lets whoever runs one manage it without touching the others. Getting started. Already using Tailscale? Talk to the Tailscale sales team about adding Control D to your plan.