Solutions Engineer, Tailscale
Commercial, Expansion Sales
CA$201-268k
OTE
+ Equity
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
201-500 employees
Be an early applicant
CA$201-268k
OTE
+ Equity
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 4/5+ years in a customer-facing SE/SA role within networking or security software
- Proven experience co-owning pipeline and influencing quota outcomes with Sales
- Deep understanding of zero-trust networking, secure connectivity, and IAM integrations (SSO, SAML, OIDC)
- Hands-on architecture experience with AWS, GCP, and/or Azure
- Strong networking fundamentals (TCP/IP, DNS, routing, firewalls) and troubleshooting skills
- Excellent communication skills, capable of translating technical features into business value
- Experience thriving in high-growth or startup environments
- 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 the job involves
- Tailscale is seeking an experienced Commercial Solutions Engineer to partner with Sales in driving new business for Commercial customers
- You will co-own a book of business with Account Executives, lead technical discovery and architecture design, and act as a trusted advisor to customers
- This role blends deep networking and security expertise with strong sales acumen to win competitive deals, scale enablement, and influence product direction
- Partner with AEs to identify, qualify, and close new Commercial customer opportunities
- Lead technical discovery, solution architecture, demos, and POCs to accelerate decision-making
- Guide complex multi-stakeholder deals, aligning technical and business objectives
- Provide structured feedback to shape product roadmap and GTM strategy
- Build scalable enablement resources, demo environments, and solution blueprints for the SE team
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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