Manager of Solutions Engineering, Tailscale
Enterprise
CA$335-368.5k
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$335-368.5k
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
- Experience leading people, ideally as a working manager who still enjoys being in the details
- Experience in a technical, enterprise customer-facing role such as Solutions Engineer, Sales Engineer, or similar
- Clear, confident, opinionated communication skills—you can explain complex systems simply, read the room, and land a point without over-explaining
- Solid understanding of networking and security fundamentals, including cloud environments such as AWS VPCs and Azure virtual networks
- Hands-on technical background with experience in developer tooling, DevOps principles, and modern cloud architectures (CI/CD, infrastructure, APIs)
- Ability to explain Tailscale’s value in your own words, grounded in customer outcomes and technical trade-offs rather than marketing language
- This role is not a good fit if you are looking to move away from being technical, prefer managing through frameworks instead of real deal work, default to generic playbooks, or optimize primarily for future scale over present-day impact. We’re looking for judgment, energy, and credibility - not a perfectly adequate manager
- 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
- We are looking for a Manager, Solutions Engineering – Enterprise & Mid-Market to join our rapidly growing team
- The Solutions Engineering team partners with customers across the full lifecycle - from pre-sales through post-sales - by helping design, evaluate, and operationalize Tailscale in complex enterprise environments
- This role exists to raise the quality of enterprise execution: better discovery, tighter technical evaluations, and clearer articulation of why Tailscale actually matters in a real-world architecture
- The team works closely with Sales, Support, and Product, and collaborates deeply with Engineering and Marketing so customer feedback doesn’t disappear into a backlog
- As Manager of Solutions Engineering, you will act as a true player-coach: showing up on important deals, coaching experienced SEs in real moments, and setting a high bar for how enterprise engagements should be run
- If you care about people leadership, enjoy being close to the technology, and want to stay customer-facing while building a high-performing team of smart, self-sufficient solutions engineers, we should talk
- Manage and grow a small, senior team by coaching on live deals, developing judgment and technical depth, and hiring people who make the team better - not just bigger
- Set and uphold a high standard for enterprise discovery, technical evaluations, and successful rollouts that directly impact new customer acquisition and expansion
- Partner closely with Sales as a credible technical counterpart on complex enterprise opportunities, helping shape deal strategy, architecture, and execution quality
- Collaborate across Tailscale to improve how we run proofs of concept, explain technical value, and turn real customer feedback into product direction
- Provide clear, actionable feedback to Product and Engineering grounded in concrete customer use cases and enterprise constraints (not hypotheticals)
- Stay current on cloud, DevOps, networking, and security trends, and help the team continue sharpening both technical instincts and communication skills
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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