Business Operations & Strategy, Tailscale
CA$134-241.2k
+ Equity and variable commission
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
101-200 employees
Be an early applicant
CA$134-241.2k
+ Equity and variable commission
101-200 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
- 2+ years of experience in Business or Strategy Operations at a high-growth tech company, consulting, investment banking, venture capital, private equity, etc
- Excellent business and technical acumen and analytical skills
- Ability to manage effectively with ambiguity and manage multiple projects and stakeholders to prioritize and re-prioritize in a rapidly changing environment
- Strong situational adaptability in both written and verbal communication
- Excellent communication and stakeholder management skills, capable of conveying complex concepts in simple terms
- Strong partnership skills within the Operations organization as well as with cross-functional teams
- Highly analytical and comfortable with SQL, spreadsheets, basic modeling, and presentation making
- (Bonus) You have experience with SaaS business models, GTM motion, or product-led growth
What the job involves
- We are looking for someone who wants to help scale a high growth startup and work cross-functionally across Sales, Marketing, Customer Experience, Operations, Product, and Engineering
- As companies scale quickly, needs and gaps can emerge, and we are looking for a high-functioning individual to help anticipate and solve challenges that may arise as we scale. You would take on a variety of projects helping to seed and structure areas of growth before projects grow to be undertaken by new people or teams. Personal humility and willingness to “give up your Legos” as the company grows will be a core part of the role
- As an early-stage and fully remote company, we are looking for motivated individuals who are comfortable working asynchronously, and thrive in ambiguity
- Work with leadership to develop goals consistent with our strategic vision and track progress
- Help design strategic board presentations and investor materials
- Assist with crafting executive communication around all hands, offsites, external parties, etc
- Help evaluate and reshape our pricing and packaging strategy. This may require gaining a deep understanding of new and existing product value, evaluating infrastructure costs, understanding and listening to customer feedback, and thinking about how to operationally simplify our business
- Reduce duplication in our business systems and set up processes to streamline and merge systems
- Help accelerate the use of AI tools at Tailscale
- Simplify our procurement process and look for efficiencies
- Help evaluate our international expansion strategy and help bring us into additional global markets. This can include examining our footprint globally and identifying regions that may be underserved and require more attention, as well as helping to coordinate efforts across functions to successfully expand into new markets
- Help design, implement, and improve business processes and internal systems (example could be improving billing for the partnerships team)
- Own end-to-end special projects, from scoping to execution and measurement
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 plan to develop its product further by tackling the complexity of software and confront operational problems that people face daily. The company continues its expansion by empowering 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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