Senior Revenue Operations Analyst, Tailscale
CA$160.8-201k
OTE
Plus equity. OTE inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets
A zero config VPN for building secure networks
Job no longer available
A zero config VPN for building secure networks
201-500 employees
Job no longer available
CA$160.8-201k
OTE
Plus equity. OTE inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets
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
- 2+ years of operations experience in high-growth, startup organizations
- 1+ years of B2B SaaS experience with increasing responsibility and ownership
- Strategic thinker who can take broad visions and concepts and develop structured plans, actions, and measures and then execute those plans
- Experience in developing and executing sales planning (headcount, territories, compensation and incentive programs) that drive behavior
- Ability to operate in ambiguity and take broad, aspirational goals and turn them into scalable, repeatable processes, systems, and learning programs
- You are a clear, polished, OVER communicator: You can distill complex topics and ideas into something digestible from leadership to ICs
- Proven program management and project management skills
- Demonstrates ability to coach peers to up-level performance of the team
- Enjoy working in a high-growth, dynamic company environment, using the broader team within enablement platforms or learning management systems to convey value to customers
- Flexible and adaptable to meet the needs of the changing market, our customers, and our business
- Demonstrated ability to think strategically, and work in complex situations
- Naturally self-driven, results-oriented and able to work as part of a team
- You are passionate; you throw your energy and conviction into the work you do
- You are naturally curious; you have an innate desire to understand data, people and help problem solve for efficiency
- You are collaborative; you thrive in environments where people work together to create winning solutions
- You commit to self-development and personal growth; you pursue your personal and professional interests with energy and enthusiasm
- You assume positive intent; you believe your teammates and customers come from a place of good intention
What the job involves
- Tailscale is in need of an experienced Senior Revenue Operations Analyst to execute the strategy to drive operational rigor across the GTM team
- This role will work across departments to build systems and processes
- You will enable the Sales, Marketing, Partner, and Customer Experience teams to have consistent, effective, and engaging conversations with customers at each stage of the customer lifecycle while helping to improve the overall efficiency and effectiveness of our organization
- In this role, you will be challenged to develop the skills and experience to, over time, own a piece of the revenue Operations department
- Ensure all revenue-generating teams (sales, marketing, customer success) operate in harmony, with unified goals and seamless collaboration across the entire customer journey—from lead generation to onboarding and upselling
- Continuously evaluate and improve sales, marketing, and customer success workflows to remove bottlenecks, automate manual tasks, and streamline the customer experience for maximum efficiency and productivity
- Contribute meaningfully to the oversight of data quality across all revenue systems (CRM, marketing automation, customer data platforms), conduct regular audits, and implement governance to ensure reliable, actionable insights for decision-making
- Provide regular performance reports and insights to executives, enabling informed strategic decisions around forecasting and revenue generation
- Manage and streamline technology tools that support revenue operations, ensuring system integration, minimal manual work, and alignment with business needs
- Serve as the main point of contact between revenue teams, acting as tier 1 support for all questions and requests from sales and adjacent teams
- Monitor adherence to established processes and key performance indicators (KPIs), recommend adjustments to drive better adoption, and highlight IC performance trends to improve performance management
- Analyze data to uncover opportunities for revenue growth, lead projects to capitalize on these opportunities, and ensure the company is maximizing every revenue stream
- Document best practices, develop playbooks, and enable teams with the training and resources needed to scale repeatable, process-driven sales and marketing motions
- Collaborate with leadership to set KPIs, execute long-term strategies, and contribute to the creation of roadmaps for achieving company growth objectives
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.
Share this job
View 39 more jobs at Tailscale