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Senior Revenue Operations Analyst

Remote (Canada)

About Tailscale 

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Job Description

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.

Key Responsibilities

  • 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

What We Are Looking For

  • 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.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

For this position, our pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

CAN Pay Range (OTE)

$160,800 - $201,000 CAD

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 We Offer

  • An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
  • A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
  • Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
  • Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
  • Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK. 
  • Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. 
  • Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! 
  • A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own. 
  • Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks. 

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.

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