Business Operations & Strategy

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

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.

Key Responsibilities

While projects can vary as the company evolves, below are a few examples of areas that the role could entail:

• 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.

What We Are Looking For

• 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

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.

CAN Pay Ranges

$134,000—$241,200 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 .