Thank you for considering Tailscale. If this job description resonates with you, please apply. 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!
About the RoleWe're looking for a thoughtful, curious, and driven Sales Manager to lead a team of Commercial Account Executives focused on growing existing customer relationships. You'll coach and develop reps, own team performance, and help them navigate both fast-moving expansion opportunities and larger, more complex deals.
As our first sales leader in Vancouver, you'll help establish our new sales hub, hire and develop talent, and build a repeatable expansion sales motion. This is a hands-on opportunity to shape a growing team and help more customers realize the value of Tailscale.
Key Responsibilities- Help establish Tailscale's new sales hub, hire and onboard Commercial Expansion AEs, and create a culture of curiosity, accountability, and shared success
- Drive expansion revenue, maintain a healthy pipeline, and deliver accurate forecasts
- Prospect alongside reps, join customer conversations, and help navigate pivotal deals - from fast-moving expansions to larger, more complex opportunities
- Turn call reviews, role plays, and deal strategy sessions into practical coaching that sharpens skills and supports career growth
- Build and refine a repeatable expansion playbook, using sales data and customer insights to test approaches and scale what works
- Develop a deep understanding of Tailscale's value and partner with Customer Success, Marketing, Product, Sales Engineering, and Partnerships to grow adoption
What We Are Looking For- At least 1 year of people management experience in a B2B SaaS sales environment
- Proven ability to coach, develop, and motivate Account Executives or other quota-carrying sales professionals
- Strong understanding of the sales process, including prospecting, discovery, qualification, pipeline management, and closing
- Experience driving team performance through data-driven decision-making, structured coaching, and clear accountability
- Ability to thrive in a fast-paced, high-velocity sales environment while managing multiple priorities
- Excellent written and verbal communication skills, with the ability to engage both technical and nontechnical stakeholders
- A curious, proactive mindset with a bias for action and a passion for continuous improvement
- Willingness to travel approximately once per quarter
- Ability to work from our Vancouver office three days per week
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)
$268,000-$335,000 CAD
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.
- Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
- 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 $500 USD to customize your workstation to make it your own.
- Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).
