Manager, Commercial Expansion

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About TailscaleTailscale is making safe connection effortless 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.
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 Toronto, 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 Toronto 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.
CAN Pay Range$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).
Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Our hiring process uses AI‑assisted tools to help screen and assess candidates. All hiring decisions are made by people.
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