Manager, Commercial Expansion

Tailscale; Toronto; Hybrid; CAD 268,000 - 335,000; Full time

Benefits offered by this job

Remote-first environment

Competitive compensation includingbase

Equity incentive plan

Comprehensive benefits

Job summary

Tailscale is seeking a gritty, thoughtful Sales Manager to lead an Expansion team in Toronto. You will guide an account executives group, drive pipeline, and close mid-to-large opportunities in the Commercial segment.

Based in Toronto with hybrid work (3 days in-office), you will build a scalable sales machine from the ground up, partnering with marketing, product, and partnerships to accelerate growth across Canada and beyond.

Qualifications

• 1+ years of sales management experience in a B2B SaaS/Software company.
• Aptitude for delivering world-class customer experiences and adding value in interactions.
• Excellent written and verbal communication skills.
• Ability to travel to industry events once a quarter.
• This role is based in Toronto and is hybrid (3 days/week in-office).

Responsibilities

• Lead a team of account executives from the front—prospecting with the team and guiding opportunities.
• Unblock critical deals and travel to customers to build relationships.
• Establish and refine best practices for pipeline generation and opportunity management.
• Develop and coach the team using sales data, performance metrics, and enablement.
• Collaborate with marketing, product, sales engineering, and partnerships to accelerate opportunities.

Skills

Sales leadership

B2B SaaS

Communication

Team coaching

Strategic account planning

Education

Bachelor's degree

Tools

Salesforce

Job description

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.

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.

About The Role

We are looking for a gritty, thoughtful, and curious Sales Manager to lead an Expansion (existing customers) sales team focused on the Commercial segment (<750 employees). The Commercial team balances both a high velocity sales motion (7 to 13 opportunities per month) and occasional large opportunities ($50,000-$100,000+ ACV contracts). You will be the first sales leader to build out our new Toronto sales hub. If you are looking for an opportunity to lead from the front and to build a repeatable sales machine from the ground up, this is it.

Key Responsibilities

• Become an expert in how Tailscale helps our customers
• Lead a team of account executives from the front - prospecting with the team, leading role plays, unblocking critical opportunities, and traveling to customers to build relationships
• Establish and refine best practices for pipeline generation, opportunity management, and customer relationship building
• Develop and coach the team using sales data, performance metrics, and sales enablement
• Work closely with marketing, product, sales engineering, and partnership teams to create pipeline and accelerate opportunities

What We Are Looking For

• 1+ years of sales management experience in a B2B SaaS/Software company
• Aptitude for delivering world-class customer experiences: operate with a sense of urgency, exercise curiosity about customers, and strive to add value in your interactions
• Excellent written and verbal communication skills
• Ability to manage many activities and tasks simultaneously
• Ability to travel to industry events once a quarter
• This role is based in Toronto and is hybrid required (3 days/week in-office).

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

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.
• 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.