Manager, Commercial Expansion

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

Job summary

Tailscale seeks a gritty, thoughtful Sales Manager to lead the Expansion sales team for the Commercial segment (<750 employees) from our new Toronto hub. The role blends high-velocity pipeline with occasional large opportunities, including $50,000-$100,000+ ACV contracts, and requires building the function from the ground up.

As the first sales leader in Toronto, you will coach account executives, establish best practices for pipeline generation, and partner with marketing, product, and partnerships to accelerate growth and deliver exceptional customer outcomes.

Qualifications

• 1+ year of sales management experience in a B2B SaaS/Software company.
• Ability to lead from the front and coach a team using data and metrics.
• Excellent written and verbal communication skills.
• Willingness to travel to industry events quarterly.

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.

Skills

Sales leadership

B2B SaaS

Communication

Travel readiness

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 is 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

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