Remote Account Executive – Upsell & Renewals

Tailscale; Toronto; Hybrid; CAD 181,000 - 221,000; Full time

Benefits offered by this job

Base salary + equity

Remote first company

Competitive benefits package

Professional development allowance

Job summary

Tailscale is seeking a Customer Account Executive to expand and renew current customer accounts. You will upsell, educate clients on new features, and drive adoption across your portfolio, partnering with Solutions Engineering, Customer Success, Support, Marketing and Product teams.

The role is based in Toronto, hybrid (3 days in-office). You will manage multiple opportunities, present to executives, and contribute to a high-growth software startup in the Developer Security space.

Qualifications

• Experience with quota carrying or closing in a software sales role.
• Proven ability to present to senior leaders and executives.
• Strong multi-opportunity management skills across stages.
• Experience in product-led growth (PLG) motions is a plus.

Responsibilities

• Become an expert on how Tailscale helps customers.
• Build a credible pipeline through upsells and renewals.
• Own upsell and renewal numbers across assigned accounts.
• Educate customers on value during evaluation and adoption cycles.
• Generate short-term results while maintaining annual pipeline coverage.
• Provide accurate weekly forecasting and revenue delivery.
• Create mutual action/success plans with customers to expand usage.
• Participate in video-recorded customer meetings for training and quality.

Skills

Quota carrying

Executive presentations

Opportunity management

PLG sales experience

Tools

Gong

Job description

Tailscale is seeking a Customer Account Executive to expand and renew current customer accounts. You will upsell, educate clients on new features, and drive adoption across your portfolio, partnering with Solutions Engineering, Customer Success, Support, Marketing and Product teams.

The role is based in Toronto, hybrid (3 days in-office). You will manage multiple opportunities, present to executives, and contribute to a high-growth software startup in the Developer Security space.