New Business Account Executive

About the Company

Tailscale is creating a simpler and safer internet by offering software that helps people and their devices connect securely, regardless of location. Its platform is used by hobbyists and large enterprises alike to secure networks, share access to internal systems, and more. Established in 2019 and operating as a fully distributed company, Tailscale is supported by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Role Overview

Tailscale is hiring motivated sales professionals for its New Business Account Executive team. This is an opening focused on new customer acquisition rather than account management. You will receive inbound leads through a round-robin system, while also being expected to build about one-third of your own pipeline through prospecting. The role covers the complete sales journey, from first contact through deal close, with a strong emphasis on earning customer confidence throughout the process.

The company has an active presence on communities such as Hacker News, X, and Reddit, and serves more than 100,000 monthly active users, including engineering leaders at highly innovative organizations. This is a chance to join an early-stage, fast-scaling startup and help shape its approach to startup sales.

Key Responsibilities

• Generate new revenue by identifying the right contacts at prospective accounts, explaining Tailscale’s value, and guiding them toward success with the product.
• Test new approaches, adapt quickly, and use market and customer insights to shape outreach and campaign strategy.
• Represent Tailscale at local meetups and larger industry events, either by traveling or coordinating attendance, to promote the company to potential buyers.
• Serve customers across multiple time zones and maintain responsiveness across regions.
• Keep activities, pipeline, and forecasts organized and up to date in Gong and Salesforce.

What We Are Looking For

• At least 1 year of experience in prospecting or closing, preferably in a door-to-door or in-person sales environment.
• The drive to create and improve a sales playbook, rather than simply follow an existing one.
• Some technical knowledge or genuine interest in technology.
• Strong communication and presentation abilities.
• A proactive, thoughtful approach to outreach and closing; candidates are encouraged to contact the hiring manager directly with a compelling explanation of why they are a strong fit, instead of submitting a routine application.
• Experience generating your own opportunities, multi-threading accounts, and moving customers from discovery to closed-won outcomes with senior technical stakeholders such as VP Engineering, CTO, Head of Platform, and CISO.
• Based in Vancouver, with a strong preference for hybrid work and 3 days per week in the office.

Compensation

The target pay range for this role in Canada is CAD 134,000 to CAD 167,500 in on-target earnings, which includes base salary plus variable compensation tied to quarterly sales target attainment. Individual offers may differ depending on experience and skill set. The overall compensation package also includes base pay, equity, and benefits.

What We Offer

• An inclusive and flexible workplace that supports authenticity and work-life integration.
• A competitive total rewards package with base salary, equity incentives, and commission for quota-carrying roles.
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for employees and their families.
• A remote-first culture, with most teams working fully remotely and access to coworking options such as WeWork or similar spaces near you.
• Opportunities for in-person connection through company retreats, off-sites, and collaboration with teammates across Canada, the United States, and the United Kingdom.
• Annual professional development support of USD 1,500, along with mentorship, coaching, and internal growth opportunities.
• Flexible paid time off to support personal needs and travel.
• Home office support including a company-owned laptop, monthly internet reimbursement, and USD 1,000 to set up your workspace.
• Parental leave top-ups available from day one for up to 26 weeks.

Accessibility and Hiring Information

Tailscale is committed to an accessible and inclusive hiring process. Candidates who need accommodations during recruitment or for any aspect of the role can contact their recruiter. The company also uses AI-assisted tools in screening and assessment, while final hiring decisions are made by people.

Security Notice

Emails from the talent team will only come from official company and approved recruiting domains. Applicants are encouraged to stay alert for impersonation or scam attempts.