Sales Development Representative (Outbound) - Tailscale

About Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

About the Role

As an Outbound Sales Development Representative, you'll play a critical role in generating new business opportunities. You will own a portfolio of target accounts and create qualified pipeline through outbound prospecting across phone, email, LinkedIn, and other channels. This is a proactive role focused on opening doors and engaging new prospects.

Key Responsibilities

• Generate qualified sales opportunities through high-volume outbound prospecting.
• Research target accounts and identify engineering, IT, security, and executive decision-makers.
• Develop thoughtful, personalized outreach that resonates with customer challenges.
• Own a portfolio of accounts and execute account-based prospecting strategies.
• Partner closely with Account Executives to build pipeline and execute territory plans.
• Schedule high-quality discovery meetings for the sales team.
• Become an expert on Tailscale's platform, customers, and competitive landscape.
• Leverage modern sales technologies including Salesforce, Gong, LinkedIn Sales Navigator, and Apollo.

What We Are Looking For

• 1+ years of sales, business development, recruiting, or customer-facing experience.
• Excellent verbal and written communication skills.
• Comfort with high-volume outbound phone calls.
• Strong organizational skills and ability to manage a large portfolio.
• Competitive, resilient, and goal-oriented mindset.
• Ability to work from our Vancouver office three days per week.

Why Tailscale?

• Join a fast-growing infrastructure software company.
• Work with experienced sales leaders invested in your development.
• Learn best-in-class outbound methodologies and modern tools.
• Clear opportunities for advancement into Account Executive or revenue leadership roles.
• Comprehensive benefits, equity, and a supportive, high-performing culture.