Sales Development Representative (Outbound)

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. Job Description As an Outbound Sales Development Representative, you'll play a critical role in generating new business opportunities for Tailscale. You'll own a portfolio of target accounts and create qualified pipeline through outbound prospecting across phone, email, LinkedIn, and other sales channels.

This is not an inbound lead qualification role. Success comes from proactively opening doors, engaging new prospects, and creating opportunities for our Account Executives. You'll work closely with experienced sales leaders, receive ongoing coaching, and develop the skills needed to build a successful career in SaaS sales.

Key Responsibilities

Generate qualified sales opportunities through high-volume outbound prospecting using phone calls, email, LinkedIn, and other channels. Research target accounts and identify engineering, IT, security, and executive decision makers. Develop thoughtful, personalized outreach that resonates with customer challenges and business priorities.

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. Consistently meet or exceed activity, pipeline, and meeting goals. Leverage modern sales technologies including Salesforce, Gong, LinkedIn Sales Navigator, Apollo, and AI-powered prospecting tools.

Share ideas and best practices that improve team performance.

What We Are Looking For

1+ years of sales, business development, recruiting, or other customer-facing experience preferred Excellent verbal and written communication skills Comfortable spending a significant portion of your day making outbound phone calls Strong organizational skills and the ability to manage a large portfolio of prospects Competitive, resilient, and motivated by achieving goals Curious, coachable, and eager to continuously improve Strong work ethic with a desire to build a career in technology sales Ability to work from our Vancouver office three days per week #LI-Hybrid

Nice To Have

Experience in SaaS sales or outbound prospecting Experience with Salesforce, Outreach, Gong, Apollo, or LinkedIn Sales Navigator Experience selling to technical audiences or an interest in cybersecurity, networking, or cloud infrastructure Bachelor's degree or equivalent professional experience What Success Looks Like In your first year, you'll: Consistently generate qualified pipeline for the sales organization. Become confident engaging engineering, IT, and security leaders. Master modern outbound sales techniques across phone, email, and social selling.

Develop deep knowledge of Tailscale's products and customer use cases. Build the foundation for future growth into an Account Executive or other revenue leadership role. Why Tailscale?

Join one of the fastest-growing infrastructure software companies. Work alongside experienced sales leaders who are invested in your development. Learn best-in-class outbound sales methodologies and modern prospecting tools.

Build a career in enterprise SaaS sales with clear opportunities for advancement. Collaborate in a supportive, high-performing team that values curiosity, ownership, and continuous improvement.

Compensation

practices within our team across all roles and all levels.