Sales Development Representative; Outbound) Hybrid British Columbia)

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.

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, Linked In, 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.

• Generate qualified sales opportunities through high-volume outbound prospecting using phone calls, email, Linked In, 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, Linked In Sales Navigator, Apollo, and AI-powered prospecting tools.
• Share ideas and best practices that improve team performance.

• 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

• Experience in SaaS sales or outbound prospecting
• Experience with Salesforce, Outreach, Gong, Apollo, or Linked In Sales Navigator
• Experience selling to technical audiences or an interest in cybersecurity, networking, or cloud infrastructure
• Bachelor's degree or equivalent professional experience

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.

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)

$107,200 - $120,600 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• A competitive total compensation package. This includes a base…