Sales Development Representative (Outbound)

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. 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.

About the Role

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.

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 salary, an equity incentive plan and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
• Remote first company —most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities. 
• Paid time off and a healthy work-life integration.  Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! 
• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own. 
• Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit .