Sales Development Representative (Outbound)

About Tailscale

Tailscale is pioneering a new era of the Internet by creating software that enables secure and seamless interconnection between people and their devices, regardless of location. Whether for individual hobbyists or global enterprises, Tailscale's platform safeguards networks and facilitates access to internal tools. Founded in 2019 with a fully distributed team, the company is supported by prominent investors such as Accel, CRV, Insight, Heavybit, and Uncork Capital.

Role Overview

In the role of Outbound Sales Development Representative, you will be essential in generating qualified business leads for Tailscale. You will manage a targeted list of accounts, driving new business through proactive outbound outreach across multiple channels, including phone, email, and LinkedIn.

This is distinct from inbound lead qualification roles; success depends on actively initiating conversations, engaging prospective clients, and creating opportunities for Account Executives.

Key Responsibilities

• Generate qualified sales leads by delivering high-volume outbound prospecting via phone, email, LinkedIn, and other methods.
• Conduct thorough research on target accounts to identify decision makers in engineering, IT, security, and executive roles.
• Create customized outreach messages addressing the specific challenges and priorities of potential customers.
• Manage a portfolio of accounts and implement strategic account-based prospecting tactics.
• Collaborate closely with Account Executives to build pipeline and support territory plans.
• Arrange quality discovery meetings for the sales team.
• Develop expertise on Tailscale's platform, client base, and competitive environment.
• Consistently achieve or surpass goals related to activity, pipeline development, and scheduled meetings.
• Utilize advanced sales tools such as Salesforce, Gong, LinkedIn Sales Navigator, Apollo, and AI-supported prospecting solutions.
• Contribute ideas and best practices to enhance team effectiveness.

Candidate Profile

• Preferred experience: Minimum 1 year in sales, business development, recruiting, or other client-facing roles.
• Excellent communication skills, both written and verbal.
• Comfortable dedicating substantial time to making outbound calls.
• Strong organizational abilities and capacity to manage a broad prospect portfolio.
• Competitive spirit, resilience, and goal-oriented motivation.
• Curiosity, coachability, and a drive for ongoing self-improvement.
• Strong work ethic with ambition to develop a career in technology sales.
• Availability to work onsite in Vancouver office at least three days weekly.

Additional Qualifications (Preferred)

• Experience with SaaS sales or outbound prospecting.
• Familiarity with Salesforce, Outreach, Gong, Apollo, or LinkedIn Sales Navigator.
• Interest or experience in selling to technical audiences, cybersecurity, networking, or cloud infrastructure.
• Bachelor's degree or equivalent professional experience.

Measures of Success in Your First Year

• Regular generation of qualified sales pipeline.
• Confident engagement with technical, IT, and security leaders.
• Mastery of modern outbound sales strategies across communication channels.
• Thorough understanding of Tailscale’s offerings and client use cases.
• Foundation for advancement into roles like Account Executive or sales leadership.

Why Choose Tailscale?

• Join a rapidly expanding infrastructure software company.
• Work with skilled sales leaders invested in your growth.
• Learn cutting-edge outbound sales techniques and tools.
• Career path with clear opportunities for advancement in enterprise SaaS sales.
• Collaborate within a supportive, high-achieving team that values curiosity, ownership, and continuous development.

Compensation and Benefits

Tailscale ensures equitable and competitive compensation including base salary, equity, and comprehensive benefits. The offered pay range for this role in Canada is a target on-target earnings (OTE) between $107,200 and $120,600 CAD, inclusive of base and variable components tied to quarterly sales goals.

Additional Perks and Support

• An inclusive culture that values diverse voices and offers flexible work arrangements.
• Comprehensive group benefits with no waiting period covering health, vision, dental for employees and their families.
• Mostly remote work environment with options for co-working space access and in-person social events.
• Employer-matched retirement contributions up to 0.75% of eligible compensation annually.
• Opportunities for in-person connection including retreats and team off-sites internationally.
• Support for personal development with $1500 USD per year for training, mentorship, coaching, and promotion opportunities.
• Flexible paid time off policy accommodating various personal needs.
• Home office setup support including choice of company laptop, monthly internet reimbursement, and $500 USD for workspace customization.
• Generous paid parental leave with top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Commitment to Accessibility and Fair Hiring

Tailscale is devoted to accessible and fair hiring practices and provides accommodations during recruitment on request. The company employs AI-assisted screening but all hiring decisions are human-made.