Sales Development Representative (Outbound)

About Tailscale

Tailscale offers secure and simple connectivity software that links people and their devices no matter their location. Established in 2019 and fully distributed, the company is supported by leading investors such as Accel, CRV, Insight, Heavybit, and Uncork Capital. Their mission is to create a future Internet experience that is safe, sensible, and user-friendly.

Role Overview

The Outbound Sales Development Representative (SDR) is essential in building new business opportunities through proactive outbound prospecting. Unlike inbound roles, this SDRep initiates contact with potential customers across various channels including phone calls, emails, LinkedIn, and more. This position involves managing a set of target accounts, conducting personalized outreach, and effectively setting up discovery meetings for Account Executives.

Key Responsibilities

• Generate qualified sales leads through persistent outbound prospecting efforts by phone, email, LinkedIn, and additional platforms.
• Research and identify decision makers such as engineers, IT professionals, security leaders, and executives within target accounts.
• Create personalized and insightful outreach approaches aligned with customer challenges and business goals.
• Manage a portfolio of accounts implementing account-based prospecting strategies.
• Collaborate closely with Account Executives to build sales pipelines and execute territory-based plans.
• Schedule and coordinate high-quality discovery meetings for the sales team.
• Gain deep knowledge of Tailscale’s products, customer base, and competitive landscape.
• Consistently achieve or exceed assigned goals related to activity, pipeline, and meetings.
• Utilize modern sales technologies such as Salesforce, Gong, LinkedIn Sales Navigator, Apollo, and AI-driven prospecting tools.
• Contribute ideas and best practices to enhance team effectiveness.

Candidate Profile

• Preferably 1+ year of experience in sales, business development, recruiting, or other customer-focused roles.
• Strong verbal and written communication capabilities.
• Comfortable dedicating significant time to making outbound cold calls.
• Effective organizational skills to manage a broad portfolio of prospects.
• Highly competitive, resilient, and goal-oriented mindset.
• Curious, coachable, and motivated toward continuous learning and self-improvement.
• Strong work ethic with a clear passion for a career in technology sales.
• Willingness to work onsite in the Vancouver office three days weekly.

Preferred Qualifications

• Experience with SaaS sales or outbound prospecting is beneficial.
• Familiarity with Salesforce, Outreach, Gong, Apollo, or LinkedIn Sales Navigator is advantageous.
• Background or interest in selling to technical audiences, cybersecurity, networking, or cloud infrastructure sectors.
• A bachelor's degree or equivalent professional experience is valued.

Success Milestones

• Build a consistent pipeline of qualified prospects within the first year.
• Gain confidence engaging with engineering, IT, and security leadership.
• Master modern outbound sales tactics across phone, email, and social media channels.
• Develop strong expertise in Tailscale’s offerings and customer use cases.
• Lay the groundwork for advancement into Account Executive or other sales leadership roles.

Why Join Tailscale?

• Be part of one of the fastest growing infrastructure software companies.
• Work with experienced sales leaders committed to your personal development.
• Learn industry-leading outbound sales methodologies and cutting-edge prospecting tools.
• Advance your career in enterprise SaaS sales with clear growth opportunities.
• Collaborate within a supportive, high-achieving team culture valuing curiosity, ownership, and continuous enhancement.

Compensation & Benefits

Tailscale is dedicated to equitable and competitive pay across all roles. The compensation for this role includes a base salary, equity incentives, and variable commissions based on quarterly targets. The Canadian on-target earnings (OTE) range from $107,200 to $120,600 CAD. Benefits include comprehensive group health, vision, dental coverage with no waiting periods, employer-matched retirement contributions, and paid parental leave programs.

Work Environment & Perks

• An inclusive, flexible workplace enabling authenticity and diverse perspectives.
• Remote-first company culture with options for in-person collaboration where necessary.
• Annual company retreats, team offsites, and opportunities for in-person engagement globally.
• A professional development allowance of $1500 USD annually plus mentorship and coaching.
• Flexible paid time off policies supporting work-life balance.
• Customizable home office setups with choice of company laptops and reimbursements for internet and workstation expenses.

Accessibility & Hiring Process

Tailscale is committed to an accessible hiring experience and provides accommodation on request during recruitment. Their hiring process incorporates AI-assisted tools for initial screening, but human decisions govern all hiring outcomes. Communications from Tailscale recruiting will only be sent via official @tailscale.com, @greenhouse.io, and @interviews.modernloop.io addresses. Candidates should stay vigilant against impersonation scams.