Sales Development Representative

About the role

Join Tailscale as an Outbound Sales Development Representative and drive new business growth. You will manage a set of target accounts, generating qualified sales opportunities through proactive outreach. This role focuses on creating new pipeline, not just qualifying existing leads, by engaging prospects and setting up meetings for Account Executives. You will own the full cycle of outbound engagement, from initial contact to meeting booking, ensuring that every interaction moves the funnel forward. Success in this position requires a proactive approach to identifying and solving customer problems before they even recognize them. You will act as the primary point of contact for new prospects, shaping the first impression of Tailscale in the market. The role demands consistent curiosity and a data-driven mindset to refine tactics and improve results over time. You will be a growth catalyst for the company by expanding our presence in new and existing segments.

Key facts

What you'll do

• Generate qualified sales opportunities through high-volume outbound activities via phone, email, and LinkedIn.
• Research target companies to identify key decision-makers in engineering, IT, security, and executive roles.
• Craft personalized outreach messages that address customer challenges and business priorities.
• Manage a portfolio of accounts and implement account-based prospecting strategies.
• Collaborate with Account Executives to build pipeline and execute territory plans.
• Schedule high-quality discovery meetings for the sales team.
• Become knowledgeable about Tailscale's platform, customer base, and competitive landscape.
• Meet or exceed activity, pipeline, and meeting targets consistently.
• Utilize sales technologies such as Salesforce, Gong, LinkedIn Sales Navigator, Apollo, and AI prospecting tools.
• Contribute ideas and best practices to improve team performance.
• Maintain a meticulously organized pipeline that reflects true buyer intent and likelihood to purchase.
• Partner with marketing to provide feedback from the field that shapes future campaigns and messaging.
• Track and report on key metrics including response rates, reply velocity, and demo conversion.
• Act as an extension of the sales leadership team by ensuring that every interaction aligns with the broader revenue strategy.

Requirements

• 1+ years of experience in sales, business development, recruiting, or other customer-facing roles.
• Excellent verbal and written communication abilities.
• Comfortable making a significant number of outbound phone calls daily.
• Strong organizational skills to manage a large number of prospects.
• Competitive, resilient, and goal-oriented mindset.
• Curious, open to coaching, and committed to continuous improvement.
• Strong work ethic and a desire to build a career in technology sales.
• Ability to work from the Vancouver office three days per week.
• Must be legally authorized to work in Canada without sponsorship.
• Reliable transportation to the Vancouver office is required on assigned days.
• Willingness to adhere to company policies and procedures as they apply to remote and in-office work.
• Comfort with a quota-carrying role that demands consistent performance and accountability.
• Willingness to follow structured sales methodologies while retaining the flexibility to adapt to evolving buyer behavior.
• Commitment to maintaining the confidentiality of customer and company information at all times.

Nice to have

• Experience in SaaS sales or outbound prospecting.
• Familiarity 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.

Practical notes

• This role offers a competitive total compensation package including base salary, equity, and comprehensive benefits.
• Employer-funded retirement contributions match dollar-for-dollar up to 0.75% of eligible compensation annually.
• Professional development allowance of $1500 USD per year.
• Flexible paid time off program.
• Home office setup includes choice of company-owned laptop (Mac or PC), monthly internet reimbursement, and $500 USD for workstation customization.
• Paid parental leave program: 20 weeks for birthing parents, 16 weeks for non-birthing parents.
• Hybrid role requiring 3 days per week in the Vancouver office.
• Tailscale is committed to an accessible and inclusive hiring process; accommodations can be requested.